Chicago Cheap Holidays

Book a Cheap Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Packages with flights are ATOL protected

Top flight + Cheap hotel deals in Chicago

Price found within the past 48 hours. Click for updated prices.
Freehand Chicago
Hotel Felix River North/Magnificent Mile
River Hotel
Club Quarters Hotel, Central Loop, Chicago
Central Loop Hotel
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4 Night Cheap holidays in Chicago

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
The Whitehall Hotel, BW Premier Collection
River Hotel
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Top Cheap Chicago Hotels

Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave Elk Grove Village IL
  • 22 min drive from Wrigley Field
Stay at this motel in Elk Grove Village. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,949 reviews)
I stayed at this motel for 7 nights, and unfortunately, my experience was very disappointing. The property was extremely dirty, including both the hallways and my room. It didn’t appear that the floors had been properly vacuumed or cleaned. The bathroom was especially concerning, with visible mold ...

Reviewed on 10 May 2026

Motel 6 Elk Grove Village, IL - O'Hare
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
  • 10 min drive from Wrigley Field
Stay at this hotel in Chicago. Enjoy free Wi-Fi, room service and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms in their ...
8/10 Very Good! (2,978 reviews)
The hotel has an amazing vibe and was perfect for walking downtown. Rooms were what you expect from an older building, but the showers were hot and the room was quiet. All in all, a great experience.

Reviewed on 11 May 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
  • 13 min drive from Wrigley Field
Stay at this hotel in Chicago. Enjoy free Wi-Fi, a 24-hour front desk and daily housekeeping. Our guests praise the helpful staff and the clean rooms in their ...
7.4/10 Good! (2,602 reviews)
Very reasonable and convenient

Reviewed on 12 May 2026

Travelodge by Wyndham Downtown Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.