3 Day Itinerary for Chicago in the Fall

If you are wondering what exactly to do on your 3 day trip to Chicago in the Fall, then look no further. Since Chicago has distinct seasons, there are things that I (a local) would recommend depending on which season you visit. A perfect itinerary, in my opinion, strikes a balance between seeing the sights and making reservations in advance where needed, but leaving some downtime to explore and of course shop. And that’s exactly how this itinerary for Chicago is structured.

If you are looking for a quick list of the best Chicago has to offer, check out my Best of Chicago guide. If you are visiting in the Spring and Summer, don’t miss out on that 3 day itinerary which includes the Lakefront.

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Day One | Today is all about Downtown Chicago

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A great place to start the trip is Cindy’s Rooftop (don’t worry, it’s covered in the Fall).  Right on Michigan Avenue, you’ll be able to see Lake Michigan, Millenium Park, and the famous “Chicago Bean”.  Depending on the day of the week you’ll have lunch or brunch (only served on weekends). If you are the type of person that needs sustenance upon waking (I myself need coffee) then grab some coffee and a pastry from whatever local shop is near and then plan to go to Cindy’s for small bites.  The view is not to be missed.

After you’ve seen the city from 13 stories high, take the 5-minute walk to the Art Institue of Chicago. You’ll walk right past the Bean, whose real name is Cloud Gate, and into the second-largest art museum in North America (right behind the Metropolitan Museum of Art in New York).

Related

• Best Hotels in Chicago for every Neighborhood
• Coolest VRBOs in Chicago
• Best Brunch in Chicago

Night

Take some time to go back to the hotel and freshen up before dinner.  Tonight’s spot is Maple & Ash for some of the best food in the city. They are known for their steak, and it’s not to be missed, but everything is amazing. It’s a scene so take the opportunity to get changed and take a Lyft to dinner.  If you get there a little early, you can grab a spot at the bar and have a pre-dinner cocktail, it’s a great spot for people-watching.

After dinner, get back in the Lyft because you are going Uptown to one of my favorite spots in the city, Chicago Magic Lounge. You’ll enter through a faux laundry storefront and enter into a speakeasy-like close-up Magic Show.

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Day Two | Enjoy the city like a local!

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Inside the Restoration Hardware in the Gold Coast is the beautiful 3 Arts Club Cafe and it’s a wonderful spot for brunch in the Fall. With its tall ceilings and tons of glass windows, you get the sense of outside but you’ll be warm and cozy before heading out for the day.

Depending on the weather you can grab a Lyft or go for a nice stroll to Lincoln Park and the Lincoln Park Zoo. It will be about a 20-minute walk to the Zoo, but you’ll hit the park after about 10 minutes from Restoration Hardware. If you aren’t sure how much time you’ll spend it’s still work visiting because it’s totally free! Some of my favorite animal exhibits are the Big Cats (they just came back after some time away for a habitat renovation), the Primates and the Bears (I just realized that was very close to Lions, and Tigers, and Bears, oh my!)

Night

You’ll dine in the Lincoln Park neighborhood and have dinner at Summer House Santa Monica, a West Coast-inspired fresh-fare restaurant. And it’s not too far from this evening’s entertainment…Second City!

If you like comedy then I’m sure some of your favorite comedians have spent some time in The Second City. That’s because it’s a world-renowned improv and comedy club that’s been around for 60 years. They offer a variety of shows on different stages so take a look and I’m sure they’ll have something to appeal to you. I’m partial to the late shows because I prefer them just a little more ‘adult’ but you do you.

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Related: What to do in Milwaukee ( a quick trip from Chicago)

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Day Three | Becoming a fan

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After two substantial brunchs, it’s time to grab a quick coffee and a pastry before you see Chicago from a different view. Depending on where your hotel or VRBO is will probably depend on where you’ll go. Some that I love are Goddess & the Baker, Big Shoulders, and Fairgrounds Cafe.

Next is the Skydeck at the Willis Tower (or as we locals still say, the Sears Tower). At 103 floors, it is the highest observation deck in the United States. If you dare, step into one of the glass boxes overhanging the building as you look down more than 1,300 feet to the ground. It’s a little terrifying, but not something you can do every day.

Then you are off to watch the Chicago Bears play some football at Soldier Field (notice I didn’t say win, I like to be realistic). Since it’s an outdoor stadium with no retractable roof, make sure to check the weather before you come to Chicago so you can pack appropriately.

Night

You can’t visit Chicago for the first time without trying deep-dish pizza. Love it or hate it, you at least need to try it, and that’s what’s for dinner.

Take a Lyft after the game and go to Lou Malnati’s. If you are visiting with enough people to order two pizza’s then you may want to get one deep dish and one thin crust, because it’s pretty good too since it has their signature butter crust. If you are craving some produce in your life the Malnati Salad is so good.

Day drinking always makes me tired (and I typically have a drink at sporting events) so I would call it an early night, knowing tomorrow is a travel day.

Related: Best Hikes Near Chicago

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I hope this has been a good starting point for your Fall itinerary for Chicago.   This is by no means exhaustive and will depend a bit on the weather. If it happens to be a really nice day, I recommend an architectural boat cruise on the Chicago River or perhaps a walk along the lakefront. If you want a snack, hit up Garrett’s Popcorn or Molly’s Cupcake and you won’t be disappointed.  Make sure to check the weather and the sports schedule to see if you need to make any adjustments.  

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