Hand-picked deals by our pirate team
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Hand-picked deals by our pirate team
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💃Magnificent Weekend Vacays On Chicago's Magnificent Mile!
Save up to 30% on these flight + hotel deals and spend less than $500 on a 3⭐️ weekend in Chicago - one of America's most incredible cities!
From $249
Ready for an epic weekend in the Windy City?
Dive into deep-dish pizza at Lou Malnati's, stroll through Millennium Park to see "The Bean," and take in jaw-dropping views from the Willis Tower Skydeck. Don't miss the Navy Pier or a Lake Michigan boat cruise!
Enjoy stays at the Aloft Chicago Mag Mile (4/5 on TripAdvisor) with its polished artsy flair, top of the line amenities and fantastic location on Chicago's Art Deco and central Magnificent Mile.
These weekend vacations also include roundtrip - often nonstop - flights with Frontier, Spirit and others!
Highlights
Departure
- Atlanta
- Houston
- Denver
- Dallas
- Washington
- New York City
- Boston
- Miami
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 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.
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