10 Things to Do During a Weekend in Chicago

Chicago is a big city with a lot of great things to do; it can be overwhelming to decide! To get you started, here are 10 things to do during a weekend in Chicago.

1. GRAB BRUNCH AT INSTAGRAM HOTSPOT – THE HAMPTON SOCIAL

This place is undoubtedly the #1 eatery for bloggers but, even if you’re not looking for that perfect Instagram shot, the food at Hampton Social is absolutely delicious. I tried the fried chicken sandwich, their homemade french fries, and a watermelon salad. The frosé is pretty famously delightful also!

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2. GET PICTURES WITH THE “BEAN” AT MILLENNIUM PARK

A trip to Chicago is not complete until you snap a photo with the bean. Compared to Pittsburgh, Chicago is a highly walkable city, so it’s worthwhile to travel on foot and take in the scenery on your way.

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3. TRY DEEP DISH PIZZA FROM LOU MALNATI’S

The locals tell me that Lou Malnati’s is the best pizza in town, and I was not disappointed! Be sure to show up early to get your name on the list, then order your pizza so it’s ready when you sit down! And if you still have room after all of that deep dish, get the brownie pizza; you won’t be sorry. (Just looking at this makes me hungry for it all over again!)

4. CATCH A SHOW AT SECOND CITY COMEDY CLUB

Second City is the place to be for up-and-coming comedians (notable alumni include Amy Poehler, John Belushi, Chris Farley, Tina Fey, Steve Carell, Rachel Dratch, Stephen Colbert and so many more). After your pizza, head up to the Old Town neighborhood for an evening show. Premium seats are under $50!

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5. SLEEP IN AT THE W LAKESHORE HOTEL

After a late night at Second City, wake up slow at the W Lakeshore hotel. Your hotel room will be stocked with Bliss products to keep you feeling refreshed all weekend long, but if you need an extra boost, try a spa treatment from the in-hotel Bliss Spa.

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 6. SIP COFFEE AT A TRENDY CAFE

Dollop coffee shop is a short ten minute walk from the W Lakeshore hotel. With it’s outdoor seating area, you can relax and read up on the daily happenings before tackling your day.

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(Quick aside: I ended up covered in massive  mosquito bites, so please disregard the dinner they made out of my leg.)

7. STROLL THROUGH NAVY PIER

There are tons of things to do on Navy Pier, but honestly, it’s beautiful just to watch the boats coming and going on the water. If the weather is cooperating, you can come here to catch a boat tour of the city, ride the rides, or go to the theater.

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8. ENJOY HOMEMADE PASTA AT EATALY

Eataly is an indoor Italian market that features fresh meats and seafood, homemade pastas, and delicious desserts. Sit down for a meal at one of the many cafe’s and restaurants inside, and fill up on a freshly made Italian-style meal.

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9.  GET DRINKS AT THE BOARDING HOUSE

The Boarding House is a gorgeous wine bar with amazing food. Enjoy its exposed brick decor while sampling their incredible wine list.

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10. SNAP A PHOTO BEFORE CATCHING YOUR FLIGHT FROM O’HARE

As you head to your gate, don’t forget to pause for a minute to admire the lights in O’Hare‘s underground walkway. The beautiful colors make for a great instagram shot while transporting you to your final destination.

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Have you been to Chicago? What are your favorite things to do? Share your thoughts in the comment section below.

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