Title: Book the Best Streeterville Hotels with Early Check-in in 2026 from CA $142 | Expedia.ca [Streeterville Travel Guide](https://expedia.ca/Chicago-Streeterville.dx6130109)[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)[Streeterville Car Rentals](https://expedia.ca/Car-Rentals-In-Streeterville.d6130109.Car-Rental-Guide)[Streeterville Vacations](https://expedia.ca/Streeterville.d6130109.Destination-Travel-Guides) ![Navy Pier which includes wild flowers and general coastal views as well as a couple](https://images.trvl-media.com/place/6069215/5854ad1a-e5a8-41d6-a235-77f0217d4701.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6069215/5854ad1a-e5a8-41d6-a235-77f0217d4701.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Streeterville Hotels with Early Check-in Tonight [Jan 31 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6130109&startDate=2026-01-31&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 1 - Feb 2](https://www.expedia.ca/Hotel-Search?regionId=6130109&startDate=2026-02-01&endDate=2026-02-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6130109&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6130109&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Streeterville hotels with express check-in ![Lobby](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/58ac280a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/56c2d84c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 7:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/352e3b39.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/27000000/27000000/26998800/26998765/693d9c34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aloft Chicago Mag Mile [](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information) Downtown Chicago 8.6/10 Excellent (3,065 reviews) "Great location and friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pablo CA $124 CA $145 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/461957e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed with Sofa bed, Corner](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/e4e07af2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/b90174ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/3a5d3e60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Centric Chicago Magnificent Mile [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-Chicago-Magnificent-Mile.h151139.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (1,070 reviews) "Amazing location, excellent service and great pool and hot tub. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tim CA $150 CA $216 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-Chicago-Magnificent-Mile.h151139.Hotel-Information) ![Shopping mall](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/cf0663e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/759e1486.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/f64fa789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/1a16c1e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Millennium Knickerbocker Chicago [](https://www.expedia.ca/Chicago-Hotels-Millennium-Knickerbocker-Chicago.h15087.Hotel-Information) Downtown Chicago 8.6/10 Excellent (2,003 reviews) "Very clean, quiet, and warm reception and service from the staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) tim CA $121 CA $174 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Chicago-Hotels-Millennium-Knickerbocker-Chicago.h15087.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/109a2156.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) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/6ec865cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wade [](https://www.expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) Downtown Chicago 8.4/10 Very good (1,642 reviews) "Lovely room, beautiful hotel, wonderful staff, ideal location to navy pier & Michigan Ave. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Norah CA $148 CA $174 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/20000/15100/15092/bdaa578c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/20000/15100/15092/8bb6d772.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/20000/15100/15092/840ce013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Multiple Beds (The Drake Residence) | Living area](https://images.trvl-media.com/lodging/1000000/20000/15100/15092/w3840h2549x0y4-79cac6c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Drake [](https://www.expedia.ca/Chicago-Hotels-The-Drake.h15092.Hotel-Information) Downtown Chicago 8.8/10 Excellent (1,383 reviews) "Always a great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tracey CA $161 CA $189 total includes taxes & fees Feb 7 - Feb 8 [](https://www.expedia.ca/Chicago-Hotels-The-Drake.h15092.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/580000/571400/571328/357f9e12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/580000/571400/571328/7163999b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/580000/571400/571328/2ee04c4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/580000/571400/571328/5a6cccaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites Chicago Downtown / Magnificent Mile [](https://www.expedia.ca/Chicago-Hotels-Fairfield-Inn-Suites-Chicago-Downtown-Magnificent-Mile.h571328.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (1,001 reviews) "The room was cozy and breakfast was very good and the staff were very kind and welcoming." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ibrahim CA $121 CA $142 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Chicago-Hotels-Fairfield-Inn-Suites-Chicago-Downtown-Magnificent-Mile.h571328.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/10700/10607/97bbd3be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Refrigerator & Microwave | Living area](https://images.trvl-media.com/lodging/1000000/20000/10700/10607/4eb87158.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/20000/10700/10607/d83a4f86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Refrigerator & Microwave | View from room](https://images.trvl-media.com/lodging/1000000/20000/10700/10607/3bc31c7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Chicago Downtown/Magnificent Mile [](https://www.expedia.ca/Chicago-Hotels-Hampton-Inn-Chicago-DowntownMagnificent-Mile.h10607.Hotel-Information) Downtown Chicago 8.0/10 Very good (1,394 reviews) "Great hotel,, like so much" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ilham CA $128 CA $151 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Chicago-Hotels-Hampton-Inn-Chicago-DowntownMagnificent-Mile.h10607.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/14000000/13500000/13492100/13492029/af819b4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/14000000/13500000/13492100/13492029/fe620a82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/14000000/13500000/13492100/13492029/a8c570d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![LCD TV, pay movies](https://images.trvl-media.com/lodging/14000000/13500000/13492100/13492029/98f027a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Inn Chicago Downtown Magnificent Mile [](https://www.expedia.ca/Chicago-Hotels-Residence-Inn-Chicago-Downtown-Magnificent-Mile.h13492029.Hotel-Information) Downtown Chicago 9.6/10 Exceptional (452 reviews) "Cozy, Friendly, Good place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donghyeon CA $189 CA $222 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Chicago-Hotels-Residence-Inn-Chicago-Downtown-Magnificent-Mile.h13492029.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18100/18035/efd0770d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/20000/18100/18035/1487003b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/20000/18100/18035/558fea26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/18100/18035/d310d8dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chicago Marriott Downtown Magnificent Mile [](https://www.expedia.ca/Chicago-Hotels-Chicago-Marriott-Downtown-Magnificent-Mile.h18035.Hotel-Information) Downtown Chicago 8.8/10 Excellent (1,001 reviews) "Beautiful hotel! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Annette CA $237 CA $326 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Chicago-Hotels-Chicago-Marriott-Downtown-Magnificent-Mile.h18035.Hotel-Information) ![Suite, 2 Bedrooms, Terrace (Lakeshore) | Lake view](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/e5b56b9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/7da48e89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/1e19db6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/ee956af2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Seasons Hotel Chicago [](https://www.expedia.ca/Chicago-Hotels-Four-Seasons-Hotel-Chicago.h25748.Hotel-Information) Downtown Chicago 9.4/10 Exceptional (999 reviews) "Beautiful hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sean CA $572 CA $671 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Chicago-Hotels-Four-Seasons-Hotel-Chicago.h25748.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=2026-02-15&endDate=2026-02-16®ionId=6130109&adults=2&property_amenities_group_explore=express_checkin&sort=RECOMMENDED&openPlayBack=true) ## Top Streeterville Hotel Reviews ![Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical](https://images.trvl-media.com/lodging/1000000/30000/26000/25929/4e2c019f_y.jpg) ### Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical 10/10 Excellent "Room was clean, staff very friendly! " [](https://expedia.ca/Chicago-Hotels-Sonesta-ES-Suites-Chicago-Downtown.h25929.Hotel-Information) ![The Whitehall Hotel, BW Premier Collection](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg) ### The Whitehall Hotel, BW Premier Collection 10/10 Excellent "Whether for leisure, business or staycation, " [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![The Wade](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61_y.jpg) ### The Wade 10/10 Excellent "Lovely room, beautiful hotel, wonderful staff, ideal location to navy pier & Michigan Ave. " [](https://expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown Magnificent Mile](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/da498d1e_y.jpg) ### Embassy Suites by Hilton Chicago Downtown Magnificent Mile 10/10 Excellent "Don’t listen to any reviews saying the place wasn’t clean, was old, etc. We were fully satisfied with our stay. Room was huge and modern, hotel was clean and staff were friendly. " [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown-Magnificent-Mile.h570329.Hotel-Information) ![Hyatt Centric Chicago Magnificent Mile](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/w3837h2249x3y0-2724cf53_y.jpg) ### Hyatt Centric Chicago Magnificent Mile 10/10 Excellent "Very nice" [](https://expedia.ca/Chicago-Hotels-Hyatt-Centric-Chicago-Magnificent-Mile.h151139.Hotel-Information) ![DoubleTree by Hilton Chicago - Magnificent Mile](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e_y.jpg) ### DoubleTree by Hilton Chicago - Magnificent Mile 10/10 Excellent "2nd time at hotel and will come again. " [](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![Warwick Allerton - Chicago](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg) ### Warwick Allerton - Chicago 10/10 Excellent "Great place" [](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) ![Courtyard by Marriott Chicago Magnificent Mile](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/529d8be8_y.jpg) ### Courtyard by Marriott Chicago Magnificent Mile 10/10 Excellent "Everything was nice, from the atmosphere to the room. I enjoyed my stay " [](https://expedia.ca/Chicago-Hotels-Courtyard-By-Marriott-Chicago-Magnificent-Mile.h982517.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "Excellent " [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [3 Star Hotels in Magnificent Mile ](https://www.expedia.ca/3Star-Magnificent-Mile-Chicago-Hotels.s30-n800025-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Magnificent Mile ](https://www.expedia.ca/4Star-Magnificent-Mile-Chicago-Hotels.s40-n800025-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Magnificent Mile ](https://www.expedia.ca/5Star-Magnificent-Mile-Chicago-Hotels.s50-n800025-0.Travel-Guide-Filter-Hotels) - [Business Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Business-Hotel.0-0-d178248-tBusinessHotel.Travel-Guide-Filter-Hotels) - 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