Chicago - An Eventful Weekend Trip

Episode 18 is one is all about Chi-town! The windy city has deep historical roots in American history and it’s all over the architecture and personality of this iconic metropolis. We took a quick weekend trip to Chicago and visited two other states and a national park while on this trip!

You know we can’t take a trip without visiting a national park and getting in some hiking! It was really cool to be sitting along the lake in Indiana Dunes National Park and see Chicago building far across the water. This ide excursion is a must-do on your Chicago weekend trip too if you can make the time for it!

In episode we tell you how to see and do the most in Chicago with just two days. This was all of our first times in the city so these are first time in Chicago things to do recommendations that we did and loved.

Our Chicago travel guide:

• Architecture boat tour in Chicago - a MUST DO
• Millennium Park and “the bean”
• The Chicago riverfront walk
• Navy Pier
• John Hancock 96th Floor Signature Lounge
• Brittanie and Jamal’s first White Claw
• Road trip to Indiana Dunes National Park
• Wrigley Field
• Urkle house from Family matters
• Recommended activities & tours on Viator

Where to Stay:

• theWit Chicago
• River Hotel
• Aloft Chicago

Where to eat in Chicago:

• Lou Malnati's pizza
• Nando’s
• Chicago dog
• Italian beef from Portillos or Al's #1 Italian Beef
• High tea and rooftop bar at London House

Chicago travel tips:

• Renting a car
• A walkable city
• Chicago’s own rideshare service - vida
• Airbnb vs. hotel tips

We've created a downloadable 2 day Chicago Guide and you can add onto this guide by booking additional tours and activities.

Find a great flight deal to Chicago by signing up for Thrifty Traveler Premium and watching the daily flight deals (points & cash) that are emailed directly to you! Use our promo code TS10 to get $10 off your first year subscription.

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