How to Spend a Weekend in Chicago

Only in Chicago for a weekend? Below are the things you should do!

  • See the views from The Signature Room at the 95th.

Head up to the Signature Room bar on the 95th floor of the John Hancock building on Michigan Ave, grab a cocktail and take in some of the best city views. You can also see the views from the Willis Tower observatory deck however you must purchase an admission ticket.IMG-2897 (1)

  • The Green Mill Cocktail Lounge

Located in the Uptown neighborhood, this bar is a hidden gem of Chicago and a definite worthwhile visit. Entering the bar is like stepping into 1940’s Chicago and it is known for having been Al Capone’s local hangout. It contains the original furniture from the 1940’s, weekly jazz bands and a classic Chicago feel. Find out more about the Green Mill here.

  • Catch the Blues Bands at Kingston Mines

A 5 am late night blues venue located in the Lincoln Park neighborhood with some of the best blues bands beginning from 7 pm every evening for the week. To fully experience Chicago Blues and Jazz head here.

  • The Chicago Bean

Also known as the Cloud Gate, this is one of the most iconic sites in Chicago. Be the ultimate tourist and grab a photo in front of bean. The best times to visit are either early in the morning to beat the crowds of tourists that gather around the area later in the day or at night as the reflection of the city lights make for a great photo.


  • Cindy’s Rooftop

Drink some of the best cocktails the city has to offer and take in views from the rooftop patio overlooking Millennium Park. Located on the top floor of the Chicago Athletic Association on Michigan Avenue directly across from the bean. Don’t be afraid to head to the rooftop during winter either as they have fire pits lit!


  • The Drifter

One of the few speakeasy cocktail bars in the city located in the River North Area under the Green Door Tavern. The drifter is particularly special as it is known as one of the first buildings built after the infamous Chicago fire. The cocktail menu is handed to you in the form of a variety of tarot cards and they regularly host burlesque shows.

  • Brunch at River Roast

Chicago goes all out for weekend brunches and River Roast is a great spot to try down by the river walk. This place has great food, cocktails and atmosphere, a live jazz band usual play during the weekend brunch hours so make sure you catch them.

  • The Chicago river walk

After brunch, head for a walk along the river and take in the downtown city views. Along the walk you will find coffee shops and outdoor patio bars.

  • The Architecture Boat Tour

Many tour companies offer architecture boat tours up and down the river. This is a great activity for newbies to the city as the tour guides give an interesting talk about the history of the city and each building along the river.

  • Check out the thrift stores

If you are interested in shopping while in Chicago, definitely check out the quirky thrift stores. Many are located along North Milwaukee Avenue in the Wicker Park neighborhood known for its hipster hangout vibe. Thrift stores on this street include Buffalo Exchange, Crossroads Trading Co., Vintage Underground, Ragstock.

  • The Art Institute

Home of some of the world’s best artwork located in downtown Michigan Avenue. If you are interested in seeing some art exhibitions check out the galleries within the Art Institute. Exhibitions consist of large variety of styles including contemporary and fine art. A must see if you are the artsy type!

  • Bike along the Lakefront

During the warmer months, rent a city bike (“Divvy”) for the day and head onto the lakefront trail. Begin in Lakeview and bike ride to the Shedd Aquarium, you’ll pass some stunning scenes on your way including Millennium park, Buckingham Fountain, Belmont Harbor, and on your final stop at the aquarium take in Chicago’s beautiful skyline.


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  • Girl and The Goat Restaurant

If you are looking for a dinner spot, Girl and the Goat is one of the best restaurant experiences you will find in Chicago. Located in the West Loop, the restaurant specializes in delicious small plates suitable for sharing. Make sure to plan ahead and book well in advance as reservations fill up months ahead of time.

Published by What Lorna Saw Next - Travel

Hello, I'm Lorna! I enjoy backpacking around the world and writing about it. I hope to share my experiences and inspire you with travel recommendations and tips.

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