See tonight’s deals in Chicago

Chicago Hotel Deals & Discounts

Second City - First-Rate Deals

  • 3 star average$150
  • 4 star average$229
  • 5 star average$324

Great deals in Chicago

All 38 deals
Four Seasons Hotel Chicago
Four Seasons Hotel Chicago
  • 5 stars
Loved by guests
Outstanding 4.7 / 5
Prices fromfrom
$395
Stay 3 nights and get the 3rd night free
Travel between Mon 18 June 2012-Wed 1 April 2020
Fairmont Chicago at Millennium Park
Save up to 33%
Fairmont Chicago at Millennium Park
  • 4.5 stars
Excellent 4.3 / 5
Prices fromfrom
$249
$224
Save 33%
Travel between Thu 7 December 2017-Sun 30 December 2018
Swissotel - Chicago
Save up to 30%
Swissotel - Chicago
  • 4.5 stars
Excellent 4.4 / 5
Prices fromfrom
$189
Save 30%
Travel between Thu 12 April 2018-Sun 31 March 2019
Central Loop Hotel
Save up to 30%
Central Loop Hotel
  • 4 stars
Excellent 4.2 / 5
Prices fromfrom
$139
Save 30%
Travel between Fri 3 November 2017-Tue 4 September 2018
River Hotel
Save up to 30%
River Hotel
  • 4 stars
Excellent 4.2 / 5
Prices fromfrom
$130
Save 30%
Travel between Fri 3 November 2017-Tue 4 September 2018
The Willows Hotel
Save up to 30%
The Willows Hotel
  • 3 stars
Excellent 4.1 / 5
Prices fromfrom
$130
$110
Save 30%
Travel between Wed 17 January 2018-Thu 31 January 2019
Warwick Allerton - Chicago
Save up to 28%
Warwick Allerton - Chicago
  • 4 stars
Excellent 4.1 / 5
Prices fromfrom
$106
Save 28%
Travel between Wed 12 April 2017-Sun 31 March 2019
House 5863- Chicago's Premier Bed and Breakfast
Save up to 25%
House 5863- Chicago's Premier Bed and Breakfast
  • 3.5 stars
Loved by guests
Excellent 4.5 / 5
Prices fromfrom
$85
Save 25%
Travel between Thu 1 March-Mon 16 July 2018
Ambassador Chicago
Save up to 25%
Ambassador Chicago
  • 4 stars
Excellent 4.1 / 5
Prices fromfrom
$159
Save 25%
Travel between Fri 2 March-Mon 31 December 2018
The Whitehall Hotel
Save up to 25%
The Whitehall Hotel
  • 4 stars
Excellent 4.1 / 5
Prices fromfrom
$105
Book early and save 25%
Travel between Sat 21 April-Mon 31 December 2018
Inn of Chicago
Save up to 25%
Inn of Chicago
  • 3 stars
Good 3.4 / 5
Prices fromfrom
$139
$111
Book early and save 25%
Travel between Sun 8 April 2018-Thu 28 February 2019
Dewitt Hotel and Suites
Save up to 24%
Dewitt Hotel and Suites
  • 3 stars
Good 3.8 / 5
Prices fromfrom
$109
Save 24%
Travel between Tue 17 April-Fri 30 November 2018
All 38 deals

Best deals on Chicago hotels

The best deals for Chicago hotels are here at Hotels.com. Find out how much you can save! Enter your travel dates and check on our hotel deals online. Our hotel price discounts and offers for hotels in Chicago vary from 10-50% off- This is how much you can save. Find a hotel that is convenient to you and see how much you are saving on your booking. Our hotel rates and savings vary depending on you booking dates. Try a few dates to travel to Chicago and compare your savings. Our booking engine shows you the best hotel deals in Chicago so you are always saving. Make a Chicago hotel booking with Hotels.com to save and sign up to receive special deals and discounts in your email so you can take advantage of exclusive deals and private sales that are not available in the site. And you can also win a Free Night when you stay 10 if you sign up for the Welcome Rewards Program. Whether you are looking for a budget hotel or just searching for hotel deals in Chicago, you will always find the best promotions at Hotels.com. Book with Hotels.com and start saving money on your Chicago hotel stay. Don’t forget to check on our Hotels.com authentic guest reviews before booking a hotel. They help you find top rated hotel in Chicago with featuring deals and special offers. We also provide the TripAdvisor Chicago hotel reviews score and guest reviews from Expedia.

Terms & Conditions

*Sale on participating properties only. Minimum night stay may be required. Offers vary by property. Rooms and prices are subject to availability. Prices do not include taxes and fees and are subject to change without notice. Additional restrictions and blackout dates may apply.