I am probably biased because it is my hometown, but Chicago is one of the best places to visit in the USA. Many first timers travel to Chicago for a weekend trip, so I have put together a guide for first time visitors that only have 2 days or less. There is so much to do in Windy City, but here are the best things to do if you only have 36 or 48 hours in Chicago including what to see, where and what to eat, where to drink and where to stay in Chicago. I am including both the popular tourist attractions as well as a few off the beaten path suggestions.
36 to 48 Hours in Chicago Itinerary
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36 to 48 Hours in Chicago Things To Do
This is a fairly packed 2 day Chicago itinerary so if you enjoy exploring at a more relaxed pace check out my one day in Chicago itinerary.
1) Visit Millennium Park and The Bean
If you have seen photos of Chicago on instagram or facebook, chances are you have seen photos of Cloud Gate (which most people call The Bean), the famous mirrored sculpture in Millennium Park. Millennium Park is a free attraction and is a portion of the Grant Park. In addition to Cloud Gate, Millennium Park also includes the Jay Pritzker Pavilion, the Crown Fountain sculpture and Lurie Garden.
Although the Bean is very very touristy, don’t skip it. It is one of the most instagrammable places in Chicago and it is a great spot to take some selfies to remember your trip to Chicago. Millennium Park is usually crowded especially in the summer and on weekends so to avoid the crowds visit early in the morning.
In the summer, kids and some adults love to splash at Crown Fountain. In the winter, there is a free ice skating rink right in front of the park.
Tip: If you are traveling with children, you might also want to check out Maggie Daley Park, a large public park located between Millennium Park and Lake Michigan and connected to Millennium Park by the BP Pedestrian Bridge. Features include a fieldhouse, climbing wall, an ice-skating ribbon in the winter, mini-golf and several different play areas for kids.
2) Check out the Art Institute of Chicago and other great museums
Chicago has many great museums which are worth visiting. Depending how much you enjoy museums, you might want to spend some time in one of more of them when visiting Chicago.
The Art Institute of Chicago is my top pick and is conveniently located next to Millennium Park. It is one of the oldest and largest art museums in the United States and is frequently found on lists of the top museums in the world. (Click here to buy a skip the line ticket if you want to avoid long lines).
The Museum of Science and Industry is located in in Hyde Park and is a bit out of the way from downtown Chicago but it is a really fun museum with hands-on activities and interactive exhibits.
3) Take an architecture river cruise or walk along the Chicago Riverwalk
Chicago has amazing architecture and the best way to see it is by taking an architecture river cruise. There are several companies that offer tours but the best one is the one from the Chicago Architecture Foundation (CAF). The 90 minutes cruises are run by CAF-certified volunteer tour guides. Because the river freezes in the winter, cruises run only between April/May and November.
An alternative to a river cruise is to take a walk along the Chicago Riverwalk. The Riverwalk is one of the best spots in Chicago for people watching and there are also restaurants, shops and places to sit along the way. You can also hop on a water taxi here.
4) Enjoy the view from above
One of the best ways to see Chicago is to check out the view from one of its tall buildings. Chicago has two skyscrapers with observation decks (a third observatory has been proposed).
360 CHICAGO (formerly John Hancock Observatory) on the 94th floor of the 875 North Michigan Avenue (the building formerly known as the John Hancock Center) has TILT an enclosed moving platform that tilts you out over Michigan Avenue from the 94th Floor. If you are over 21, you can go up two floors and get the same view at The Signature Lounge at the 96th for the price of two drinks.
5) Hang out at Navy Pier
Update: Navy Pier has temporarily closed to the public starting September 8, 2020 and will reopen spring of 2021.
Personally I am not a big fan of Navy Pier as it can be somewhat of a tourist trap but it is a must do if you are visiting Chicago with toddlers or kids. There are fun attractions at Navy Pier including a Ferris wheel, restaurants, shops, an IMAX theatre, the Chicago Children’s Museum, and the Chicago Shakespeare Theater. Navy Pier is also the starting point for various sightseeing tours and cruises.
Tip: If visiting Chicago in the summer, you might want to check out the free fireworks at Navy Pier every Wednesday and Saturday night.
6) Explore the lakefront and beaches
Chicago’s Lakefront Trail is an great way to see Chicago and enjoy incredible views. Chicago’s Lakefront Trail is a paved path on a 18-mile-long stretch along Lake Michigan and it is a great spot to people watch and get some exercise. In the summer and weekends, the lakefront is packed with locals and visitors walking, running and riding bikes.
Most people don’t think of Chicago as a beach destination but Chicago has many beaches along the lake. The most popular beaches are located downtown (Oak Street and North Avenue) but they are also the busiest. Two of the best beaches for more of a local feel include Kathy Osterman Beach and Foster Avenue Beach which are both located north of downtown.
7) Lincoln Park
Another free attraction, Lincoln Park lies along the lakefront. Lincoln Park is large but first time visitors should focus on the section adjacent to the Lincoln Park neighborhood which contains the Lincoln Park Zoo, Lincoln Park Conservatory, Theatre on the Lake, a rowing canal, the Chicago History Museum, the Peggy Notebaert Nature Museum, the Alfred Caldwell Lily Pool and the North Pond Nature Sanctuary. The Lincoln Park Zoo is one of the oldest zoos in North America and one of the only zoos in the US with free admission.
8) Watch a Cubs Game at Wrigley Field (or attend another sporting event)
Chicago is known for their love of their sports teamss, so if you have time and enjoy sports you might want to attend a sporting event. To those unfamiliar, historic Wrigley Field is home to one of the city’s baseball teams – the Cubs. Whether a fan of the Cubs, baseball in general or just a lively atmosphere, a day at the 100 year old ballpark is a must for locals and tourists alike. You don’t need to enjoy baseball to enjoy a Cubs game – it is fun to just soak in the atmosphere while drinking and eating. If you want to see Wrigley but are unable to attend a game, you can sign up for tours of the stadium during the off season.
Get off the beaten path: If you visit Wrigley check out Alta Vista Terrace District a historic district in Lake View located two blocks north of Wrigley Field. The one-block street was built in 1904 in imitation of the rowhouse style of London.
9) Go to a Festival
There is almost always one or more festivals or events going on each weekend. Some Chicago festivals are very well known and attract tons of visitors, but there are many festivals and events in Chicago where you will mostly see locals. For great food, music and people watching, check to see if there are any festivals or events going on while you are in town.
10) Walk The 606
The 606 is Chicago’s version of The Highline in NYC, an elevated trail goes through 2.7 miles of the city’s northwest side neighborhoods: Wicker Park, Bucktown, Humboldt Park, and Logan Square. It is a bit off the beaten tourist path but it great place to walk, run or bike. There are several access points so you can get off the trail to explore the various neighborhoods.
What and Where to Eat in Chicago
Chicago is one of the best cities in the world for food and I could easily write a whole post just about the food! Although Chicago is famous for food like deep dish pizza and Chicago-style hot dogs – there is so much more great food in Chicago. Don’t limit yourself to just deep dish pizza and hot dogs, but you should try those if you are visiting Chicago for the first time.
Here are some of my recommendations for where to eat if you are a first time visitor to Chicago.
Deep dish pizza – The best restaurants for deep dish pizza in downtown Chicago include Lou Malnati’s and Giordano’s but they are very busy especially on weekends and in the summer so expect long lines during peak hours – so long you will see people waiting outside on the sidewalk. Many locals love Pequods in Lincoln Park which is said to have the best deep dish pizza in Chicago.
Chicago-style hot dog – Grab a Chicago-style hot dog for lunch (remember, no ketchup allowed). Portillos is a popular spot.
Chicago Style Popcorn – For popcorn head to Garrett Popcorn Shops. There are several locations including Navy Pier and Michigan Avenue.
Steaks – Chicago is full of great steakhouses. My top pick for first time visitors to Chicago is Gibsons Bar & Steakhouse, a Chicago classic in the Gold Coast, and it has great people watching and you might even spot a celebrity. Another less well known option (but still busy) which gets great reviews is Bavette’s Bar and Boeuf.
Burgers – Many people claim that Au Cheval has the best burger in Chicago if not in the US. Personally, I don’t like to make claims that something is the best because obviously I have not tried every burger but I think it is very good. They don’t take reservations and the wait is often up to 2 hours long! Fortunately, they do use an app where you can track your spot in line so you can leave and come back (there are plenty of bars nearby where you can wait).
Ethnic – Chicago is a city of immigrants and some of them own restaurants which means Chicago has restaurants serving pretty every cuisine in the world. I recommend trying some of the great ethnic food that Chicago is well known for. Little Italy and Greektown are very close to downtown Chicago and easy to visit. You can also take the water taxi to Chinatown from the Riverwalk. One of the best places for Mexican food are the food vendors at Maxwell Street Market on Sunday mornings. There are many more options, including Polish and Indian food, not as close to downtown Chicago.
Foodies – Foodies will love Chicago as there many great restaurants with well known chefs. In fact, BonAppetit, just named Chicago the restaurant city of the year for 2017. I like Girl & the Goat and its sister restaurant Little Goat (Executive Chef is “Top Chef” winner Stephanie Izard). Tip: Many of the top restaurants are reserved weeks ahead of time, so if you have your stomach set on one, make a reservation in advance.
Where to Drink in Chicago
Chicago has great nightlife so if going out for drinks is your thing you won’t be disappointed. If you visit in the summer, outdoor rooftops decks are extremely popular.
Some great spots for drinks or food with views include J Parker, a bar and restaurant on the rooftop of the Hotel Lincoln with 180 degree views of the lakefront, LH Rooftop with great views of the river and Cindy’s rooftop restaurant overlooking Millennium Park and Lake Michigan.
One of the best views of Chicago both day and night are from The Signature Lounge at the 96th at the former John Hancock.
Where to Stay in Chicago
The possibilities are endless but most people visiting Chicago stay in the downtown area including the Loop, River North, Gold Coast, Streeterville and Michigan Avenue since they are close to most of the major tourist attractions. If you are visiting during the weekend, the Loop is a great option as it is more quiet at night. River North (where I live), is close to nightlife and restaurants, but street noise can be a problem especially during the weekends.
If you want to stay somewhere with more of a local neighborhood feel, consider staying at a hotel or Airbnb in Wicker Park, Lakeview or Lincoln Park but you will have to use public transportation or a taxi/uber/lyft/bike to visit most of the tourist attractions.
Here are some of my top picks for the best hotels in Chicago:
The Peninsula Chicago. If you are looking for a luxury hotel, The Peninsula Chicago is one of the best hotels in Chicago with a world renown spa and a half-Olympic length swimming pool overlooking the Chicago skyline. It has a central and convenient location right off the Magnificent Mile, close to shopping and less than a block from the John Hancock. Click here to see the latest prices.
Hilton Chicago/Magnificent Mile Suites. Recently renovated all-suite hotel with fridge and microwave in room. Great location just steps from Michigan Avenue and one block from Lake Michigan. Click here to see the latest prices.
ACME Hotel Company. This is a new, modern, stylish and unique hotel located in downtown Chicago 2 ½ blocks from the Magnificent Mile in River North. Offers great value and great service. Click here to see the latest prices.
Best Western River North Hotel. Convenient located in the heart of River North close to the Chicago River as well as many restaurants and bars. Amenities include free high-speed Wi-Fi, deeply discounted parking, room service, fitness center, indoor pool and sun deck. Click here to see the latest prices.
Majestic Hotel. Majestic Hotel is a bit out of the way from the major tourist attractions but it is located less than a mile from Wrigley Field in a nice residential part of Lakeview. Offers great value as well as free breakfast, wi-fi and in room fridge. Click here to see the latest prices.
Chicago Travel Tips
When is the Best Time to Visit Chicago?
Chicago has plenty of things to do year round – both indoors and outdoors. Winters can be freezing some days but I think winter is a great time to visit Chicago because accommodation is cheaper and the popular tourist attractions are less crowded. Summer is the busiest time and usually has great weather (but some days can be very hot and muggy). The nice thing about visiting in the summer is that are always festivals, concerts and events going on around the city in the summer. Spring and fall are generally great times to visit – the weather is usually more pleasant and not as busy as summer. Spring temperatures vary and can be less predictable but I think fall generally has the best weather. Still need help deciding when to go to Chicago? Check out The Best Time to Visit Chicago – A Month By Month Guide.
Getting There and Around
Downtown Chicago (where most of the tourist attractions are) is very walkable and you don’t need a car to get around. For longer distances use public transportation, and taxis, Lyft and uber are plentiful and easy to find. You can also rent bikes through Divvy, Chicago’s bike share program, or take a water taxi.
Other Chicago Tips
Bring a mask. According to Illinois law, everyone over the age of 2 who can medically tolerate a face covering over their nose and mouth must wear one at a public place when unable to maintain a safe distance (6 feet) from others. While you are OK to walk outside without a mask and most people do, most indoor attractions will not allow you in the premises unless you are wearing a mask or face covering.
These are my top choices for the best things to do in Chicago if you only have 36 or 48 hours.
Have you visited Chicago? If so what would you recommend first time visitors see if they only have 2 days in Chicago?
Looking for more inspiration for visiting the United States? Check out some of our other USA travel guides and itineraries:
- The Ultimate USA Travel Bucket List: 100+ Best Places to Visit in USA
- Weekend In New York City: The Perfect Itinerary for 48 Hours in NYC
- Weekend in Las Vegas: The Perfect Itinerary (According to a Local!)
- 2 Days in San Francisco Itinerary
- 3 Days in Los Angeles: The Perfect Itinerary
- Weekend in Kansas City Itinerary
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