Title: Book the Best ROMANTIC Hotels in Streeterville, Chicago from CA $105 - Streeterville Romantic Getaways | 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) # Find Romantic Hotels in Streeterville, Chicago from CA $105 - ![](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 Romantic Hotels Tonight [Dec 9 - Dec 10](https://www.expedia.ca/Hotel-Search?regionId=6130109&startDate=2025-12-09&endDate=2025-12-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Dec 10 - Dec 11](https://www.expedia.ca/Hotel-Search?regionId=6130109&startDate=2025-12-10&endDate=2025-12-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6130109&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6130109&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Our top choices for Streeterville romantic hotels ![Exterior](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/da498d1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/be69fa71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/2435ca6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/71356b17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Embassy Suites by Hilton Chicago Downtown Magnificent Mile Downtown Chicago 8.2/10 Very good (2750) "Great food clean room friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MARINA CA $116 CA $177 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown-Magnificent-Mile.h570329.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) ![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) ![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 (2956) "Great location, the staff was friendly and the room was very clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Breanna CA $107 CA $125 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/55a8ba7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/a9c979ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake view](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/5d460cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago 9.4/10 Exceptional (2266) "Smooth check in and beautiful hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Monique CA $124 CA $192 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ![Ballroom](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/0030a761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/07c9ead9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/d24507d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Chicago/Magnificent Mile Suites Downtown Chicago 9.0/10 Wonderful (3455) "Great place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) RaShawna CA $146 CA $172 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/eac67ea5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![City view](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/340ea126.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/1000000/20000/15100/15087/2c655ed8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/3912d77d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Millennium Knickerbocker Chicago Downtown Chicago 8.6/10 Excellent (2003) "Great location, clean hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andre CA $123 CA $177 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Chicago-Hotels-Millennium-Knickerbocker-Chicago.h15087.Hotel-Information) ![Breakfast and lunch served](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/529d8be8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and lunch served](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/913433f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/120d903c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/3d8cc8f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Chicago Magnificent Mile Downtown Chicago 9.0/10 Wonderful (1588) "Great location and friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric Lynn CA $135 CA $159 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Chicago-Hotels-Courtyard-By-Marriott-Chicago-Magnificent-Mile.h982517.Hotel-Information) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/4c0ebbe4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/311c65a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake view](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/247d9e5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/e436fe11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sheraton Grand Chicago Riverwalk Downtown Chicago 8.4/10 Very good (1577) "Great room size and location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) tilden CA $206 CA $284 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Chicago-Hotels-Sheraton-Grand-Chicago.h12167.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/50000/50000/49985/2489547a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/50000/50000/49985/63f719c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/50000/50000/49985/17f1a3a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Laundry room](https://images.trvl-media.com/lodging/1000000/50000/50000/49985/3be95933.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Saint Clair- Magnificent Mile Downtown Chicago 8.4/10 Very good (1788) "Great stay in a great area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Giselle CA $88 CA $105 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/Chicago-Hotels-The-St-Clair-Hotel-Magnificent-Mile.h49985.Hotel-Information) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/bc751856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, minibar, in-room safe](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/0347f2d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/949e3d56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Grand Vacations Club Chicago Magnificent Mile Downtown Chicago 9.2/10 Wonderful (325) "Great accommodation, staff really nice, room was spacious and very clean. Perfect location to walk just about anywhere, " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lizbeth CA $207 CA $244 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Grand-Vacations-Chicago-Downtown-Magnificent-Mile.h37641670.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/9833019f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/3f6518d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/a7f85665.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/6000000/5210000/5204900/5204897/661195c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ivy Boutique Hotel Downtown Chicago 8.8/10 Excellent (1038) "Clean room, nice amenities (especially like the rain shower), very centrally located, and friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen CA $134 CA $158 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Chicago-Hotels-Ivy-Boutique-Hotel.h5204897.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=2025-12-24&endDate=2025-12-25®ionId=6130109&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Find out more about Streeterville ### Streeterville attractions for couples Streeterville, a vibrant neighbourhood nestled along Lake Michigan, offers a delightful mix of attractions and activities perfect for the discerning traveller. Begin your adventure at the iconic Navy Pier, where you can enjoy stunning lake views, dine in waterfront restaurants, or take a ride on the Ferris wheel for a bird’s-eye view of the skyline. Just a short stroll away, the Art Institute of Chicago invites art enthusiasts to explore its vast collection, featuring everything from Impressionist masterpieces to contemporary works. Families will love visiting the Shedd Aquarium, home to thousands of aquatic animals, where interactive exhibits make learning fun for children and adults alike. For a taste of the local culinary scene, the bustling Magnificent Mile is just around the corner, an array of gourmet dining options and chic cafés that cater to every palate. After a day of exploration, returning to one of the luxurious hotels in Streeterville is a treat; many feature rooftop pools and lounges that overlook the lake, offering a serene escape amidst the city buzz. With attentive service and amenities designed for comfort, you’ll feel pampered after a long day of adventures. ## Top Streeterville Hotel Reviews ![The Wade](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61_y.jpg) ### The Wade 10/10 Excellent "The room was beautiful. I booked the Premium lake view room. It came with a King bed and a wonderful view. I just wish the room had a microwave but there was a microwave in the grab and go area. " [](https://expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.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 "Loved it" [](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.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 "Perfect location to surrounding area and activities, friendly staff, clean rooms, amazing gym, and delicious food." [](https://expedia.ca/Chicago-Hotels-Hyatt-Centric-Chicago-Magnificent-Mile.h151139.Hotel-Information) ![Millennium Knickerbocker Chicago](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/eac67ea5_y.jpg) ### Millennium Knickerbocker Chicago 10/10 Excellent "We have stayed at this property before and we will continue to do so in the future. The property itself, location, and cost are selling points for us." [](https://expedia.ca/Chicago-Hotels-Millennium-Knickerbocker-Chicago.h15087.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 "The front desk staff are WONDERFUL !!! the rooms are super comfortable!" [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.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 "Kind staff " [](https://expedia.ca/Chicago-Hotels-Courtyard-By-Marriott-Chicago-Magnificent-Mile.h982517.Hotel-Information) ![Silversmith Hotel Chicago Downtown](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4_y.jpg) ### Silversmith Hotel Chicago Downtown 10/10 Excellent "Clean beautifulI room . " [](https://expedia.ca/Chicago-Hotels-Silversmith-Hotel-Chicago-Downtown.h116674.Hotel-Information) ![The Drake](https://images.trvl-media.com/lodging/1000000/20000/15100/15092/w3840h2550x0y3-037e0eb4_y.jpg) ### The Drake 10/10 Excellent "Wonderfully clean room, attentive housekeeping. The entire hotel staff was great. Loved the holiday decor." [](https://expedia.ca/Chicago-Hotels-The-Drake.h15092.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "Very clean room, great breakfast, and very quick response to request for extra blankets." 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