A Weekend Away: Chicago, IL


Going to Chicago for the weekend is a great option for my Midwestern friends. It’s a pretty easy drive, and even if you prefer to fly, there are plenty of direct flights that go there. Although it’s the Midwest’s biggest city, Chicago is relatively small compared to N.Y.C. or L.A., making it a simpler visit than its larger U.S. counterparts.

We were in Chicago for a grand total of 12 hours. We flew in at 7 a.m. on a Saturday morning and left for the airport at 7 p.m. that same evening. Here’s how we conquered the Windy City:


John Hancock Center

The John Hancock Center’s observatory (now called “360 CHICAGO”) is the best way to see the expansive city of Chicago. It is located way up on the 94th floor and has 360-dregree views that overlook Chicago’s skyscrapers. It costs a pretty penny, but I loved the chance to see the city from a different perspective.

Wrigley Field

The historic Wrigley Field, home of the Chicago Cubs, is located right in the city. Accessible by the ‘L,’ Wrigley Field is a must-visit for all. We bought tickets off a street scalper in the third inning for a few bucks and ended up seeing rookie Kris Bryant’s MLB debut.

Navy Pier

I mostly go to Navy Pier for the sweets – I never miss out on the opportunity to eat ice cream or a funnel cake by the water. Regardless of personal reasons, Navy Pier is a family-friendly place with great food, a Ferris wheel, fireworks and more. The definition of an all-around good time.

A view of the lake from 360 CHICAGO (observatory) in the John Hancock Center.


The ‘L’

The ‘L’ is a subway/train line that transfers passengers around the city and into the suburbs. It goes to both Midway and O’Hare airports which makes the ‘L’ a convenient way to get into the city.


Portillo’s Hot Dogs

If you love hotdogs on a summer day, then head to Portillo’s. (I’ve only ever met one person that doesn’t like hotdogs – shoutout to you. I won’t shame you and say your name in front of everyone.) Although Portillo’s menu is limited, the experience is one-of-a-kind. It is fast-paced, so be prepared to order when you go up to the counter… unless you enjoy getting impatient looks from the busy workers. We ate at Portillo’s for lunch, and our meal was extremely cheap, considering we were in the middle of Chicago.

Lou Malnati’s

If there is one thing in life my husband and I will always agree on, it’s pizza. In the nutrition pyramid, pizza is our bottom layer. Thin-crust pizza. Thick-crust pizza. Pizza for breakfast. Pizza for dinner.

When we went to Chicago, we knew we wanted to eat deep-dish pizza for dinner. We chose to go to Lou Malnati’s, and it was an excellent choice. Upon entering the restaurant it seemed too fancy, but surprisingly we were both able to eat personal-sized, deep-dish pizzas for a reasonable amount.

Inside Portillo’s Hot Dogs

What do you like to do in Chicago?

The Wayfaring Woman

**Click below to learn what this series is about and view other weekend destinations.
Part 1
Part 2
Part 3
Part 4
Part 5

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