48 Hours in Chicago: How to Spend a Weekend in the Windy City

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Article written by: Rebecca
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Wondering how to spend 48 hours in Chicago? Here’s everything you should add to your itinerary, from sights to fun to eating!

When visiting the third largest city in the USA, it can be a challenge to squeeze everything into 48 hours in Chicago. But, with some careful planning, it’s possible to hit the highlights!

We spent a jam-packed weekend in Chicago and it quickly became one of my favourite cities to visit in the U.S. The city has the culture and sophistication of New York – but it’s cleaner and friendlier. It’s certainly one of the coolest places to visit in the USA.

If you’re a first-timer to Chicago, or even an experienced visitor looking for some new ideas, here’s a guide of what to do, see and eat in Chicago in a weekend.

The Chicago River flanked by towering skyscrapers and a clear blue sky. Boats navigate the water as pedestrians walk along the riverwalk.
What to do and eat in Chicago

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The best things to do in Chicago mapped out

Here’s a map of everything I’ve listed in this post so you can plan your own Chicago itinerary.

Chicago in a weekend: What to see and do

Want to save money during your weekend in Chicago? Buy a Chicago CityPASS. You’ll get steep discounts on some of the best Chicago attractions. Learn more here.

Architecture river cruise

I’m certainly no architecture expert, but what I do know is that Chicago is freaking beautiful. On every corner of the Windy City you will see the vision of acclaimed architects played out in a variety of different materials and styles.

The best way to see this is from the water. Take a river cruise for a crash course in architecture and the history of the city. The 90-minute cruises are led by staff who provide entertaining and informative commentary. An absolute Chicago must-do.

Book tickets online here.

Modern glass skyscrapers reflecting the surrounding buildings and blue sky in downtown Chicago.
The unique, rounded facade of the River City condominiums with multiple balconies, set against a backdrop of other buildings and a clear sky. One of the best things to do in Chicago is to take a river cruise to see the city's architecture.

If you want to stay on the water, check out these spots where you can kayak Chicago River.

The Riverwalk

Back on land, walk the pedestrian Riverwalk, a paved, 1.25-mile-long stretch. This area was expanded in 2015 and is now home to dozens of restaurants, cocktail and wine bars, brewhouses and even a floating garden.

We walked a short section of it but were in a hurry to get to our river cruise, so we unfortunately didn’t have time to stop at all the lovely bars that were full of people enjoying the sunshine.

Millennium Park

In the heart of downtown Chicago, Millennium Park is a huge public space that’s great to visit any time of the year.

It’s home to picnic spots, public art, fountains, gardens and even rock climbing. Jay Pritzker pavilion hosts concerts during the warmer months.

Crowds gather around the reflective surface of the Crown Fountain in Millennium Park, with a giant digital face displayed on the fountain and Chicago's skyline in the background. Millennium Park is one of the must-dos if you only have 48 hours in Chicago.

It’s also where hordes gather to snap a selfie at Cloud Gate, aka The Bean. It’s fun to move around and see your distorted self in the shiny silver surface. If you want to avoid the crowds, plan to visit this popular Chicago attraction in the morning.

Tourists surrounding the Cloud Gate sculpture, also known as 'The Bean,' in Millennium Park, with the city's skyline reflected in its shiny, metallic surface. One of the most popular things to do in Chicago is visit Cloud Gate, also known as the Bean, a popular spot for taking photographs.


Chicago is located on Lake Michigan and has a number of beaches dotted around the city. It wasn’t quite warm enough for us to even dip our toe in the water, but in summer the sand is packed with beach-goers.

You can also burn off all the pizza calories (read on for this!) along the paved 18-mile lakefront trail. It’s definitely a place to add to your Chicago itinerary, no matter what time of the year.

A sandy beach with people playing volleyball and relaxing near the Lake Michigan shore, with Chicago's high-rise buildings in the distance.

Art Institute of Chicago

If you’re into art, the Art Institute of Chicago (111 S Michigan Ave) houses an enormous collection. It has in past years been voted the number one museum in the world. Art lovers could spend hours or even days wandering through each of the exhibits. It’s also a great activity for rainy days.

Here, you can also recreate your favourite scenes from Ferris Bueller’s Day Off.

It’s conveniently located next to Millennium Park.

Want a more intimate look at the Art Institute of Chicago? This tour gets you inside the museum before anyone else on a special guided tour.

Interior of the Art Institute of Chicago, featuring a grand staircase, classical architecture, and visitors admiring the artwork.

The Second City

Chicago is home to The Second City (1616 N Wells St), an improv comedy club that has launched the careers of the likes of Tina Fey, Mike Myers and Martin Short.

The club showcases some of the funniest sketches I have ever seen, and the comedians’ improv skills blew me away. Be prepared for audience participation!

A mural of 'The Second City' logo painted on a brick wall, with a spotlight and the hashtag #SecondCity below. Make sure you visit Second City on your weekend in Chicago - it's a fun night out!

Cocktails with a view

For great views over Millennium Park, stop by Cindy’s Rooftop (12 S Michigan Ave, above the Chicago Athletic Association Hotel) for a drink or a bite to eat. Yes, it’s touristy and busy, but the views are unbeatable.

The Signature Lounge (875 N Michigan Ave) on the 96th floor of the John Hancock building is also famous for its city views.

An aerial view of a lush garden in Grant Park, with colorful autumn trees, Chicago's skyline, and the blue waters of Lake Michigan in the distance.
Views from Cindy’s Rooftop

Blues bar

Chicago is one of the homes of blues music, and it’s a fun night out if you’re a music fan. As I researched, I found that most of the shows on the nights we were there were more jazz-focused, so we went to Buddy Guy’s Legends (700 S Wabash Ave) and watched a toe-tappin’ blues show from our own table.

Musicians perform on stage at a blues club with vibrant lighting, spectators enjoying the live music. Buddy Guy's Legends is a great place to add to your Chicago weekend itinerary.

Chicago bars

We didn’t get to a lot of bars on our 48 hours in Chicago (we’re getting oooold, man!) but we did stumble upon Moneygun (660 W Lake St) while we were waiting for our table at dinner one night. Intimate, with an extensive and well-priced cocktail list, it felt super secret and hidden.

Other recommended bars I found during my online research include Three Dots and a Dash (435 N Clark St), The Broken Shaker (19 E Ohio St) and The Aviary (955 W Fulton Market – bookings a must to get a seat).

Where to eat on a weekend in Chicago

Even if you’ve only got 48 hours in Chicago, you can still squeeze plenty of food in! I actually can’t believe how much we managed to eat. Here are our favourite places to eat in Chicago.

Deep dish pizza

Of course, a visit to Chicago isn’t complete without trying the famous deep-dish Chicago pizza. You can count on an argument if you ask Chicagoans for the best place. To avoid a squabble, plan on trying a few pizza joints and then make up your own mind.

After much research and wavering, we made our way to Pequod’s Pizza (2207 N Clybourn Ave). This always-busy place is known for its deep-dish pizza with a delicious caramelised crust. The crust comes from the thin layer of cheese they sprinkle along the edge of the dough before it’s put in the super-hot oven.

Other highly recommended places are Lou Malnati’s, Gino’s East and Giordano’s (all have various outlets throughout the city). Try them all on your weekend trip to Chicago. Bring your eating pants!

If you want an expert to show you all the best things to eat in Chicago, check out this foodie tour.

A close-up view of a Chicago-style deep-dish pizza on a white plate, with toppings of olives, mushrooms, and tomatoes, accompanied by a cast iron skillet with more pizza in the background.
Sorry for the blurry image, I was too busy stuffing my face!

Hot dogs at Portillo’s

We also found out that Chicago even has its own style of hot dog. The best place to try it is at Portillo’s (100 W Ontario St). A Chicago hot dog is a beef frankfurter topped with yellow mustard, chopped onions, sweet pickle relish, tomato, a dill pickle, pickled sport peppers and celery salt. And it was SO tasty. Apparently, no ketchup allowed!

If you do go to Portillo’s don’t miss the chocolate cake shake – a chocolate milkshake literally full of chunks of chocolate cake. Seriously decadent.

A classic Chicago-style hot dog on a poppy seed bun with mustard, relish, onions, tomatoes, a pickle spear, sport peppers, and a dash of celery salt, wrapped in paper.
Tucking into a Portillo’s hot dog

The Publican

The Publican’s (837 Fulton St) menu is farmhouse-inspired and diners sit at huge communal tables. We sat at the bar right outside the door to the kitchen, so we saw all the food coming out. The atmosphere is noisy and jovial and perfect for a night out with a group of friends.

avec Restaurant

Next on the list was avec Restaurant (615 W Randolph St). The menu is tapas-style Mediterranean dishes, so we tried a number of different items. Another restaurant with communal-style seating, we ended up sharing a table with a lovely Mexican couple and their young daughter, and got to try even more plates after they realised they’d over-ordered.

There’s a new avec Restaurant in River North that’s bigger than the one we went to in West Loop.

The Duck Inn

The Duck Inn (2701 S Eleanor St) is located in a less touristy part of the city, but it’s worth the detour for the killer brunch. You’re definitely not coming here for a healthy start to the day – you’re coming to sample delicious food in a cosy environment.

A gourmet sandwich featuring crispy fried chicken and red cabbage slaw between two flaky biscuits, skewered with a toothpick, presented on a dark, textured plate. You can fit in a lot of meals in 48 hours in Chicago!

Au Cheval

The last meal of our weekend in Chicago was burgers at Au Cheval (800 W Randolph St). No reservations, so get here early and get your name in the queue. Even on a Monday at 11.30am the place was packed. The burgers here are totally worth the calories, as are the delicious cocktails.

A cheeseburger with multiple patties, cheese, pickles, and onions, served on a glossy brioche bun with a steak knife stabbed through the center for support, next to a pickle spear. Au Cheval's burgers are one of the most famous things to eat in Chicago.

Where to stay in Chicago

There are a tonne of places for a weekend in Chicago, with hotels to suit every budget.


  • A new-ish hotel in Chicago, the five-star Langham Hotel has been voted the best hotel in the city. Stunning decor and the classy service that you’d expect of the Langham brand. (330 N Wabash Ave) Check availability and pricing online with Booking.com or Expedia | Read guest reviews
  • The boutique hotel Thompson Chicago is located in the heart of downtown. (21 E Bellevue Pl) Check availability and pricing online with Booking.com or Expedia | Read guest reviews


  • During our weekend in Chicago, we stayed at theWit. It’s stylish, close to both Millennium Park and the river, and the staff organised cupcakes and glasses of bubbles for my husband’s birthday. What more could we ask for? (201 N State St) Check availability and pricing online with Booking.com or Expedia | Read guest reviews


  • The Hotel Versey is comfortable with fun pops of colours and prints adorning the walls of the rooms. (644 W Diversey Pkwy) Check availability and pricing online with Booking.com | Read guest reviews

When to visit Chicago

Chicago is a USA bucket list destination that you can visit year-round – but the seasons can be extreme.

The best times to visit Chicago are April to May and between September and October. During those months, it’s warm and the summer crowds have calmed down somewhat. We visited Chicago in late October and had perfect blue skies for most of the visit.

Summer is peak season and prices are higher.

Winter months are bitterly cold and the river often freezes over entirely.

How to get around Chicago

Chicago is an incredibly walkable city and we clocked up many miles during our weekend in Chicago. Downtown has an easy-to-navigate grid system, where Madison Street divides the city north and south, while State Street divides it east and west.

If venturing further, Uber is always a great choice. We did most of our travelling in Ubers and the drivers were all super friendly and helpful with sharing their recommendations of things to do in the city.

We caught a few trains as well and it was a straightforward system. The Chicago Transit Authority manages the bus and train network so you can easily use your tickets or passes on both transport options.

Hire a bike through the city’s bike sharing program, Divvy. We saw lots of people riding these bikes along the lake.

For something different, take a water taxiChicago Water Taxi and Shoreline Water Taxi take you to the top Chicago tourist attractions with a sightseeing tour along the way!

Did you find this article helpful? Consider buying me a coffee as a way to say thanks!

Is there anything else you’d do if you only had 48 hours in Chicago? Leave your tips in the comments below!

Related posts

Before you go… you might like these USA city break ideas!


  • Book flights to and around the USA online with Skyscanner. I like this site because it shows me which dates are cheaper.
  • Find a great hotel in the USA. Check prices on Booking.com and Expedia online.
  • Check out the huge range of day tours throughout the USA on GetYourGuide or Viator. There’s something for everyone.
  • A copy of the Lonely Planet guide to the USA will be handy.
  • One thing I always purchase is travel insurance! Travel Insurance Master allows you to compare across multiple policy providers, while SafetyWing is great for long-term travellers and digital nomads.


Save this guide to a weekend in Chicago so you can start planning your city getaway.


I'm a travel junkie who started dreaming about seeing the world from a very young age. I've visited more than 40 countries and have a Master of International Sustainable Tourism Management. A former expat, I've lived in Australia, Papua New Guinea, Argentina and the United States. I share travel resources, tips and stories based on my personal experiences, and my goal is to make travel planning just that bit easier.

18 thoughts on “48 Hours in Chicago: How to Spend a Weekend in the Windy City”

  1. Rebecca, somehow I never came across this post before on your blog and wow — you nailed it! As a local, your post is seriously everything I would recommend or take a friend to while visiting Chicago. I’m so glad I came across your blog before our honeymoon and cant wait to reference it again once we can all travel again!

  2. As someone who’s written about Chicago for 16 years, I can say wholeheartedly that you picked some AMAZING spots! I’m so glad you enjoyed the Windy City. It’s gorgeous, cultured, and a ton of fun. When you come back (because I know you will 🙂 ), be sure to spend more time on the Riverwalk. There are a bunch of places to eat, live music, and even boat docks (besides CAF). Happy to help with more suggestions whenever you return!

    • This comment made me so happy!! Thank you! I am so bummed we didn’t have time to spend on the Riverwalk – it looks like a great place to while away an afternoon with a glass of wine or two. Will definitely reach out when we go back 🙂

    • I was amazed by how quickly the comedians could turn a couple of words into a hilarious improv show, so talented. I hope you get there soon, it’s a great city!

  3. Too often we read about the increasing crime rate in Chicago nowadays, putting aside the fact that it is such a nice city. It’s very refreshing to read your take on the Windy City, Rebecca — a city my best friend also loves for its towering skyscrapers. Oh and that deep-dish pizza looks like something to die for!

    • I know – and I didn’t see any of that while I was in Chicago, but of course it does exist. Such a beautiful city and we found everyone there to be so friendly and laidback.


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