If you’re looking for an itinerary to help you navigate your upcoming 2 days in Chicago, you’ve come to the right place! Our 2 days in Chicago itinerary will help you hit as many top destinations in the city while inhaling some culture and history on the way. Here, we’ll equip you with the know-how and insider tips to help you get around in a breeze so that you can make your trip as effortless as a vacation ought to be.
Chicago is a relentless, innovative metropolitan hub in the center of the American Midwest with culture and mentality of its own. The “Windy City” is known for its groundbreaking city planning, its skyscrapers (with famous architects like Frank Lloyd Wright), and its financial and commerce centers. And of course, in pop culture, Chicago’s also known for its prohibition characters like Al Capone, its deep-dish pizza, improv comedy, and its contribution to countless music genres.
After the Great Chicago Fire destroyed most of the town is 1871, the resilient community was able to quickly rebuild itself out of its ashes, but this time from stone, steel, and with the help of new technologies. Soon afterward, the 1893 Colombian exposition showcased the city’s bold intentions to create a “city beautiful,” which were also incorporated into the 1909 plans of Chicago. One result of this plan has become Chicago’s ever-growing green spaces and parks!
The city that pioneered American city planning has continued to routinely make ground-breaking technological and architectural achievements, including that of the Chicago canal, which revered the flow of the Chicago River, and the construction of the world’s first skyscraper (in the 1880s!), and many architectural schools of thought. The city is a hub for creativity and innovation!
2 Days In Chicago Itinerary
Day 1 – The Historic River North
Your first day in Chicago is primarily centered on and above the Chicago river!
Stop 1 – The Willis Tower and John Hancock Center
Your 2 days in Chicago, the city that birthed the modern skyscraper, must include at least one stop inside one of its tallest skyscrapers! Of the two noteworthy skydeck options in Chicago, most tourists will end up visiting the Willis Tower (formerly the Sears Tower) because it’s the tallest, and most well known of the Chicago skyscrapers. In fact, it’s also the tallest observation deck in the United States! Bringing in over 1.3 million visitors a year, you’ll want to arrive here as early as possible to avoid long lines!
The Willis (Sears) Tower Skydeck is located on the 103rd floor of the 110-storied building, and offers panoramic 360-degree views of the city! The Willis (Sears) building is located on Wacker avenue in the heart of downtown. On a good day, one can see into the distance for miles, even into the neighboring states. And of course, it’s one of the best views of Chicago’s downtown, navy pier, and Lake Michigan. In addition, the Skydeck offers a feature called “The LEDGE,” a series of glass boxes extending 4 feet out from the building. The experience is fun and unique, though it may require waiting in line for your turn!
If not for the view, the Willis Tower is worth a visit if just for its historical significance in the city of Chicago and the world. The Willis Tower was built in 1974 as the Sears Tower and served as Sears’ headquarters, then the world’s largest retailer of over 350,000 employees! The company moved out in 2009, and the building was subsequently renamed Willis Tower after Willis Group Holdings.
The 1,454-foot-tall skyscraper was the tallest building in the world for 25 years until 1998 and is currently the second tallest in the United States. And of course, this skyscraper is especially iconic to Chicagoans because this city was made important contributions to the development of the modern skyscraper, including the first skyscraper in the world, which was constructed in the 1880s (it has since been deconstructed).
The Skydeck entrance is accessible from Jackson Boulevard, which can be reached easily by the famous “L” line in the famous downtown loop district. Because it’s likely the lengthiest time commitment of the tourist attractions in Chicago, it’s ideal to get this stop out of the way as soon as it opens. Be prepared to wait! On a busier day, the waiting time may exceed 2 ½ hours! If it’s not possible to arrive in the day (e.g. the weather isn’t ideal) the crowds will generally begin to diffuse after 5 pm. From March to September, the Skydeck’s hours span from 9am to 10pm, while from October to February they are 10 am to 8 pm.
Single entry tickets will cost $26 for adults and $18 for children.
A second Skydeck opportunity that many tourists aren’t aware of is located in the 875 North Michigan Avenue Building, more often referred to as the John Hancock Center (its previous name). Lying next to lake Michigan at the top of the Magnificent Mile, this tower is 100 stories tall and offers a Skydeck called “360 Chicago” on its 94thfloor. A special feature this viewpoint offers is TILT, a moving glass platform that leans visitors over the edge of the skyscraper at a 30-degree angle! Other than having the TILT feature over the Willis’ Ledge, the John Hancock building’s “360 Chicago” Skydeck is, in essence, the same experience and an excellent alternative for anyone who just wants to capture an amazing view of the city without the wait. The line up can sometimes be as short as 5 minutes, and is almost never more than an hour!
The John Handcock Center can be reached via the red metro line and is located at the top of the famous Magnificent Mile on Michigan Avenue. Ticket prices are comparable to Skydeck’s at $22 for adults, $ 15.00 for kids, and a $44 fast pass.
When it comes down to it – both are amazing experiences, and we’d highly recommend trying both out both sky decks if time permits! For ambitious travelers, 2 days in Chicago is just enough time to see both!
Whether you prefer Chicago 360 or the Skydeck, we highly recommend purchasing a Chicago CityPASS, a bundle of Chicago’s most popular attractions that will save your wallet while visiting Chicago. Of course, you’d want to visit at least three of the included locations to make the bundle worth your while.
Stop 2 – Architecture Boat Tour
After having waited in long lines, doesn’t a boat ride down the Chicago river sound nice? Chicago is world-famous for its architecture, and this is exactly why you can’t pass up a Chicago Architecture Cruise on your 2 days in Chicago! Whether history or architecture is of any interest to you, these cruises are a wonderful way to kick back and relax while quickly hitting the top tourist destinations. Offering a full-service bar and snack bar, an hour and a half tour might be the very best opportunity to capture the skyline’s views, and of course, to take some great photos.
Cruising down the Chicago River, you’ll be able to see the Navy Pier, the Willis Tower, the John Hancock Center, Millennium Park, the Historic Water Tower, and many more. Many of the skyscrapers on the Chicago river represent the cutting edge of art form in skyscrapers when they were built, a legacy that’s continued to draw famous architects into the city today as much as before.
Although there are quite a few companies that offer architecture tours, we recommend the original tour run by the Chicago Architecture Company. They offer a wide selection of departure times (every 30 minutes after 9 am until 5 pm) when the weather is appropriate. Lasting an hour and a half each, they’re run by volunteers from Chicago’s Architectural Center and are operated via Chicago’s First Lady Cruise ships. These tours depart from 112 E. Wacker Drive, next to the Chicago Architecture Center.
For up-to-date schedules, check out their official website
At the time of writing, tickets are $46.29 per person for daytime cruises and $51.02 for twilight cruises. Tickets are best bought online to avoid lines and sellouts and are best purchased a day or two before the tour to avoid bad weather (tickets can’t be refunded). Another bonus to buying tickets through this company is the cheap extra $5 add-on offer that allows guests to access the museum at the Architectural Center!
And of course, if an architectural tour isn’t your cup of tea but you still want to take a boat ride, that’s totally fine! Chicago operates water taxis, and they’re far more fun than the ones that drive! It’s fairly inexpensive, and a great practical alternative to just get around!
Stop 3 – Navy Pier
Iconic for its large Ferris wheel and family-oriented facilities today, the 3300-foot-long pier on the shoreline of Lake Michigan hasn’t always been Chicago’s premier amusement park destination. “Municipal Pier” opened in 1916 and served as a dock for passenger arrivals, freights, and for indoor and outdoor expositions.
The pier was probably best remembered for its association with the navy. Renamed “Navy Pier” in 1927 to honor the naval veterans of the First World War, it subsequently served as the training center for the United States Navy between 1941 and 1946. It wasn’t until 1995 that the pier began to rebrand itself as an amusement park and first incorporated a Ferris wheel into the park. In 2016, the park celebrated its centennial birthday, erecting a new Ferris wheel, among many other new attractions.
This wheel, like the one before it, has always been the main draw to the park because of the incredible skyline views it offers and also just because it’s in Chicago! The world’s first Ferris Wheel was a 250ft towering novelty chosen to serve as the focal point of the 1893 Columbian exposition in this city, just a year after the Eiffel Tower was featured in the previous world fair. Although not standing at the same location, this new 2016 Centennial Wheel celebrates the amazing legacy of this city! The ride is just $15 when you get your tickets in person, however, if you’re traveling during the summer or over the holidays it’s a good idea to book them ahead of schedule to avoid some awful lines. Find your online tickets at Get Your Guide!
Since turning over into a non-profit organization in 2011, Navy Pier and has heavily redeveloped and rebranded itself to better outfit what has become such an important civic landmark in the United States.
Other than beautiful shorelines, and an amazing city skyline, the Pier compromises of an amusement park, a children’s museum, a Shakespeare Theater, an IMAX theater, an indoor botanical garden, a beer garden with live performances throughout the week, and stages set up specifically to serve local community organizations. Navy Pier has really become a “people’s pier,” an urban oasis where the community is able to play, learn, and celebrate its diversity! Whether you have kids, or you’re an adult traveling by yourself, Navy Pier has so much to offer, and shouldn’t be overlooked on your 2 days in Chicago.
Stop 4 – The Magnificent Mile
Get ready to walk! The magnificent mile, a nickname referring to the upscale shopping district on the northern end of Michigan Avenue in Chicago, is one of the must-see streets in downtown Chicago! As the most successful shopping district in Chicago, the area is comparable to New York’s 5thavenue or Rodeo Drive in Beverly Hills. The area boasts the 8thhighest rent in the country and is scoured with high-end hotels, restaurants, and expensive brand names like Versace, Burberry, Tiffany’s and Cartier.
The commercial district features some of the tallest skyscrapers in the city including the former John Hancock Center, the Wrigley buildings, and the Tribune Tower. The street is also home to the popular Historic Water Tower that famously survived the Great Chicago Fire of 1871.
The retail street was partially imagined in the 1909 Burnham Plan for Chicago but didn’t begin achieving some potential as a retail and commercial center until the Michigan Avenue bridge was constructed in 1920. The area then slowly gained more prominence over the decades as the mid-range historic loop shopping district in downtown Chicago continued to lose its customers base to suburban shopping centers.
As the Chicago Loop’s target shopping population started moving from the city center and into the suburbs, the city of Chicago began to lose its reputation as a shopping destination altogether. Luckily, the magnificent mile’s ideal location in the city’s commercial district had an accessible reach to the city’s affluent population, who continued to commute into the business hub on a daily basis.
It wasn’t until the construction of the Water Tower Place in 1975 (a multipurpose construction including a shopping mall and movie theater) that the magnificent mile reached the height of glory, marking the return of retail prominence in the city.
Whether to shop or to merely look around, the Magnificent Mile is undoubtedly a memorable destination you’ll want to see on your 2 days in Chicago. This street has become a staple in the city and a popular tourist destination! The beautiful rising architecture and the historic water tower are on its own worth a visit to see!
For those interested in architecture, consider taking a walking tour down the Magnificent Mile.
Stop 5 – Riverwalk
Our next stop has increasingly become one of the most popular hang-out spots in the city and is another great example of a newer extension of city that follows one of its great traditional legacies – its waterways.
Chicago owes its livelihood to its rivers, its position on the continent, and its proximity to Lake Michigan and the Mississippi River. 1848 saw the completion of Chicago’s first canal, which would open the entire Midwest to an economic boom. Similarly, the early 20th century’s “Chicago Sanitary and Ship Canal” famously reversed the flow of the connecting Chicago river in order to improve the sanitation of the city. These engineering feats helped the city earn its reputation for ingenuity.
In a similar spirit, the city of Chicago recently completed a decades-long Riverwalk project in 2016 that sought to make the Chicago’s primary river more meaningful, sustainable, and intuitive by opening up the riverside of the Chicago River to the public. The $98.6 million projects created walking paths in the heart of the city and merged local businesses with nature to create the ultimate urban oasis! The project is an extension of a larger one that’s amplified the philosophy that the city has grown up on, one that envisioned a garden inside a city.
While on the riverwalk, take the opportunity to stop at a café and sit outside for a bit! It’s also a great location for dinner, or a late-night walk when the city can be enjoyed lit up and reflected against the water. As one of the hottest new spots for locals to relax, this spot can’t be missed when you spend 2 days in Chicago!
Stop 6 – See a Show!
Alongside New York City, Chicago has one of the most active theater scenes in the United States. Home to over 200 small independent theater groups and a hoard of theaters supporting traveling Broadway shows, this city a great stop for anyone who loves the theater! The city has long held a creative tradition of producing up and coming Broadway musicals, experimenting with off-broadway theater, and showcasing famous traveling Broadway shows! Don’t forget to see a show on your 2 days in Chicago!
Most Broadway musicals in downtown Chicago today are run through theaters belonging to the production company called Broadway in Chicago, owned by the Nederlander Organization. This group is the second-largest operator of legitimate theaters and music venues in the US, only after the Shubert Company that established Broadway in New York City. Therefore, you’ll be able to find broadway tickets through the Broadway in Chicago website, or through Ticketmaster.
Most of these shows are today performed in historic theaters like the James M. Nederlander Theatre, the Cadillac Palace Theatre, the CIBC Theatre, and Auditorium Theatre, as well as the more recently constructed Broadway Playhouse Theater.
Some other theater companies to consider for off-Broadway shows are The Goodman theater, an excellent non-profit community theater with quality productions in the heart of downtown, the Shakesphere theater at Navy Pier, or the Steppenwolf Theater company in Lincoln Park. Additionally, the “Drunken Shakespeare” act by The Drunk Shakespeare Society has been a popular show because it involves a unique level of audience interaction!
Finally, Chicago is the city behind the modern improv movement! The Second City, a theater troupe started by a group of university students in 1952, has raised generations of comedians for the popular SNL TV comedy series in the US, and SCTV in Canada, both of which are very reminiscent of the Chicagoan comedy style which began with a mix of theater games and rehearsed skits. Having evolved greatly through the years, this theater group is still at the frontline of developing great new comedians! Check out the Second City’s performances at their new location on 230 West North Avenue.
Whichever option is of most interest to you, you absolutely can’t miss seeing a show when you spend 2 days in Chicago!
Day 2 – Museums and the Historic Loop District!
Day 2 of your 2 days in Chicago is all about exploring the historic downtown area, including the “loop” district and the city’s amazing museums! Your first stop of the day, Millennium Park, opens at 6:00 am, and is best visited fairly early to avoid the crowds. No one really wants a “Bean” picture 200 other people in the frame!
Stop 1 – Millenium Park
As one of the most relaxing, and most iconic spaces in Chicago Today, you’ll want to arrive here before the crowds come, but late enough to have enough sunshine in your photos. Don’t be afraid to sit down for a while and enjoy the sun! 8 am is usually early enough to beat out the crowds.
Millennium Park is one of the most beautiful spaces in the entire city! The park was designed to upgrade the city into the 21st Century, while still aligning its ethos with the city’s legacy as an “Urbs in Horto,” or a “city in a garden.” This park is so important within the city because it was designed to serve the needs of its current and future generations of residents while celebrating its diversity. The park was a major addition to the city and has been considered by many unprecedented since the legendary 1893 Columbian Exposition!
Millennium Park is in itself the largest landscaped terrace in the world, having been built atop a parking garage and railway tracks (today Millennium Station). The park, an extension of the larger Grant Park, has many attractions and monuments including a cycling center, a war veterans memorial, a welcome center, 2 performance stages, one permanent restaurant, a garden, and many pavilions with dedicated art.
The main attraction to the park, which may be the most iconic structure in Chicago, is located above the only permanent restaurant in the park and known locally as “The Bean.” Officially called “Cloud Gate,” the 23 million-dollar 3-story reflective steel sculpture comprises of 168 welded steel plates that evenly cover the bean-shaped structure, offering viewers a unique mirror-view portrait of the city. Another unique element to the structure is its concave underside, which warps multiple reflections like a kaleidoscope. The unique monument poetically fuses the viewer into the historic yet modern cityscape and is a powerful reminder of the complex, diverse world we live in, as it literally reflects every person who approaches it. Aren’t we all part of the city’s narrative?
Another powerful interactive work of art in the millennial park is the Crown Fountain. Two transparent towers with water flowing down its faces collect water in an adjoining granite reflecting pool. Behind the surface of each tower, LED lights to display a digital video depicting a set of 1000 faces belonging to Chicagoans. Water flows from each mouth, symbolizing life. When the weather is nice, dozens of children can be seen playing in the pool! What better way celebrate diversity than to build a space for that community?
Finally, the Lurie Gardens (sometimes called the “hidden gardens”) on the south side of Millennium park consist of a combination of perennials, bulbs, grasses, shrubs, and trees. The garden is split into 2 sections, one representing Chicago’s past with shade-loving plants and trees, and the other with sun-loving perennials representing Chicago’s future. This botanical park, in particular, pays tribute to the city’s motto as an “Urbs in Horto,” or a city in a garden.
Millennium Park is known for being extremely accessible, in part because it was designed to be used however people see it fit! In this likeness, it serves its residents by hoisting year-round cultural performances and events in its indoor and outdoor stages, and on its multi-purpose pavilions. Located just off the city’s historical district, and sitting next door to the Art Institute of Chicago, the park is the perfect spot for tourists to relax between activities and a great space for college students and business employees to relax on lunch break. You’ll love this space on your 2 days in Chicago because it really a perfect place to run into locals and tourists alike! Don’t forget to stop at the park’s scenic outdoor Plaza Café for a quick bite or drink!
A bridge on the south side of Millennium park connects directly to the Art Institute, our next destination!
Stop 2 – Art Institute of Chicago
The Art Institute of Chicago is an important museum for everyone to explore because its exhibits, its legacy, and traditions have been the backbone of Chicago’s art scene for ages. It’s also the most popular museum in Chicago! The world-class museum is one of the largest in the country, featuring one of the world’s best collections of Impressionist and post-impressionist paintings in the world. Famous artists represented in the collection include Seurat, Monet, Georgia O’Keefe, Van Gogh, Matisse, Jackson Pollock and Andy Warhol. You’ll also be able to find artwork from all around the world here, and of course, works from Frank Lloyd Wright – a native to the region and a great contributor to Chicago’s famous architecture.
A renowned city of commerce, Chicago has also always carried with it an interest in the arts. Beginning in 1879, the Art Institute began showcasing some of the world’s finest classical and impressionist art and even included pieces from some local artists like Mary Cassett. Afterward, the fair’s only permanent building, the “Beaux-Arts Palace” located on Michigan Avenue, would become the first permanent home to the Art Institute and its first original collections.
The art movement in Chicago would slowly begin to mature, despite its being so far away from the rest of the art world. Because local artists were suffered early on in comparison to master artists in Europe, they began adapting into an anti-mainstream attitude that’s persisted in many ways today. These Chicago artists championed the abstract movement in the 1920s and the Imagist movement that began to define the city’s art scene by the 1960s.
Unlike other art hubs, Chicago’s commercial district has always played an active role in the city’s art education, especially through the School of the Art Institute of Chicago’s Design program. These programs have generally complemented the interests of local businesses, who (like the local government) have poured their money into them. These benefactors have always encouraged new and unique philosophies of art theory that would help fuel artistic growth, and creativity. This focus on innovation allowed all parties to flourish, commercially and artistically.
Today Chicago’s art scene is arguably the most diverse and one of the most distinguished in the country, owing much of its success to the famous Art Institution. Art in Chicago is today still inextricably conceptual and design-oriented. To learn more about art and its place in Chicago, you absolutely have to explore the Art Institute of Chicago Museum on your 2 days in Chicago!
For the best deals on admission, don’t forget to purchase a CityPASS!
For more information visit the Art Institute’s official website here
Stop 3 – The Field Museum
The Field Museum of Natural History (generally referred to as the Field Museum) is another noteworthy museum you’re going to want to visit on your 2 days in Chicago. The museum is one of the best natural history museums of its kind, and very engaging for all ages. The museum was established in 1893 as the Columbian Museum of Chicago, though its current namesake takes after Marshall Field, the large retail mogul of the early 20th century who donated a substantial amount of funding into the institution at his height.
Today the museum is one of the most successful, most reputable, and largest of the Natural History museums of its kind in the world with over 2 million visitors a year. In particular, the museum is renowned for the quality of its educational and scientific research programs and its state-of-the-art interactive exhibits. It’s also famous for attracting popular traveling exhibits, for which it owes much of its foot traffic.
The Field Museum has an impressive permanent collection, with over 24 million specimens and objects belonging to its research and display collections that include fauna, gems, meteorites, fossils, and anthropological/archaeological artifacts. In addition, the museum includes a library of over 275,000 books, journals, and photo archives.
Some of the most famous exhibits here include the Egypt exhibit, featuring multiple mummies, a replica of a Mauri meeting house, and the famous SUE T.Rex skeleton that formerly stood inside the great main hall of the museum until she was moved to make room for a casted replica of the world’s largest dinosaur, Maximo the Titanosaur.
Just south of the Art Institute from Grant Park, the Field Museum is located on Chicago’s Museum Campus at 1400 South Lake Shore Drive and can be easily accessed by foot (or public transportation). Tickets for adults are $24 for adults residing in the state of Illinois, and $26 for those out-of-state, while child admissions are priced at $17 for residents aged 3-11, or $19 for out-of-state. However, the cheapest way to see this museum and others is with the Chicago CityPASS bundle!
Stop 4 – State street area/ historic loop shopping district
You haven’t seen the city until you’ve seen Chicago’s historic downtown district! The area is bound between Lake Street in the North, State street in the West, Wells Drive in the South, and Wabash in the South. Traditionally the premier shopping district in Chicago and the center of the city, no other area has more buildings registered under National Historic Landmarks or Places. The area was also famous for introducing the “L” that became the namesake of the “Loop district.”This system of tracks was built above the streets and designed to support the popular shopping market by cutting down on taxing traffic and transporting shoppers in and out of the area efficiently. Your 2 days in Chicago should essentially gravitate in and around this central area.
After the Great Chicago Fire in 1871, State Street was considered to be the center of downtown and therefore still comprises of the city’s oldest and most noteworthy buildings, including the former Marshall Fields building and Sullivan Center. At its hiatus, the area consisted of over 7 large department stores! But when retail centers began hitting the suburbs by the 1950s, the importance of the Loop retail district began to dwindle and continued to do so through the decades until just recently. During that time, the Magnificent Mile began to take prominence over the retail culture in the city because it was located in the commercial district of the city, which affluent suburban residents would have had access to between commuting.
One of the best streets for shopping today is still State Street, where you’ll also be able to find the Chicago Theater with its iconic “Chicago” marquee. The Sullivan Center, although no longer home to the Carson Pirie Scott retail store (it’s now Target), still stands to display the beautiful architectural motifs designed by Louis Sullivan, as does the famous Marshall Fields building that houses Macy’s today.
Today, the historic loop shopping district is one of the liveliest areas of the city, filled with university students, and new residents have spilled into the area by the opening of new apartment spaces and offer a mix of popular restaurants, cafes, and affordable clothing brands. It’s absolutely beginning to embrace the youth that’s returned to and reclaimed the historic areas of the amazing city!
Don’t know where to begin? Consider taking a tour of the Loop District! Here are our top picks!
Take a tour inside Chicago’s most photographed theater, the Chicago Marquee Theater!
Tour the city’s oldest buildings in the historic loop district
Tour historic interior architecture in this loop district tour
Where To Stay In Chicago
Other than being right around the corner from Millennium Park and the Art Institute of Chicago, this hotel has one of the most stunning historic interiors in Chicago. The hotel pays homage to the extreme opulence bequeathed by its celebrity owners, the Palmers, in the late 19thcentury. The hotel’s stunning vaulted ceilings and frescoes can be viewed from its lobby, bar, and lounge. As one of the longest operating hotels in America, the Palmer House has had its share of famous guests from Ulysses S. Grant to Mark Twain and Judy Garland. A hotel is still a place of luxury today! The majority of this building dates to the 1920s, when 14 stories were added to the lower structure, and has been heavily renovated over the last few decades.
Royal Sonesta Chicago Riverfront
Located on the waterfront of the Chicago River on Wacker Drive, no location could possibly be more perfect than this one for 2 days in Chicago. In the center of downtown Chicago, guests here are showered with the absolute best views of the famous river, and able to commute easily between all corners of downtown, such as the Navy Pier and Museum Campus. The hotel has comfortable modern interiors.
Originally designed by the famous Chicago architect Daniel Burnham in the late 19thCentury, this chic boutique hotel tastefully blends modern trendiness with a bit of nostalgia. Marble floors, mosaics, mahogany doors, and an early hydraulic elevator accent the otherwise bright and crisp furnishings of the hotel. This plot of land was purchased by William Ellory Hale, who owned a hydraulic elevator company and dreamt of building a skyscraper to showcase his vision. Built during the same era as the Columbian Exposition, this iconic skyscraper, completed in 1895, was similarly built with white terracotta large glass windows and built to function as a dentist’s office. Today, the hotel is located in a perfect location, immediately next to State Street in the Loop District.
Congress Plaza Hotel
Located on Michigan Avenue, just across from the Buckingham Fountain and Millennium Park, this hotel has both budget and location on its side. Adjacent to the Museum Campus and Millennium Park, this hotel is particularly convenient on your second day of our 2 days on the Chicago trip. The Congress Plaza Hotel is a historic hotel dating to the 1920s with cozy interiors and modern furnishings.
Cambria Hotel Chicago
Located within the same complex as Chicago’s famous historical Oriental theater (the James M. Nederlander theater as of 2019), this trendy boutique hotel boasts a great location with a little bit of history. This hotel puts you in the center of Chicago’s entertainment district! The location also offers easy access to Chicago’s museums, the city’s oldest architecture, and the Chicago River.
Getting To Chicago
For those arriving in Chicago from outside of the Midwest, one of the easiest ways to get into Chicago will be by plane. The largest airports in the immediate Chicago area are the O’hare airport and Midway airport. As the 3rd busiest airport in America, O’hare is far more likely to deliver cheaper flights into the City solely because it offers more. However, the advantage of Midway is a smaller airport with fewer crowds and shorter lines, and of course a shorter commute into the city.
From O’hare, one of the cheapest ways to get into the downtown area is by train. Chicago’s “Blue Line,”operated by CTA Trains, allows you to skip on the expensive uber/taxi ride into the city, or burden of renting a car (and driving a car) to only to pay large wads of cash per hour to keep it parked. This train will cost about $5 and take 45 minutes to reach downtown Chicago.
From Midway, the same can be achieved by taking the “Orange Line,” costing only $2.50 for the 25-minute ride. Otherwise, many hotels in Chicago offer shuttles that pick up guests from the airport every 10-15 minutes! If your hotel doesn’t offer pick-ups, there are many shuttle services, including GO Airport Shuttle, that operate to drop hotel guests off at their destinations for a fee.
For those who are coming into Chicago from the Midwest, driving is a great option. However, cars make for a very large burden in downtown Chicago. Luckily, Chicago is known for having a great rail system that extends to the far ends of the state of Illinois. Therefore, it’s very easy to park your car at a small train station outside of the city (for free!) and take the train into the city (Chicago’s Union Station, or OTC). This way, you’ll avoid having to drive in the city’s infamously terrible traffic and dodge hefty parking fees.
How To Get Around In Chicago
The downtown area of Chicago is an incredibly walkable environment, so finding a centrally-located hotel that allows you to walk is so important for your 2 days in Chicago. Ubering or taxiing is notoriously expensive and inconvenient in Chicago.
Some rides can take 30 minutes to an hour to arrive at your location in popular areas. However, this is nothing to worry about! There’s so many options at your disposal! Once you’ve arrived at your hotel (assuming it’s located downtown), walking and public transportation (the “L”, metra, and river taxis) will become your preferred forms of transportation!
Chicago is a city that’s filled to the brim with tenacity and edge. The city is celebrated with diversity, a thriving arts and entertainment culture and dynamic architectural. Its downtown is at the center of this celebration. With the help of our 2 days in Chicago itinerary, you’ll be able to glimpse into the history and landscape of Chicago, and bring you back to see more.