36-48 Hours in Chicago: A Perfect Itinerary (Written By A Local!)

36 – 48 Hours in Chicago: Things To Do, Where To Stay & Where To Eat! Keep Reading for all of the Windy City’s Highlights to make help plan your weekend trip.

Ready for a weekend in Chicago? Of course you are! Who doesn’t love to spend time in the Windy City?! Whether you’re looking to pack everything into one jam-packed weekend or pick your highlights from Chicago’s Top Things To Do, we’ve got options and ideas to suit every budget and every style of traveler.

From Museums to Planetariums,  Gangster tours to Signature Bars, you can build your own itinerary to make sure you get the best from your 36 hours in Chicago or 48 hours in Chicago. And with recommendations for where to stay and what to eat – we’ll have your weekend break to Chicago organized before you know it!

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A Guest Post by Alannah McEwan from Itchy Feet Travel

Chicago is the third biggest city in the USA and the fourth biggest in North America so there’s lots of tourist attractions to see and do. So what if you only have 48 hours or even 36 hours in Chicago? How can you make the most of those two days?

I’m going to share with you the 10 best things to do in Chicago, suggestions for where to stay and some must try foods to make sure you get the best from your weekend away! 

RELATED: Struggling with what to pack? Check out our Ultimate Travel Packing List (with free pdf printable!) to make sure you pack everything you need!

Essential Chicago Travel Tips: What to Know Before You Go

The Best Time To Visit Chicago IL

The best time to visit Chicago is during Spring and Fall if you are looking for mild temperatures and sunshine. The warm weather makes it easier to walk around and explore the city;  or from September through the end of October wherein the temperatures are warm and hotel rates are reasonable prices. 

How To Get Around Chicago IL

Chicago is too big to navigate using only your own two feet. The best way to get around is via public transportation – specifically the L train (short for ‘elevated train’!).

Identified by colors (red, blue, brown, green, orange, purple, pink, and yellow), the L system provides extensive and speedy service to 145 stations around town (including the city’s two airports). 

If you want to take a trip to the Chicago suburbs, Metra is your most reliable friend. The system’s 11 lines extend outward from the Loop, making stops in North, East, and South Chicago before heading on to nearby communities like Evanston, Aurora, Joliet, and University Park.

If you plan to use Metra over the weekend, you can purchase a weekend pass which gives you unlimited travel on weekends.

Also, if you happen to be traveling as a large group, it is better to opt for dedicated transport – such as GOGO Charters – over public transport. This means you’ll be able to give your group set departure times (and for those that have done large group travel, know that keeping everyone on schedule can be a nightmare!) and make sure you get efficiently from one attraction to the next.

Where to Stay in Chicago IL

Looking for some great hotel deals in Chicago take a look at Booking.com or HotelsCombined, or take a peek at our recommendations for some great hotels in Chicago, whatever your budget!

Luxury Stay ($250+ per night): Thompson Chicago (Read Trip Advisor Reviews)

Strategically located in the heart of the city, this 4-star hotel makes for an ideal base in Chicago. It is located a brief stroll from John Hancock Center Observatory, Chicago Water Tower and Michigan Avenue.
After a day of sightseeing in the region, guests can unwind in the comfort of their air conditioned rooms. They all offer movies on demand and a mini bar.

Mid-Range Stay ($150-$250 per night): Westin Chicago River North (Read Trip Advisor Reviews)

Conveniently situated, The Westin Chicago River North offers easy access to Chicago’s main tourist attractions. It has a spa and wellness center, as well as a kids club, 24-hour room service, and valet parking.
Featuring modern rooms equipped with a mini bar, tea, and coffee-making facilities, and a refrigerator. They also offer a range of entertainment amenities, such as movies on demand.

Budget Stay (<$150 per night) Best Western River North (Read Trip Advisor Reviews)

Offering views of Chicago, Best Western River North Hotel is conveniently situated in Downtown Chicago, close to a popular shopping district, plus boasts a rooftop terrace and an indoor pool.
Attractions near Best Western River North Hotel include Michigan Avenue, the Chicago Theater, and Magnificent Mile. Its central location offers easy access to sightseeing, dining and entertainment.

48/36 Hours in Chicago: Things to do

Architecture River Cruise

A great way to see the city and learn some history at the same time is by doing a boat tours or river cruise. I did the architecture tour and it lasted 75 minutes.

I got to see a lot of the city during this tour as well as learn about major events that have shaped the city and the different styles and types of architecture that make Chicago what it is today. It is one of the best Things To Do in Chicago.

Chicago Riverwalk

The Chicago Riverwalk is a beautiful waterfront area that runs along the south bank of the Chicago River in the heart of the city. It features a variety of restaurants, bars, and other recreational and entertainment options. Visitors can take a leisurely stroll along the river, stop to enjoy a meal or a drink, or rent a kayak or boat to explore the waterway.

The Chicago Riverwalk is a popular destination for tourists and locals alike, offering a respite from the hustle and bustle of the city and a chance to enjoy the beauty of the river.

Magnificent Mile

A great and free thing to do in Chicago Illinois is to take a walk down magnificent mile (aka Michigan Avenue). It’s one of the best know areas of downtown Chicago.

Michigan Ave/Magnificent Mile mile is 13 blocks that stretches from the Chicago River to Oak Street and is lined with shops, restaurants, and beautiful buildings. Wandering the Magnificent Mile is one of the best things to do in Chicago this weekend.

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Navy Pier

Another great place for a walk in Chicago is Navy Pier. In the summer months it’s buzzing with people and energy.  Also, during the summer there are fireworks every Wednesday and Saturday evening. The pier was built 100 years ago in 1916 and is now one of the city’s most popular tourist’s sites.

Millennium Park

 This 24.5-acre park is packed with attractions. While you’re there check out Frank Gehry’s Pritzker Pavilion and serpentine bridge, sculptor Anish Kapoor’s 110-ton Cloud Gate (also know as the bean) and Jaume Plensa’s Crown Fountain.

The Lurie Garden has year-round flower displays and monthly garden walks.

Art Institute of Chicago

 There are many museums in the city, but only one that’s been rated by TripAdvisor as the Best Museum in the World. The AIC is the perfect way to enjoy the indoors on a rainy or chilly day.

You could easily spend all day here and still not see everything, so if you’re on a time crunch decide which exhibitions interest you the most so that you make the most efficient use of your time. You could even grab a Fast Pass to skip the lines.  Personally, I thought the miniature rooms were pretty cool, the amount of details was unbelievable!

*Bonus* Chicago has loads of great museums and festivals to experience throughout the year including:

• The Museum of Science and Industry;
• Chicago History Museum;
• The American Writers Museum;
• The Museum of Contemporary Art Chicago; and
• The Field Museum of Natural History
  (all of the above are open all year round) PLUS
• The Chicago International Film Festival which is held in June each year.

Shedd Aquarium

 The aquarium is 75-year-old institution. Here you will find piranhas, frogs, snakes, rays, turtles, eels, predator sharks and much more! 

Signature Lounge on the 95th Floor

Whether you have 36 hours in Chicago or 48 hours in Chicago, to get an unbeatable view of the city head to the Signature Room. It’s on the 95th floor of the John Hancock building. Don’t forget to go to the bathroom where you will get the best view! We probably spent just as much time in the bathroom as we did in the lounge! 

Indulge Your Inner Foodie in the West Loop

The West Loop is an area of Chicago that is a food lover’s paradise, with a diverse array of live music, rooftop bars and dining options to choose from.

From fine dining restaurants featuring world-class cuisine, to casual eateries serving up delicious, affordable fare, the West Loop has something for every taste and budget.

Many of the restaurants in the area source their ingredients locally, and there is a strong emphasis on sustainability and supporting the local food community.

Whether you’re in the mood for a fancy dinner out or a quick bite to eat, the West Loop has you covered.

Lincoln Park Zoo

The Lincoln Park Zoo is the oldest zoo in the USA! It is also one of the only free zoos in the country. Here you can see all types of animals from apes to zebras, and overall, the zoo has more than 1,000 animals!

Chicago Mob Tour: Criminals and Gangsters

Escape into the criminal past of Chicago. This Mob Tour will take you to River North, Gold Coast, Lincoln Park, Old Town, and Magnificent Mile districts. Chicago is famous for it underworld of gangsters and mobsters and you can learn about all them from a local expert. Hear stories about Scarface, Al Capone, The Untouchables, the Chicago Mob and more!

Enjoy the Outdoors at Maggie Daley Park

Maggie Daley Park is a popular destination located in the heart of downtown Chicago. It features a range of recreational activities, including a climbing wall, ice skating ribbon, mini golf course, and playground.

The park also has beautiful green spaces, perfect for picnics or a leisurely stroll, and is great if you just want to people watch! With its central location and a wide variety of amenities, Maggie Daley Park is a favorite spot for both tourists and locals alike.

Adler Planetarium

Go on a trip to the moon at the Adler Planetarium. This was the first planetarium in the United States and includes a real research observatory and a space theatre. There really is no need to wonder what to do in Chicago with all these suggestions for the the best things to do in Chicago!

What and Where to Eat and Drink In Chicago

Enjoying your 36 hours in Chicago (or 48 hours in Chicago) is as much about what you do as what you eat.  You’ve just gotta try these three Chicago favorites:

Deep Dish Pizza

 I asked locals and tourists alike about where to get the best deep dish pizza in Chicago. The two names I heard the most was Giordano’s and Lou Malnati’s. I chose to try Lou’s on my trip. I ordered the calamari fritti, buffalo chicken wings, and of course their famous deep dish pizza with sausage and extra cheese.

Everything was tasty and the portions were a good size. The pizza was piled high with toppings and the staff was friendly and attentive. Definitely, a must eat in Chicago! Two thumbs up!

Chicago Style Hot Dog

Next on the list of tasty things to do in Chicago is to eat a Chicago style hot dog from any of the cheap eats around the city! I didn’t even realize before my trip that Chicago had their own unique style of hot dog.  This dog is windy city favorite.  

Topped with yellow mustard, green pickle relish, tomato, a slice of dill pickle, sport pepper and celery salt. Most important is what’s not on the hot dog … ketchup! The kiosk where I picked up my dog even had a sign that said if you want ketchup you have to dance for it!

Chicago Style Popcorn

For Chicago style popcorn you’ve got to try Garretts. There are several locations in the city, I stopped and got a bag at their Navy Pier location. There is a variety of flavors to choose from. I went for the Garrett Mix, a yummy combination of Caramel Crisp and Cheese Corn. Two great flavors in one bag!

*EXTRA* Make some iconic Chicago-style dishes at home with these recipes for Italian Beef Sandwich & Deep Dish Pizza

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