Hand-picked deals by our pirate team
Get inspired!
Hand-picked deals by our pirate team
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, .
👨🍳 Say "Yes, Chef!" To A Weekend In Chicago!
Slice 15+% off these fantastic weekend vacays to the Windy City!
From $383
Fly to Chicago for a weekend tasting all that this great American city has to offer!
Enjoy the Hyatt Place Downtown/The Loop (4.5/5 on TripAdvisor) spacious rooms, prime location and comfy digs before diving into the Windy City's vibrant music and foodie scene. Explore Millennium Park, marvel at the Art Institute, and shop the Magnificent Mile. Or enjoy local staples like deep-dish, Chicago hot dogs and some of the country's top restaurants!
These weekend vacations also include roundtrip - often nonstop - flights with Frontier, Spirit and others!
Highlights
Departure
- New Orleans
- Philadelphia
- Dallas
- Portland
- Boston
- Atlanta
- Washington
- Las Vegas
- New York City
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 cheapest deal 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
Report a legal concern