Blog, U.S. Travel

A Long Weekend in Chicago

Chicago, Illinois has been on my want-to-visit list for a while. In the spirit of just go, I went last month! I signed up for the Chicago Spring Half Marathon and tacked on a few extra days to explore the city.

Here are some things that I did and loved and my suggestions for a long weekend in Chicago.

Live like a local. Chicago has lots of little neighborhoods, each with their own character. I stayed in a cute AirBNB apartment in Wicker Park, a quiet, but accessible neighborhood with its own strip of restaurants, bars, and shops on Milwaukee Avenue. It was a great home base for everything I wanted to do and see while there.

Snap a selfie with the bean. And a bunch of other tourists. I went straight from the race!

Cruise the Chicago River. Chicago’s First Lady is a 90-minute history and architecture tour through the city. It was my favorite part!

Marvel at Lake Michigan. The Lakefront Trail is a beautiful place for a run (the race course was on the trail!), walk, or bike ride. In warmer weather, I would have also spent some time relaxing at North Avenue Beach or Oak Street Beach.

Laugh at a Second City show. Second City was one of my must-sees. It’s the comedy troupe that Tina Fey and Cecily Strong got their start in. There are a few theaters and shows around town, I saw The Winner of Our Discontent at the Chicago Mainstage.

Catch a Cubs game at Wrigley Field. Iconic ballpark, great views, fun event – and they even handed out hats at the game I attended!


Stroll through the Lincoln Park Zoo. Close to the Lakefront Trail and on the way to Wrigleyville, the zoo is small but has some fun exhibits and my favorite part was walking out one of the exits and finding this amazing view of the city.


Grab a drink with a view at Signature Lounge. Instead of standing in line to catch the city view from Chicago 360 or the Skydeck, head to the Signature Lounge for a slightly overpriced cocktail, but a great view of the city and lake.


Eat great food! Some of my favorites were:

Get around cheaply and easily. You don’t need a car in Chicago, and it’s actually a hindrance if you try to drive into downtown. Keep it simple by taking the CTA Blue Line from O’Hare into the city. It’s a 30-45 minute trip for $5.

Bike Chicago with Divvy. Bike riding is just fun! It’s a great way to cover some ground but slow down to really see things. Divvy is a bike sharing service that offers you as many 15-minute rides as you want within 24 hours for $10. There are many stations around the city and 15 minutes is plenty of time to get to your next stop.

Walk and Uber. Chicago is a walkable city (when the weather is nice) or if time was of the essence, most Ubers were usually less than $10.

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