We value your privacy
We use cookies to enhance your browsing experience, serve personalized content, and analyze our traffic. By clicking "Accept All" you accept this and consent that we share this information with third parties and that your data may be processed in the USA. For more information, please read our .
You can adjust your preferences at any time. If you deny, we will use only the essential cookies and unfortunately, you will not receive any personalized content. To deny, .
🌬Unwind In The Windy City With An 🧑🎨Artsy Weekend!
Get a 4⭐️ weekend stay and roundtrip flights for as low as $220!
From $220
Chicago is having a big year - hot chefs and big songs are bringing this classic American city back into the limelight!
We found you a great vacation package that gets you to the Windy City and into a 4-star room at the 21c Museum Hotel Chicago (4.5/5 on TripAdvisor) for under $500 from most departure cities! This hotel is conveniently located in the Loop and features exciting art exhibitions and a delightful bar!
These weekend vacations also include roundtrip, often nonstop flights with American, Spirit and Frontier!
Book now for a weekend at Wrigley, munching on deep dish and enjoying the summer sun on the Lake!
Highlights
Departure
- Philadelphia
- Denver
- Dallas
- Miami
- Phoenix
- Seattle
- Washington
- Los Angeles
- New York City
- Orlando
- San Francisco
- Boston
Destination
- Chicago
Details
Here are some of the dates and departure airports we found for you, but there are many more available.
Here's the best flight we found...
Additional Information
All of our deals are available at the time of publishing, but prices are subject to fluctuate and change at any time.
Download Our App
The easiest way to see all our content first.
Gallery
Tags