48-hour itinerary: what to do in Chicago, the city of Pope Leo XIV
Chicago made headlines in international news on Thursday (8) after American Cardinal Robert Prevost , a native of the city, was chosen as Pope Francis’ successor. With this, the Illinois metropolis becomes the birthplace of the first pope born in the United States — a historic milestone for the Catholic Church and for the city, which can now also be called “ Pope City .”
Known as the “ Windy City ,” Chicago impresses with its harmonious contrast between nature and urban architecture . Walking through its streets is a unique experience: on the one hand, your eyes turn upwards, admiring iconic skyscrapers; on the other, it is impossible not to stop to enjoy the well-kept parks, green spaces and the famous Millennium Park.
Modern, leafy, vibrant and multicultural, Chicago offers a rich culinary scene and a vibrant cultural life. If you’re passing through the city — whether on a layover or a quick visit — it’s worth following a practical itinerary to try its typical delicacies and get a feel for its unique atmosphere.
But be careful: despite allowing for good times even in a short period of time, Chicago deserves more days on your itinerary . With influences from several metropolises and a striking identity of its own, the city invites visitors to discover it calmly and in depth.
Tourist itinerary in Chicago for those who only have two days in the city: Day 1- Breakfast: Lou Mitchell’s
Starting the day in Chicago or any city in the United States means you almost have to have a good breakfast, in the famous American style. And the city has no shortage of traditional options for this – which are popular with both tourists and locals.
We suggest starting your first day with a stop at Lou Mitchell’s . Founded in 1923, the century-old restaurant has a long tradition of serving breakfast and brunch, and is known for its generous portions.
Its extensive menu includes a variety of dishes such as pancakes, waffles, sandwiches in different flavors, eggs prepared in different ways, as well as its famous omelets, especially the “Greek Omelet”. Its French fries are also famous there. The full menu, including lunch suggestions, can be found at this link .
The place has a vintage charm, with decor that harks back to the 1920s. Depending on the time of day, you may find a huge line, but don't worry: it usually moves quickly!
Lou Mitchell's: 565 W Jackson Blvd, Chicago, IL 60661, USA/Tel: +1 312-939-3111/Hours: Wed-Fri 6am-2pm; Sat-Sun 7am-2pm. Closed Monday-Tuesday.
Very close to Lou Mitchell's is the Willis Tower , the tallest building in the city with 110 floors and over 500 meters high (including the antennas). The tip is to leave the restaurant and walk there.
The building is one of the best-known tourist attractions, both for its architecture and for housing an observatory with glass terraces (including the ground) on its 103rd floor: the SkyDeck Chicago . From there, visitors have a view that can encompass up to four states: Illinois, Indiana, Wisconsin and Michigan – a radius of 80km, depending on weather conditions.
If you want to guarantee a good photo, the place is known for its great shots. Visits are scheduled, and tickets can be purchased online or on site, depending on availability. The tip is to book in advance to plan your day better, since the times are always in high demand.
It's open every day, and if you want to see the city lit up at night, that's also possible. Adult tickets cost $44 plus tax (about R$250) and visits last 30 minutes.
Furthermore, before going up to the main attraction, a small museum on the ground floor of the building tells the history, facts and curiosities about the building, which was once the tallest in the USA, and the culture of the city.
Skydeck (Willis Tower): 233 S. Wacker Drive, Chicago, IL 60606/Hours March–September: Sunday–Friday, 9am–10pm; Saturday, 8:30am–10pm/Hours October–February: Sunday–Friday, 9am–8pm; Saturday, 9am–9pm/Tickets can be purchased at this link.
If you can't resist combining cultural activities on your trip, a stop at the Art Institute of Chicago is a must.
Located in the heart of Chicago, just one block from Lake Michigan and adjacent to Millennium Park, the Art Institute is comprised of eight buildings and covers nearly one million square feet.
Of course, the ideal would be to spend at least a good part of the day in the space, which has countless works of art in its collection, from renowned icons to lesser-known works from all corners of the world. However, if you organize an itinerary with the main items you want to see, at least it won't be left unnoticed on your itinerary.
The collection comprises around 300,000 works of art spanning up to 5,000 years of history. Its portfolio includes significant works by Monet, Van Gogh, Renoir, and Picasso, as well as important collections from the Impressionist period. There are permanent and temporary exhibitions, which can be viewed on the website.
Admission to the museum costs $32 for adults (around R$180). Children under 13 go free.
Art Institute of Chicago: 111 South Michigan Avenue/Hours: Monday, 8am-5pm; Thursday, 8am-8pm; Friday-Sunday, 11am-5pm. Closed Tuesdays and Wednesdays/Tickets can be purchased here.
- Lunch: North Beer & Cider Garden
Northman Beer & Cider Garden Riverwalk is a bar in Chicago located along the famous Riverwalk . It specializes in craft ciders and offers a wide variety of beers, both local and international.
With a beautiful view of the Chicago River, the space offers several outdoor tables (great for those who go in the summer ), live music, and a menu of snacks to share, dishes and various sandwiches. There is an option for those who want to try the famous Chicago Hot Dog , which has beef sausage, pickles, chopped onions, cucumber, mustard, tomato, and green pepper. The food menu can be found at this link and the drinks menu at this.
It is a popular spot for tourists and locals who want to enjoy the Riverwalk especially during days with pleasant temperatures.
Northman Beer & Cider Garden Riverwalk: 233 E. Riverwalk, Chicago, IL 60601/Tel.: +1 312-877-5212/Hours: Daily, 11am-11:30pm.
- Post-lunch walk to Millenium Park
Walking along the Riverwalk is a pleasant experience in itself. The promenade takes you to different bars, restaurants and activities. After trying the famous Chicago Hot Dog there, we recommend extending your walk to the Magnificent Mile to admire its iconic buildings, such as the Wrigley Building and the Chicago Tribune, one of the city's most influential newspapers.
Just a few minutes' walk away is Millennium Park, located within Grant Park , a public park in The Loop neighborhood. It is home to Chicago's most famous landmark: The Bean . The official name of this enormous metal sculpture by artist Anish Kapoor is Cloud Gate, and it is always packed with tourists and locals. A tip to avoid the peak times for the best photos is to return early the next day.
- A late afternoon drink at Cindy's Rooftop
The rooftop of the Chicago Athletic Association Hotel offers panoramic views of Millennium Park and the lake. Cindy's Rooftop Bar and Restaurant is located there.
The kitchen is run by chef Kaleena Bliss, who offers brunch, lunch and dinner menus. The drinks menu alone is over five pages long, and there are also wines and spirits available.
The venue is open every day and also hosts private events – there is both an indoor and outdoor setting. Reservations are recommended but not required.
Check out other rooftop suggestions in the city .
Cindy's at the Top of the Chicago Athletic Association: 12 S. Michigan Avenue Chicago, IL 60603 / Hours of Operation: Monday through Thursday, 11 a.m. to 11 p.m.; Friday, 11 a.m. to midnight; Saturday, 10 a.m. to midnight; Sunday, 10 a.m. to 11 p.m. / More information can be found on the website.
- Dinner: Giordano's, Uno or Lou (Have the traditional “Deep Dish Pizza”)
Once in the city, another must-try dish is the famous Chicago Pizza. Called “Deep Dish Pizza” , it looks like a pie, with a special dough and lots of filling. There are several traditional places to try it, and you will find it in different flavors and versions.
Since the dough is thick and the filling is always generous with lots of tomato sauce and cheese, it takes more than 40 minutes to prepare – so consider this in your schedule. Some of the most famous restaurants that serve it are: Giordano's , Uno Pizzeria & Grill and Lou Malnati's, which have different locations throughout the city.
- Blues at Kingston Mines to end the night
Kingston Mines is one of Chicago’s most iconic blues clubs, located in the Lincoln Park neighborhood. Founded in 1968, it offers an authentic musical experience and is known for keeping the city’s blues tradition alive. The atmosphere is relaxed, with simple decor, and attracts both tourists and locals.
There are two rooms, each with separate stages, allowing for a constant rotation of blues bands and artists throughout the night. You can expect performances from local musicians and special guests, including both well-known names and new blues talent.
Entry costs $20 (around R$112) and the menu includes typical American dishes, different commercial, craft, local and imported beers, mixed drinks and spirits. Tickets can be purchased in advance or at the box office – the tip is to arrive early to get a seat at one of the shared tables and enjoy the night in peace.
Kingston Mines: 2548 N Halsted St, Chicago, IL 60614, United States/Tel: +1 773-477-4646/Hours of operation: Thursday, 6pm-2am; Friday and Saturday, 7pm-4am; Sunday, 5:30pm-2am/More information can be found on the location's website.
Day 2- Breakfast: WildBerry Pancakes & Café
Known for its famous pancakes and classic American breakfast, Wildberry Pancakes & Café has two locations in the city, including one right next to Millennium Park. Whether you’re looking to start your day or have brunch, there are plenty of options with generous portions. Eggs prepared in a variety of ways, including hearty omelets; waffles; sandwiches and toasts; and a range of hot and cold beverage options are also available. The full menu can be found at this link.
Wildberry Pancakes & Café (Prudential Plaza): 130 E Randolph St Chicago,IL 60601/Tel.: (312) 938-9777/Hours of Operation: Daily, 7am-2pm.
- Chicago River Boat Tour (Architectural Tour)
It is impossible to talk about Chicago without mentioning its architecture. A tragic fire in 1871 devastated the city, which was full of wooden buildings. This date is remembered daily there, since it was from there that Chicago became a reference in the subject.
After seeing most of its buildings destroyed, the city received a lot of incentive and investment to rebuild itself, and, having the opportunity to start from scratch, innovative architects like Daniel Burnham and Louis Sullivan developed what we know today as skyscrapers, with resistant metal structures, which transformed Chicago into one of the cities with the most beautiful skyline in the world.
And on this boat tour along the Chicago River, you can learn a little more about the history of each iconic building. The Architecture Tour has a specialized guide who explains each important point. It is recommended to do it on days with milder temperatures, since on cold days the wind is so cold that it makes it almost impossible to enjoy the experience.
Tours usually depart from docks along the Chicago River, and there are more than one company that offers them. One of the most famous and recommended is the “Chicago's First Lady” , organized in partnership with the Chicago Architecture Foundation Center River Cruise. The trip lasts 90 minutes and there is an option to do it at night. All boats have a full-service bar and small snacks on board. Tickets start at $54 (about R$302) and it is recommended to buy in advance, selecting the desired time – there are several throughout the day .
- Field Museum (Natural History)
Located in Grant Park, the institution is dedicated to telling the natural history of the world. The museum houses over 20 million specimens in its collection, from the earliest fossils to past and present cultures from around the world. It is home to the famous Sue, the most complete skeleton of a Tyrannosaurus Rex, measuring 13m long and 4m wide.
Visitors can also explore Egyptian tombs that are over 5,000 years old. Tickets can be purchased online or at the ticket office – there are different price options.
Field Museum: 1400 S. DuSable Lake Shore Drive, Chicago, IL 60605 / Hours: Daily 9am-5pm, last admission 4pm. Closed Thanksgiving and Christmas.
Since 2012, one address in Chicago has become a must-see for anyone who enjoys a good burger: 800 W Randolph St, in the gastronomic West Loop area. That's where Au Cheval is located.
The restaurant, run by restaurateur Brendan Sodikoff, who owns eight other successful establishments in the country, including the second Au Cheval in New York, is relatively small, does not accept reservations and the lines are huge. So, here's a warning: arrive early, that is, at the time it opens, or be prepared to wait.
The reason for its success: one of the most famous burgers in the country. In fact, the publication Bon Appétit has already declared it the best burger in the United States, in addition to being a regular on several other lists and rankings. Learn more about the place . The full menus of food, drinks and desserts can be found at this link.
Au Cheval: 800 W Randolph St, Chicago, IL 60607 / Hours: Monday-Saturday 10am-11:15pm, Sunday 10am-10:15pm.
Navy Pier is also a must-see for first-time visitors to the city. In addition to being one of Chicago’s main tourist attractions, it offers a variety of experiences for all ages – many of them free – but if you’re traveling with children, it’s a must-see. The list of activities can be found on the venue’s official website.
The famous pier is located on the shores of Lake Michigan and is about 1km long. It is home to the city's Ferris wheel, the Centennial Wheel, which is almost 60m high . Gardens, shops, restaurants, boat rides, exhibition facilities, theatre and shows can also be found there. Especially in the summer and on sunny days, its facilities are packed with people admiring the beautiful view of Chicago.
- Afternoon drink at Offshore Rooftop
Located at the eastern end of Navy Pier is the Offshore Rooftop , a great place to enjoy the evening while admiring the city – there is a special happy hour menu, as well as full menus with options of dishes, appetizers and different drinks. It was recognized by Guinness World Records as the largest terrace intended for a bar/restaurant in the world. It is 4,859.78 m², with views of Lake Michigan and also of the famous Chicago skyline.
Offshore Rooftop: 1000 East Grand, Chicago, IL 60611, Festival Hall, Entrance 2, Navy Pier/Summer hours: Sunday–Thursday, 11am–10pm; Friday–Saturday, 11am–11pm.
One of the most famous venues for Chicago's jazz scene – if not the most – the Green Mill gained fame in the 1920s in the city and is located in the Uptown neighborhood. It is said that one of the most notorious regulars at the venue was Al Capone, the famous Chicago mobster. The venue was the setting for the film High Fidelity – just one of many titles filmed in the city.
The entire environment harks back to the years when it opened, and the nostalgic atmosphere is complemented by antique furniture and low lighting, with live performances of classic and modern jazz and also Poetry Slam presentations, a spoken word poetry competition.
Cover charges vary depending on the night's attractions. The venue does not accept reservations and payment is only made in cash – they do have an ATM available.
Another important point of note: there is no food on the menu, only drinks.
Green Mill: 4802 N. Broadway, Chicago, IL 60640, USA / Hours of operation: Sunday–Thursday, 4pm–1:11am (you didn’t read that wrong, they make a point of emphasizing that); Friday, 4pm–2am; Saturday, 1pm–2am.
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