Black FridayDealsBuying guidesBrandsStoresFlight dealsHotel dealsResearchTermsPrivacydeal.ai apps
Black Friday 2026:WalmartBest BuyTargetTVsLaptopsHeadphonesAppleGamingVacuumsKitchenToysSmartwatchesTabletsFurnitureMattresses

© Deal.ai Inc.

BrowseBrowse deal.ai
Deal.ai › Hotels › Chicago

Chicago Hotel Deals

Hotels in Chicago that Google Hotels prices at least 25% under their usual rate, up to 60% less, found by Deal.ai's AI agents and re-checked through the day. Each is priced for a 2-night stay on the dates shown; open one to see it and book with the hotel.

Ask our shopping agent

It checks today's price at every store, compares the alternatives and answers in about a minute.

Enter to send, Shift+Enter for a new line

  • LIVN Millennium Park Downtown Chicago−60%
    Hotels·Google Hotels·4.1

    Chicago at your doorstep, Millennium Park out the window

    Chicago · Fri, Nov 13 – Sun, Nov 15

    $195.00per night$487.50 usual rate
    Deal score 10.0 · Unreal
  • The Tremont Chicago Hotel−55%
    Hotels·Google Hotels·3.8

    Chicago's Magnificent Mile at your doorstep

    Chicago · Fri, Nov 20 – Sun, Nov 22 · 3-star hotel

    $159.00per night$353.33 usual rate
    Deal score 9.2 · Unreal
  • LIVN Millennium Park Downtown Chicago−52%
    Hotels·Google Hotels·4.1

    Wake up over Millennium Park with the Chicago skyline out your window

    Chicago · Fri, Nov 20 – Sun, Nov 22

    $238.00per night$495.83 usual rate
    Deal score 8.7 · Steal
  • McCormick Place Guest House−49%
    Hotels·Google Hotels·3.8

    Sleep steps from McCormick Place

    Chicago · Fri, Nov 13 – Sun, Nov 15 · 3-star hotel

    $127.00per night$249.02 usual rate
    Deal score 8.2 · Steal

Hotel deals in other cities

  • Las Vegas
  • New York
  • Miami Beach
  • Orlando
  • Los Angeles
  • San Francisco
  • New Orleans
  • Nashville
  • San Diego
  • Cancun
  • Paris
  • London
  • Rome
  • Barcelona
  • Tokyo
  • Lisbon
  • Amsterdam

Flight deals

  • Atlanta
  • Dallas
  • Denver
  • Chicago
  • Los Angeles
  • New York
  • Las Vegas
  • Orlando
  • Miami
  • Fort Lauderdale
  • Charlotte
  • Seattle
  • Phoenix
  • San Francisco
  • San Jose
  • Houston

Questions and answers

How are these Chicago hotel deals found?
Deal.ai's agents search Google Hotels for Chicago through the day and keep the stays Google itself marks as well under their usual rate.
What dates are these prices for?
A 2-night stay, checking in on the dates each deal shows. Rates change by date, so check your own dates with the hotel or ask the agent.
How often are they updated?
Several times a day; a stay whose rate goes back up comes off this page.
  • Hyatt House Chicago / West Loop-Fulton Market−47%
    Hotels·Google Hotels·4.3

    Sleep steps from Chicago's best food and nightlife

    Chicago · Fri, Nov 13 – Sun, Nov 15 · 3-star hotel

    $217.00per night$409.43 usual rate
    Deal score 7.8 · Steal
  • Loews Chicago Hotel−46%
    Hotels·Google Hotels·4.6

    Loews Chicago stay a short stroll from the Magnificent Mile

    Chicago · Fri, Nov 20 – Sun, Nov 22 · 4-star hotel

    $326.00per night$603.70 usual rate
    Deal score 8.2 · Steal
  • Hampton Inn Chicago Downtown/Magnificent Mile−44%
    Hotels·Google Hotels·3.9

    Sleep steps from the Magnificent Mile without the Magnificent bill

    Chicago · Fri, Nov 13 – Sun, Nov 15 · 3-star hotel

    $189.00per night$337.50 usual rate
    Deal score 7.3 · Great deal
  • Freehand Chicago−42%
    Hotels·Google Hotels·3.9

    Freehand Chicago: design hostel vibes in River North

    Chicago · Fri, Nov 20 – Sun, Nov 22 · 4-star hotel

    $88.00per night$151.72 usual rate
    Deal score 7.0 · Great deal
  • The Tremont Chicago Hotel−41%
    Hotels·Google Hotels·3.8

    Chicago weekends just got a whole lot easier

    Chicago · Fri, Nov 13 – Sun, Nov 15 · 3-star hotel

    $159.00per night$269.49 usual rate
    Deal score 6.8 · Great deal
  • Hilton Chicago−41%
    Hotels·Google Hotels·4.3

    Sleep steps from the lake in a grande dame Hilton

    Chicago · Fri, Nov 13 – Sun, Nov 15 · 4-star hotel

    $186.00per night$315.25 usual rate
    Deal score 6.8 · Great deal
  • Freehand Chicago−34%
    Hotels·Google Hotels·3.9

    Sleep in style in Chicago without the downtown splurge

    Chicago · Fri, Nov 13 – Sun, Nov 15 · 4-star hotel

    $94.00per night$142.42 usual rate
    Deal score 4.7 · Good deal
  • Bali
  • Punta Cana
  • Austin
  • Scottsdale
  • Washington DC
  • Boston
  • Minneapolis
  • Detroit
  • Philadelphia
  • Salt Lake City
  • Baltimore
  • Washington
  • San Diego
  • Tampa
  • Nashville
  • Austin
  • Honolulu
  • Portland
  • St. Louis
  • Raleigh
  • Sacramento
  • New Orleans
  • San Antonio