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Hand-picked deals by our pirate team

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Hand-picked deals by our pirate team
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TravelPirates

Hand-picked deals by our pirate team

Get inspired!

Hand-picked deals by our pirate team
Chicago, Chicago river, Illinois
Vacations

3-Night Squad Trip to the Windy City—In the 200s w/ Flights

Breeze Into Chicago & Visit The Bean Without Breaking the Bank 🌬️🍕🫘

From $209

Published by
Katrina Kerr·2/1/2025
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Need a getaway with more than just your bestie? Round up the crew and snag this incredible deal—3 nights in Chicago with flights included starting at just $209!

Chicago has something for everyone, from world-class museums and iconic landmarks to an unbeatable food scene and endless entertainment options. Whether you're into deep-dish pizza, jazz clubs, or stunning city views, this trip has you covered.

Stay at Freehand Chicago (4/5 on TripAdvisor), just two blocks from Michigan Avenue in the heart of River North. With flexible room options—including bunk beds—it’s perfect for the whole gang!

Start your mornings with a pick-me-up at Café Integral, or kick off the night with a cocktail at Broken Shaker before exploring all that Chicago has to offer.

Highlights

Family Friendly
Flights included
Free Extras
Free Wifi
Great Food
Great for Couples
Great for Groups
Great for Solo Travel
Gym & Fitness
See All Highlights

Departure

  • Charlotte
  • Atlanta
  • Dallas
  • New York
  • Miami
  • New Orleans
  • Los Angeles
  • Denver
  • Washington
  • Phoenix
  • Las Vegas
  • Boston
  • Philadelphia
  • San Francisco

Destination

  • Chicago

Additional Information

*All of our deals are available at the time of publishing, but prices are subject to fluctuations and changes at any time.

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City TripsClubbingFoodieFree ExtrasInstagrammableMini BreakSpring BreakSpringUnder 500WellnessWinter
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