Chicago in a weekend

Are you looking to visit Chicago in a weekend? If so, you’re in luck! Chicago is an incredibly vibrant, exciting, and rather clean city with a sprinkle of midwest charm. I would normally recommend visiting for longer than a weekend, but you can still have an incredible trip with just a weekend! If you need more reasons to visit, check out my 20 reasons you need to visit Chicago blog I wrote back in the day.

I’ve been to Chicago many times over the years and every time I go I seem to fall more and more in love with the city. Now that my sister lives here I get to visit even more and find it so fun to view everything through a locals eye! Here’s my curated list of everything you should do in Chicago in a weekend. I hope you have as much fun as I do every time I visit!

Getting to Chicago

Flights go in and out of Chicago from all over the world every single day and since Chicago is so central, it’s fairly easy to get to and from most places in the USA. The largest airport in Chicago is Chicago O’Hare and the smaller airport is Chicago Midway. Chicago Midway is on the South side of Chicago and is only 8 miles from the Loop (downtown). If you can find a cheap flight to Chicago Midway I’d recommend that airport since it’s closer to the city. 

getting to ChicagoIf you fly into Chicago O’Hare and are going to take an uber/lyft/taxi into the city just be prepared to potentially be in the car for a little over an hour (the traffic can be brutal no matter when you go).

Where to Stay in Chicago over the Weekend

There are so many options for places to stay in Chicago, but I recommend staying in the heart of the city so you can walk everywhere! Staying in the Loop is a great option if you want to be central. However, you can’t really go wrong if you stick to most of the downtown areas like River North, Streeterville, Gold Coast. Here are some of my favorite hotels for your weeekend in Chicago.

Claridge House - Chicago

Claridge House – Chicago

Budget Accommodation: 

The Publishing House Bnb – This is a super cute B&B located in the West Loop, but away from all the hustle and bustle of the downtown Loop. This is a great place to relax after a long day of touristing around Chicago! See current prices. 

Freehand Chicago This is a hostel style hotel that’s good for groups. If you want to get a room together or for a room for just two people, this is a great option. It’s also great for a girls trip or bachelorette weekend and the decor is super cute! See current prices.

Mid-Range Accommodation: 

Claridge House – I stayed here with my family on a girls trip and we LOVED this hotel. Plus, it was in a great neighborhood and is right across the street from Restoration Hardware’s famous cafe! I would 100% stay here again. See current prices.

The W – City Center – I stayed in this hotel a few years ago and loved it. I felt like I was in a swanky, big city hotel and it was so fun. The location is great and the rooms are cool! See current prices. 

St. Jane Hotel – This hotel is in a great, central location. The tower rooms are really amazing while the other rooms are just okay, but this is a good mid-price hotel depending on the weekend you’re visiting. See current prices. 

I haven’t done an Airbnb in Chicago, but that’s another great option if you’re looking for more of an apartment vibe and want your own space. Get $40 your first Airbnb booking here.

chicago riverwalk

Getting Around Chicago 

Chicago has a pretty good train and bus system that I would recommend for getting around. We took a lot of ubers/lyfts since they were readily available as well. If you stay downtown, walking will be super easy. Just remember that Chicago does have large city blocks and sometimes things may appear closer than they really are!

What to Do For a Weekend in Chicago 

Go to Second City, a Broadway show, or visit a smaller non-equity theatre

I highly, highly recommend going to Second City if you can. It’s a super well known improv comedy show in Chicago and is where Tina Fey and Steve Carell got their start. It’s SO freaking hilarious, I died laughing. I also saw Hamilton in Chicago and always see great Broadway shows playing. If you’re in the mood for an off-Broadway show or want to visit a Storefront theatre, I recommend visiting a show done by The Neighborhood (my sisters theatre company) or the NeoFuturists!

Hamilton in Chicago

Go to Millenium Park to see the Bean

I’m assuming this is already on your list, but it’s a MUST! You have to get a picture of the Bean (actually called Cloud Gate) and see the other fun art in the park. Fun fact: you can get a great view of the Bean from above if you go to Cindy’s rooftop for a drink! 

The Bean in Chicago

Chicago’s First Lady Boat Architecture Tour

This is always a highlight for me and I’ve done it twice! All the girls in my family did it together and we LOVED it. I recommend this Chicago First Lady Boat Tour company. They actually have local volunteers do the tour and they are sooo good! They actually do it for free and don't ask for tips. Definitely try booking in advance if you can. Oh, and if you go anytime outside of summer be sure to bring layers because it's about 10 degrees colder on the water and the winds are strong. 

architecture tour in Chicago

Wrigley Field for a Cubs Game

Okay, I honestly haven’t been to a Cubs game yet and it makes me slightly sad, but I’m hoping to next time! I do know from my close friends and family that these games are well worth the hype and pre-gaming before a weekend game down in Wrigleyville is super fun. 

Visit the Art Institute of Chicago

I don’t usually go to art institutes when I’m in other cities, but this one I’ve been to 3x cause it’s so good!  I can honestly spend hours here checking out the modern exhibits or tiny house exhibit. This is also a great rainy day activity if you happen to be there on a rainy day.

art institute of chicago

Shop the Magnificent Mile 

I’m not a huge shopper, but this shopping area is pretty wild and obviously long (hence the mile). Basically if you don’t live in a big city, you’ll find every shop you could ever want right here on the mile!

Take a walk along the water with views of the city, make it over to Navy Pier, or go on a river walk

The craziest thing about Chicago is that it’s right on a lake and you can literally go to the beach in the city which is so cool to me. I recommend taking a walk out by the water for the views of the city or heading over to Navy Pier. Navy Pier is super touristy though so if you'd rather walk along the river, that's a fun option too!

Chicago river walk

Get a picture in front of the famous Chicago sign at the Chicago Theatre

You’ll most likely see this sign if you’re walking around downtown, but it’s always fun to get a pic in front of the theatre!

chicago theatre sign

Take a stroll through Andersonville

This is the neighborhood my sister and her boyfriend live in and it’s so cute and up and coming! It’s a bit north of downtown and is adorable and well worth the visit. Check out Martha Mae’s Art Shop (it’s the most beautiful shop ever), La Colombe for a coffee, Middle Eastern Bakery for lunch, Little Bad Wolf for a cocktail and dinner and HopLeaf for a beer. There are fun shops (Brimfield) and thrift shops all around to keep you occupied as well!

andersonville obama mural

Food & Drinks in Chicago

There are so many amazing places to eat and drink in Chicago that it’s hard to narrow everything down, but here are some of my favorite spots that you shouldn’t miss.

Cindy’s Rooftop

If you go anywhere to eat/drink in Chicago it should be here. The reason I say this is because it has everything in one. It’s got Chicago’s stylish city scene, mixed with a rooftop patio looking over Millenium Park (the Bean!), and has wonderful brunch, dinner and cocktails. Plus, it’s in the Chicago Athletic Association building which you should go walk around as well. If you go to the 2nd floor you can check out the lobby and grab a coffee in their speakeasy-esque library! This whole building is a VIBE! Just remember it can get crowded so go early or make a reservation. 

Restoration Hardware’s 3 Arts Club Cafe

Please do yourself a favor and go get brunch or lunch at Restoration Hardware. Yes, it may seem weird to eat in a store, but it’s wonderful. Pricey, but beautiful. You may want to get a reservation, but we walked right at 9am and all 6 of us were seated. After your meal you can walk around the Restoration Hardware store and then walk through the neighborhood to see all the amazing houses. The original PlayBoy Mansion is right nearby also! If you stay at the Claridge House you’ll be right down the street from Restoration Hardware!

restoration hardware brunch

Revival Food Hall

Talk about vibes! This place brings the vibes. With the lighting, decor and overall food selections, you really can’t go wrong here. Think trendy food court with all of Chicago's best food and that's Revival. This is great if you have a group that can’t make decisions because everyone can get their own thing!

Hampton Social

This place has come on the map mainly because of its instagrammable ‘Rose All Day’ sign, but is super cute, trendy and has great food and bevvies!

Deep Dish Pizza

Chicagoans fight over the best place to get deep dish, so you might not want to take it from me. However, the best places I’ve been in Chicago are Gino’s East and Lou Malnatti’s and you kind of need to get a deep dish while you're in Chi-town.

lou malnattis

Untitled Supper Club or Three Dots and a Dash

Both of these have speakeasy vibes and take some sleuthing to find, but both have great cocktails and will guarantee a fun time. three dots and a dash


This is a Chicago staple and is open super late! Go here and get a goblet of beer and literally anything on their menu. I’m all about the Chicago dog and I get one whenever I visit. Don’t forget to get a side of cheese to dip your fries in!


Chicago Cut

Need a good midwest Chicago steak in your life? Go to Chicago Cut. It’s pricey but so good. 


This is another food hall located in a multi-story mall but has all different types of Latin cuisine. The decor was super fun and the food was so yummy!

Go out on the town

 If you’re trying to party or go out to the bars, I recommend Hubbard Street, River North, Old Town, Wicker Park, or Wrigleyville.

The best thing about Chicago is that there are so many places to eat and drink and you really can’t go wrong! These are just some of the staples and favorite spots I’ve been to, but am always on the lookout for more!

I hope you have a wonderful time doing Chicago in a weekend! If you happen to be here during St. Patrick’s Day (one of the most popular weekends to visit Chicago), I hope you get to see the river dyed green!

chicago river


Chicago in a Weekend

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