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1. www.kayak.com › packages › chicagoChicago vacation packages from $494 | KAYAK

   www.kayak.com › packages › chicago

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   Search and compare hundred of travel sites at once for vacation packages in Chicago, Illinois. We’re completely free to use - No hidden charges or fees. Filter by free cancellation, free breakfast and more.

2. www.expedia.com › ChicagoChicago Vacation Packages 2024 from $257 | Expedia

   www.expedia.com › Chicago

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   Bundle Chicago flight + hotel & save up to 100% off your flight with Expedia. FREE cancellation on select hotels

3. www.hotwire.com › ChicagoDeals on Chicago Vacation Packages $220 | Hotwire

   www.hotwire.com › Chicago

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   Book a last-minute vacation package with a Hot Rate hotel deal. You could save up to 60% off on your hotel versus booking a listed rate two weeks earlier. How to get the best vacation package deals to Chicago?

4. www.kayak.com › Chicago-Hotels_Last-MinuteLast Minute Hotel Deals in Chicago from $38/day - KAYAK

   www.kayak.com › Chicago-Hotels_Last-Minute

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   Looking for a last minute Chicago hotel? Last minute hotels for tonight from $38/day; tomorrow from $38/day; this weekend from $33/day. Compare last minute prices of 3,051 Chicago hotels - KAYAK.

5. www.travelocity.com › lp › dealsChicago Getaways - Last Minute Hotel & Flight Deals Chicago IL...

   www.travelocity.com › lp › deals

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   Planning your next Chicago Getaway? Find Last Minute Hotels & the Best Flight Deals to Chicago, backed by our Price Match Guarantee. Don't Delay, Book Today!

6. www.lastminute.com › holidays › us_united-statesChicago Holidays 2024 | Cheap Flight + Hotel Packages |...

   www.lastminute.com › holidays › us_united-states

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   Looking for holidays to Chicago? Find great deals on Chicago holidays at lastminute.com. Book your flight and hotel together and save.

7. www.travelocity.com › ChicagoChicago Vacation Packages 2024/2025 from $256 | Travelocity

   www.travelocity.com › Chicago

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   Looking for exceptional deals on Chicago , IL trips and vacation packages? Save when you bundle your flight and hotel. Book your trip today!