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⛸ Skate On Over to Chicago for a Spectacular Weekend Vacay!

Save upwards of 20% on these 3-Star weekend getaways to the Windy City this fall and winter - flights and up to 3-night hotel stay included!

From $255

Published by
RobArenella·10/4/2024
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Looking for a weekend getaway packed with city vibes and deep-dish pizza? Chicago's got you! Stroll Navy Pier, snap pics at "The Bean," devour Lou Malnati's, and chill at Lake Michigan!

This package includes a stay at the Home2Suites Chicago, River North (4/5 on TripAdvisor), right downtown in the thick of it! These weekend vacations also include round-trip, often nonstop flights with American, United, Spirit, Frontier, and others!

Highlights

Best time to travel
Excellent Room
Family Friendly
Free Wifi
Great Food
Great for Couples
Highly-Rated
Nonstop Flights
Deluxe Room
See All Highlights

Departure

  • Washington
  • Dallas
  • Houston
  • New York City
  • Phoenix
  • Miami
  • Boston

Destination

  • Chicago

Details

Here are some of the dates and departure airports we found for you, but there are many more available.

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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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Under 500InstagrammableWeekendCity TripsLuxuryStaycationClubbingFoodieGroup HolidayLGBTQ+Last MinuteFallWinter
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