Title: Book the Best Old Town Chicago Hotels with Early Check-in in 2025 from CA $151 | Expedia.ca [Vacation Rentals in Chicago](https://expedia.ca/Chicago-Vacation-Rentals.d178248.Travel-Guide-VacationRentals)[Flights to Chicago](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Old Town Chicago Car Rentals](https://expedia.ca/Car-Rentals-In-Old-Town-Chicago.d6351828.Car-Rental-Guide)[Old Town Chicago Vacations](https://expedia.ca/Old-Town-Chicago.d6351828.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/11fd6e63e168e646892c8441abd32c9c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by trenton.badillo # Find Hotels with Early Check-in in Old Town Chicago, IL from CA $151 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Old Town Chicago Hotels with Early Check-in Tonight [Nov 4 - Nov 5](https://www.expedia.ca/Hotel-Search?regionId=6351828&startDate=2025-11-04&endDate=2025-11-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 5 - Nov 6](https://www.expedia.ca/Hotel-Search?regionId=6351828&startDate=2025-11-05&endDate=2025-11-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6351828&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6351828&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Old Town Chicago Hotels with Early Check-in ![Cocktail bar](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cocktail bar](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/2aaf07f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/cb4330d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/5132819a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Freehand Chicago Downtown Chicago 8.0/10 Very good (2565) "Location was excellent would stay there again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julio CA $112 CA $157 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/01c93cca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/8318473d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/aaad0ec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palmer House a Hilton Hotel Downtown Chicago 8.4/10 Very good (2068) "Great hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hicham CA $154 CA $216 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/55b627dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/bb272e60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, City View | View from room](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/c06f4b61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast (USD 20.00 per person)](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/8967eebd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### citizenM Chicago Downtown Downtown Chicago 9.2/10 Wonderful (4058) "Clean room, amazing staff, everything was in walking distance. Definitely worth the stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shakeina CA $161 CA $189 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Chicago-Hotels-CitizenM-Chicago-Downtown.h82652306.Hotel-Information) ![1 bedroom, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/943262bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/6d9bcb03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner, brunch served; American cuisine ](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/c042bdff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wade Downtown Chicago 8.4/10 Very good (1413) "Clean room, courteous staff, great location and price!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Theresa CA $156 CA $183 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/4df3bcb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/fb110cc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2695x3y3-e619dd92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency Chicago Downtown Chicago 9.4/10 Exceptional (3393) "Great locations, room was spacious with everything we needed. Hotel has a great breakfast too." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) judith CA $202 CA $279 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/0a522c10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, hypo-allergenic bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/1faa6c2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/9b9a583c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Embassy Suites by Hilton Chicago Downtown River North Downtown Chicago 8.6/10 Excellent (5194) "We enjoyed our stay, great location for walking around downtown. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tami CA $167 CA $196 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Room, 1 King Bed, Corner](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/w3837h2249x3y0-2724cf53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/w3837h2584x3y3-d51aee41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/w3840h2557x0y3-a19ef5e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/w3837h2496x3y3-f9e98aea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Centric Chicago Magnificent Mile Downtown Chicago 9.0/10 Wonderful (1026) "Very clean and staff is very polite and helpful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Irina CA $155 CA $223 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-Chicago-Magnificent-Mile.h151139.Hotel-Information) ![Cocktail bar](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/d755f57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/ada94c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/58ac280a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/50be090a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aloft Chicago Mag Mile Downtown Chicago 8.6/10 Excellent (2881) "Clean room and loved the atmosphere" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Madison CA $128 CA $151 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information) ![Snack bar](https://images.trvl-media.com/lodging/19000000/18060000/18057400/18057374/4844f60a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/19000000/18060000/18057400/18057374/edbd6260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/19000000/18060000/18057400/18057374/0afe31db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18060000/18057400/18057374/w1584h1367x232y0-c5298bdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cambria Hotel Chicago Loop - Theatre District Downtown Chicago 8.8/10 Excellent (1431) "Everything was great!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) TONY CA $157 CA $184 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Chicago-Hotels-Cambria-Hotel-Chicago-Loop-Theatre-District.h18057374.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/f3eb640d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/d2c9858e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Kitchenette (One Room)](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/61142942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/c5202ed7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Club Quarters Hotel Wacker at Michigan, Chicago Downtown Chicago 8.8/10 Excellent (1899) "Great location!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tara CA $137 CA $161 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Club-Quarters-Hotel.h889753.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-19&endDate=2025-11-20®ionId=6351828&adults=2&property_amenities_group_explore=express_checkin&sort=RECOMMENDED&openPlayBack=true) ## Top Old Town Chicago Hotel Reviews ![Hilton Garden Inn Chicago Downtown/Magnificent Mile](//images.trvl-media.com/lodging/1000000/430000/424200/424187/d51caee8_y.jpg) ### Hilton Garden Inn Chicago Downtown/Magnificent Mile 10/10 Excellent "Clean rooms and friendly staff" [](https://expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.Hotel-Information) ![Hotel Felix River North/Magnificent Mile](//images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d_y.jpg) ### Hotel Felix River North/Magnificent Mile 10/10 Excellent "Great" [](https://expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) ![The Allegro Royal Sonesta Hotel Chicago Loop](//images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798_y.jpg) ### The Allegro Royal Sonesta Hotel Chicago Loop 10/10 Excellent "Good service " [](https://expedia.ca/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.Hotel-Information) ![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg) ### Freehand Chicago 10/10 Excellent "Staff interactions were excellent in every aspect. " [](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](//images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "Great staff at the front desk!" [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![The Whitehall Hotel, BW Premier Collection](//images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg) ### The Whitehall Hotel, BW Premier Collection 10/10 Excellent "Best upon arrival and the staff promptly answered any and all concerns" [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![Palmer House a Hilton Hotel](//images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg) ### Palmer House a Hilton Hotel 10/10 Excellent "Room was very clean and well kept" [](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](//images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "Everything was perfect will definitely stay again . " [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Warwick Allerton - Chicago](//images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg) ### Warwick Allerton - Chicago 10/10 Excellent "Room was great. Their service also great. Very nice location. Everything in walking distance. I could see the sears tower and Starbucks Reserve Roastery from my room. Love the place. 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