Title: Chicago Vacation Packages & Trips 2025/2026 from CA $493 | Expedia.ca [Chicago Travel Guide](https://expedia.ca/Chicago.dx178248)[Hotels in Chicago](https://expedia.ca/Chicago-Hotels.d178248.Travel-Guide-Hotels)[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)[Chicago Car Rentals](https://expedia.ca/Car-Rentals-In-Chicago.d178248.Car-Rental-Guide) ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chicago Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence ### Better together Save up to CA $1,096 when you book a flight and hotel together\* ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package ### Rest easy Plan, book, and manage your trip all in one place ## Top Chicago Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Grand Vacations Club Chicago Magnificent Mile Downtown Chicago CA $493 per person Nov 24 - Nov 26 found 11 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (291 reviews) Food price was high but everything was fine Reviewed on Oct 4, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-24/2025-11-26/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=1qy9L2f9MnB3Zlaf3cNbvuLWLKJArzhmfznXw9Qg8P_Iyg_wY4dsJ2I3rzOKLyw3) ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago CA $706 per person Dec 29 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) The bed was extremly comfortable Staff was very attentive. Highly recommend Reviewed on Oct 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=QpLfFRqLVDnisD62S_OWRvGucY9sT0vsc-mbrfGmaJD60fTjKcyoYc26N2UVKOtS) ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago CA $1,300 per person Dec 29 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) Awesome room amazing tub even better service Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&dealMarker=QpLfFRqLVDnisD62S_OWRiIj5R-oi1GV9v65jDP6DpGKB0MnvMIYg2eu51kC_N_s) ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### theWit Chicago, a Hilton Hotel Downtown Chicago CA $645 per person Dec 29 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,004 reviews) Clean room, friendly staff, great location and within walking distance from all shops! Reviewed on Oct 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&dealMarker=QpLfFRqLVDnisD62S_OWRqL1Cvhldn8BYwWawZlzEL_uu4zfItAFs2bdLqVizoxu) ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago CA $803 per person Dec 29 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,222 reviews) Perfect location and atmosphere Reviewed on Oct 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&dealMarker=QpLfFRqLVDnisD62S_OWRnId1qwA-98ixJvgTs-M2BiK3uyLUeW3R1OnY0Bf-ANi) ## Where to stay in Chicago Find the best Chicago areas and neighborhoods for the activities you enjoy most. [Learn more about Chicago](https://expedia.ca/Chicago.dx178248) ![Downtown Chicago showing a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332072-Downtown-Chicago.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Downtown Chicago 5 out of top 10 points of interest in this area The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art. [Find hotel + flight trips in Downtown Chicago](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Mountain%20View,%20California,%20United%20States%20of%20America&Destination=Downtown%20Chicago&DestID=6350699&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Magnificent Mile - River North](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24577-Magnificent-Mile.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Magnificent Mile Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service. [Find hotel + flight trips in Magnificent Mile](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Mountain%20View,%20California,%20United%20States%20of%20America&Destination=Magnificent%20Mile&DestID=800025&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![The Loop - Downtown featuring a river or creek](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/192000/192013-The-Loop-Downtown.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### The Loop Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago. [Find hotel + flight trips in The Loop](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Mountain%20View,%20California,%20United%20States%20of%20America&Destination=The%20Loop&DestID=800024&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543369-chicago.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### River North Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building. [Find hotel + flight trips in River North](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Mountain%20View,%20California,%20United%20States%20of%20America&Destination=River%20North&DestID=6350695&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Chicago which includes modern architecture and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54398-Chicago.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Lincoln Park Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads. [Find hotel + flight trips in Lincoln Park](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Mountain%20View,%20California,%20United%20States%20of%20America&Destination=Lincoln%20Park&DestID=6059328&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ### Things to do in Chicago Chicago is perfect for family-friendly, outdoor, and city-themed vacations. Visitors can explore a variety of attractions, from shopping districts to entertainment venues, and enjoy educational experiences. Key highlights include the iconic Ferris wheel, along with options for cheap vacation packages and golf vacations. Plan your trip to experience the vibrant culture and diverse activities that Chicago has to offer. **Shopping** In Chicago, [Woodfield Mall](https://www.expedia.ca/Woodfield-Mall.d6064089.Vacation-Attraction) offers a vibrant shopping experience with entertainment and family-friendly amenities. For unique gifts, visit [LEGOLAND® Discovery Center](https://www.expedia.ca/LEGOLAND-Discovery-Center.d6169680.Vacation-Attraction). [Chicago Place Mall](https://www.expedia.ca/Chicago-Place-Mall.d6199336.Vacation-Attraction) caters to shoppers with a mix of businesses and city vibes, perfect for finding souvenirs and more. **Recreation** At [Wrigley Field](https://www.expedia.ca/Wrigley-Field.d6034754.Vacation-Attraction), soak in the vibrant sports atmosphere while cheering for the Cubs. Experience the charm of the [Chicago Theatre](https://www.expedia.ca/Chicago-Theatre.d6064049.Vacation-Attraction) with its captivating performances, perfect for a romantic night out. For music lovers, the [Aragon Ballroom](https://www.expedia.ca/Aragon-Ballroom.d553248621563220754.Vacation-Attraction) offers exhilarating concerts in a stunning historic venue. **Adventure** Experience the thrills at [Great Wolf Lodge Water Park](https://www.expedia.ca/Great-Wolf-Lodge-Water-Park.d726364538049507328.Vacation-Attraction), where you can splash down water slides and enjoy family-friendly attractions. For arcade fun, head to [Galloping Ghost](https://www.expedia.ca/Galloping-Ghost.d553248621532658619.Vacation-Attraction) for classic games and excitement. If you seek nature, hike along [Salt Creek Trail](https://www.expedia.ca/Salt-Creek-Trail.d553248621532658620.Vacation-Attraction) for stunning scenery and outdoor adventure. **Nightlife** Chicago's nightlife is vibrant and diverse. Visit [Dave & Buster's](https://www.expedia.ca/Dave-Busters.d553248621532658508.Vacation-Attraction) for a fun atmosphere with drinks and games. For a more intimate experience, [Kingston Mines](https://www.expedia.ca/Kingston-Mines.d6322633.Vacation-Attraction) offers live music and a romantic vibe. [Blues on Halstead](https://www.expedia.ca/Blues-On-Halstead.d6322643.Vacation-Attraction) is perfect for enjoying soulful tunes in a lively setting with a city backdrop. *\*Distances are measured in a straight line; actual driving distances may vary depending on the route.* ### Find the best attractions in Chicago Chicago is a fantastic destination for families and outdoor enthusiasts, offering a vibrant mix of urban parks, beautiful beaches, and renowned colleges. Explore downtown Chicago and discover top attractions that cater to a variety of interests, from cultural experiences to family-friendly activities. Whether you're seeking a city adventure or a relaxing day outdoors, this city has something for everyone to enjoy. - **[Navy Pier:](https://www.expedia.ca/Navy-Pier.d6069215.Vacation-Attraction)** Experience the vibrant atmosphere of Navy Pier, where you can enjoy stunning views of Lake Michigan, dine at waterfront restaurants, and explore unique shops. The pier often hosts events and entertainment, making it a lively destination for all ages. - **[Michigan Avenue:](https://www.expedia.ca/Michigan-Avenue.d6156167.Vacation-Attraction)** Known as the Magnificent Mile, Michigan Avenue is a bustling street lined with high-end shops, historic buildings, and cultural attractions. Stroll along this iconic avenue to soak in the dynamic city vibe and discover local art and architecture. - **[McCormick Place:](https://www.expedia.ca/McCormick-Place.d6069191.Vacation-Attraction)** As the largest convention centre in North America, McCormick Place hosts major events, trade shows, and conferences. The modern facilities and diverse offerings make it a hub for business and innovation in Chicago. ### Best time to go to Chicago The best time to visit Chicago is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | --- | --- | --- | --- | --- | --- | | January | 25.7°F (-3.5°C) | Light Rain | Mostly | Slightly Low | Slightly Low | | February | 27.0°F (-2.8°C) | Light Rain | Mostly | Slightly Low | Slightly Low | | March | 37.0°F (2.8°C) | Light Rain | Mostly | Average | Average | | April | 46.0°F (7.8°C) | Light Rain | Mostly Sunny | Slightly Low | Average | | May | 57.0°F (13.9°C) | Light Rain | Mostly Sunny | Average | Average | | June | 67.3°F (19.6°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | July | 73.4°F (23.0°C) | Light Rain | Mostly Sunny | Slightly High | Average | | August | 73.0°F (22.8°C) | Light Rain | Mostly Sunny | Slightly High | Average | | September | 67.1°F (19.5°C) | Light Rain | Mostly Sunny | Average | Slightly High | | October | 54.9°F (12.7°C) | Light Rain | Mostly Sunny | Average | Slightly High | | November | 42.3°F (5.7°C) | Light Rain | Mostly Sunny | Average | Average | | December | 33.1°F (0.6°C) | Light Rain | Mostly | Average | Slightly Low | ### Tips to save on your trip to Chicago - Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Chicago. - Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Chicago. - Use the *Price per traveler* filter on Expedia to find a package deal that suits your budget. - Check the *VIP Access properties* filter to discover outstanding hotels with added member perks at select properties. ## Ready to book your vacation to Chicago? Choose your dates ## Chicago Hotel Deals ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Congress Plaza Hotel 520 South Michigan Avenue, Chicago, IL Fully refundableReserve now, pay when you stay CA $179 CA $210 total Nov 2 - Nov 3 includes taxes & fees 7.8/10 Good! (9,342 reviews) "We did not use laundry service, and the front desk staff did not mention any availbale services" Reviewed on Oct 7, 2025 [](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=178248) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Embassy Suites by Hilton Chicago Downtown River North 600 N State St, Chicago, IL Fully refundableReserve now, pay when you stay CA $214 CA $251 total Nov 9 - Nov 10 includes taxes & fees 8.4/10 Very Good! (5,072 reviews) "The onsite parking is worth the money compared to other lots. Walk where you can. The Embassy is in the perfect location for a lot of attractions." Reviewed on Oct 9, 2025 [](https://expedia.ca/Hotel-Search?startDate=09%2F11%2F2025&endDate=10%2F11%2F2025&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=178248) ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago/Magnificent Mile Suites 198 E Delaware Pl, Chicago, IL Fully refundableReserve now, pay when you stay CA $201 CA $236 total Nov 9 - Nov 10 includes taxes & fees 8.8/10 Excellent! (3,034 reviews) "Awesome hotel. Super nice staff!" Reviewed on Oct 6, 2025 [](https://expedia.ca/Hotel-Search?startDate=09%2F11%2F2025&endDate=10%2F11%2F2025&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true®ionId=178248) [See all 5,380 properties in Chicago](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=11%2F10%2F2025&endDate=12%2F10%2F2025®ionId=178248) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Discover the most popular places to visit in Chicago ![Wrigley Field featuring central business district, a city and a sporting event](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/35000/35620-Wrigley-Field.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wrigley Field Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium. [](https://expedia.ca/Wrigley-Field-Lakeview.d6034754.Vacation-Attraction) ![Magnificent Mile - River North which includes signage, a city and night scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23728-Magnificent-Mile.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Michigan Avenue You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants. [](https://expedia.ca/Michigan-Avenue-Downtown-Chicago.d6156167.Vacation-Attraction) ![Navy Pier](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54738-Navy-Pier-Chicago.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Navy Pier A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district. [](https://expedia.ca/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction) ### What to do in Chicago ![River tour boat in Chicago](https://mediaim.expedia.com/localexpert/170432/2ab44ef1-1211-4f4f-9436-ce9a14d4241f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Architecture River Tour CA $67 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/architecture-river-tour.a170432.activity-details) ![Relax and enjoy the view](https://mediaim.expedia.com/localexpert/46106377/6686561e-a3aa-4cbf-9e71-f553bde2fa06.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago Architecture Center River Cruise aboard First Lady CA $77 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/chicago-architecture-center-river-cruise-aboard-first-lady.a46106377.activity-details) ![Color Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/1b6e1be3-a6ba-4b3d-8e57-4d0336c3fd23.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Color Factory Chicago Ticket CA $47 per adult **94%** of travellers recommend [](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.activity-details) [See all activities in Chicago](https://expedia.ca/things-to-do/search?rid=178248) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars ### Lodging - [3 Star Hotels in The Loop](https://www.expedia.ca/3Star-The-Loop-Chicago-Hotels.s30-n800024-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in The Loop](https://www.expedia.ca/4Star-The-Loop-Chicago-Hotels.s40-n800024-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in The Loop](https://www.expedia.ca/5Star-The-Loop-Chicago-Hotels.s50-n800024-0.Travel-Guide-Filter-Hotels) - [Hotels near Adams-Wabash Station](https://www.expedia.ca/Adams-Wabash-Station-Hotels.d6210258.Travel-Guide-Hotels) - [Houseboats in Adams-Wabash Station](https://www.expedia.ca/Adams-Wabash-Station-Houseboats.d6210258-aaHouseboats.Travel-Guide-Accommodation) - [Hotels near Art Institute of Chicago](https://www.expedia.ca/Art-Institute-Of-Chicago-Hotels.0-l6064021-0.Travel-Guide-Filter-Hotels) - [Hotels near CIBC Theatre](https://www.expedia.ca/CIBC-Theatre-Hotels.0-l553248621563220853-0.Travel-Guide-Filter-Hotels) - [Hotels near Chagall's Four Seasons](https://www.expedia.ca/Chagalls-Four-Seasons-Hotels.0-l553248621533116569-0.Travel-Guide-Filter-Hotels) - [Hotels near Chase Tower](https://www.expedia.ca/Chase-Tower-Hotels.0-l553248621555594882-0.Travel-Guide-Filter-Hotels) - [Hotels near Chicago Temple](https://www.expedia.ca/Chicago-Temple-Hotels.0-l553248621561883126-0.Travel-Guide-Filter-Hotels) - [Hotels near Chicago Theatre](https://www.expedia.ca/Chicago-Theatre-Hotels.0-l6064049-0.Travel-Guide-Filter-Hotels) - [Downtown Chicago Hotels](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels.0-n6350699-0.Travel-Guide-Filter-Hotels) - [Aparthotels in Madison-Wabash Station](https://www.expedia.ca/Madison-Wabash-Station-Apart-Hotels.d6210251-aaApartHotels.Travel-Guide-Accommodation) - [Hotels near Madison-Wabash Station](https://www.expedia.ca/Madison-Wabash-Station-Hotels.d6210251.Travel-Guide-Hotels) - [Inns in Madison-Wabash Station](https://www.expedia.ca/Madison-Wabash-Station-Inns.d6210251-aaInns.Travel-Guide-Accommodation) - [Magnificent Mile Hotels](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels.0-n800025-0.Travel-Guide-Filter-Hotels) - [Hotels near Millennium Park](https://www.expedia.ca/Millennium-Park-Hotels.0-l6069201-0.Travel-Guide-Filter-Hotels) - [Hotels near Monroe Station](https://www.expedia.ca/Monroe-Station-Hotels.d6189309.Travel-Guide-Hotels) - [Houseboats in Monroe Station](https://www.expedia.ca/Monroe-Station-Houseboats.d6210064-aaHouseboats.Travel-Guide-Accommodation) - [Hotels near Richard J. Daley Center](https://www.expedia.ca/Richard-J-Daley-Center-Hotels.0-l6175173-0.Travel-Guide-Filter-Hotels) - [Hotels near State Street](https://www.expedia.ca/State-Street-Hotels.0-l6175182-0.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Adults-Only-Resorts.0-n800024-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-All-Inclusive-Hotel.0-n800024-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Beach-Hotel.0-n800024-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Best Western Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Best-Western.0-n800024-0--bBestWestern.Travel-Guide-Filter-Hotels) - [Boutique Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Boutique-Hotel.0-n800024-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Cheap-Hotels.0-n800024-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Destination Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Destination-Hotels.0-n800024-0--bDestinationHotels.Travel-Guide-Filter-Hotels) - [Fairmont Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Fairmont.0-n800024-0--bFairmont.Travel-Guide-Filter-Hotels) - [Family Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Family-Hotel.0-n800024-0-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Golf Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Golf-Hotel.0-n800024-0-tGolfHotel.Travel-Guide-Filter-Hotels) - [Hilton Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hilton-Hotels.0-n800024-0--bHiltonHotels.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Honeymoon-Hotels.0-n800024-0-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotel-With-Pool.0-n800024-0-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with Bar in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Bar.0-n800024-0-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Hotels with Free Airport Shuttle in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Free-Airport-Shuttle.0-n800024-0-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Free-Breakfast.0-n800024-0-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Free-Parking.0-n800024-0-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Hot-Tubs.0-n800024-0-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Indoor-Pool.0-n800024-0-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Hotels with Tennis Courts in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Tennis-Courts.0-n800024-0-tHotelswithTennisCourts.Travel-Guide-Filter-Hotels) - [Kimpton Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Kimpton-Hotels.0-n800024-0--bKimptonHotels.Travel-Guide-Filter-Hotels) - [Lake Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Lake-Hotels.0-n800024-0-tLakeHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Luxury-Hotel.0-n800024-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Marriott Hotels & Resorts in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Marriott-Hotels-Resorts.0-n800024-0--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Oceanfront-Hotels.0-n800024-0-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Pet-Friendly-Hotel.0-n800024-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Romantic-Hotel.0-n800024-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Shopping Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Shopping-Hotel.0-n800024-0-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Spa-Hotel.0-n800024-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [The Loop Hotels](https://www.expedia.ca/The-Loop-Chicago-Hotels.0-n800024-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Theatre District](https://www.expedia.ca/Theatre-District-Chicago-Hotels-Cheap-Hotels.0-n651190586167894016-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Theatre District](https://www.expedia.ca/Theatre-District-Chicago-Hotels-Luxury-Hotel.0-n651190586167894016-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Theatre District Hotels](https://www.expedia.ca/Theatre-District-Chicago-Hotels.0-n651190586167894016-0.Travel-Guide-Filter-Hotels) ### Flights - [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago) ### Packages - [900 North Michigan Shops](https://www.expedia.ca/900-North-Michigan-Shops-Downtown-Chicago.d6199347.Vacation-Attraction) - [Ann and Robert H. Lurie Children's Hospital](https://www.expedia.ca/Ann-And-Robert-H-Lurie-Childrens-Hospital-Downtown-Chicago.d553248624898453771.Vacation-Attraction) - [Aon Center](https://www.expedia.ca/Aon-Center-Downtown-Chicago.d6064015.Vacation-Attraction) - [Art Institute of Chicago](https://www.expedia.ca/Art-Institute-Of-Chicago-Downtown-Chicago.d6064021.Vacation-Attraction) - [Buckingham Fountain](https://www.expedia.ca/Buckingham-Fountain-Downtown-Chicago.d6064027.Vacation-Attraction) - [Cibc Theatre](https://www.expedia.ca/CIBC-Theatre-Downtown-Chicago.d553248621563220853.Vacation-Attraction) - [Carbide and Carbon Building](https://www.expedia.ca/Carbide-And-Carbon-Building-Downtown-Chicago.d553248621555594910.Vacation-Attraction) - [Central Chicago Vacations](https://www.expedia.ca/Central-Chicago.d553248635976475413.Destination-Travel-Guides) - [Visit Downtown Chicago](https://www.expedia.ca/Chicago-Downtown-Chicago.dx6350699) - [Chicago Harbor Lighthouse](https://www.expedia.ca/Chicago-Harbor-Lighthouse-Chicago.d6064039.Vacation-Attraction) - [Chicago Riverwalk](https://www.expedia.ca/Chicago-Riverwalk-Downtown-Chicago.d553248621533116610.Vacation-Attraction) - [Visit The Loop](https://www.expedia.ca/Chicago-The-Loop.dx800024) - [Chicago Theatre](https://www.expedia.ca/Chicago-Theatre-Downtown-Chicago.d6064049.Vacation-Attraction) - [Cloud Gate](https://www.expedia.ca/Cloud-Gate-Downtown-Chicago.d6182888.Vacation-Attraction) - [Downtown Chicago Vacations](https://www.expedia.ca/Downtown-Chicago.d6350699.Destination-Travel-Guides) - [Grant Park](https://www.expedia.ca/Grant-Park-Downtown-Chicago.d507389.Vacation-Attraction) - [House of Blues Chicago](https://www.expedia.ca/House-Of-Blues-Chicago-Downtown-Chicago.d6227753.Vacation-Attraction) - [International Museum of Surgical Science](https://www.expedia.ca/International-Museum-Of-Surgical-Science-Downtown-Chicago.d6065139.Vacation-Attraction) - [John Hancock Center](https://www.expedia.ca/John-Hancock-Center-Downtown-Chicago.d6065131.Vacation-Attraction) - [Magnificent Mile Vacations](https://www.expedia.ca/Magnificent-Mile.d800025.Destination-Travel-Guides) - [Marina City](https://www.expedia.ca/Marina-City-Downtown-Chicago.d553248621533116577.Vacation-Attraction) - [Michigan Avenue](https://www.expedia.ca/Michigan-Avenue-Downtown-Chicago.d6156167.Vacation-Attraction) - [Millennium Park](https://www.expedia.ca/Millennium-Park-Downtown-Chicago.d6069201.Vacation-Attraction) - [Navy Pier](https://www.expedia.ca/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction) - [Richard J. Daley Center](https://www.expedia.ca/Richard-J-Daley-Center-Downtown-Chicago.d6175173.Vacation-Attraction) - [Shops at North Bridge](https://www.expedia.ca/Shops-At-North-Bridge-Downtown-Chicago.d6227764.Vacation-Attraction) - [South Loop Vacations](https://www.expedia.ca/South-Loop.d6130108.Destination-Travel-Guides) - [The East Bank Club](https://www.expedia.ca/The-East-Bank-Club-Downtown-Chicago.d553248621555594881.Vacation-Attraction) - [The Loop Vacations](https://www.expedia.ca/The-Loop.d800024.Destination-Travel-Guides) - [Water Tower Place](https://www.expedia.ca/Water-Tower-Place-Downtown-Chicago.d6064087.Vacation-Attraction) - [Willis Tower](https://www.expedia.ca/Willis-Tower-Downtown-Chicago.d6064069.Vacation-Attraction) - [Wrigley Building](https://www.expedia.ca/Wrigley-Building-Downtown-Chicago.d6064091.Vacation-Attraction) ### Cars - [Alamo Rent A Car Rental Cars in The Loop](https://www.expedia.ca/Alamo-Rent-A-Car-Car-Rentals-In-The-Loop.d800024-c6.Car-Rental-Guide-Suppliers) - [Avis Rental Cars in The Loop](https://www.expedia.ca/Avis-Car-Rentals-In-The-Loop.d800024-c41.Car-Rental-Guide-Suppliers) - [Car rentals near Richard J. Daley Center](https://www.expedia.ca/Car-Rentals-In-Richard-J-Daley-Center.d6175173.Car-Rental-Guide) - [Car rentals near The Loop](https://www.expedia.ca/Car-Rentals-In-The-Loop.d800024.Car-Rental-Guide) - [Dollar Rent A Car Rental Cars in The Loop](https://www.expedia.ca/Dollar-Rent-A-Car-Car-Rentals-In-The-Loop.d800024-c43.Car-Rental-Guide-Suppliers) - [Enterprise Rental Cars in The Loop](https://www.expedia.ca/Enterprise-Car-Rentals-In-The-Loop.d800024-c15.Car-Rental-Guide-Suppliers) - [Fox Rental Cars Rental Cars in The Loop](https://www.expedia.ca/Fox-Rental-Cars-Car-Rentals-In-The-Loop.d800024-c19.Car-Rental-Guide-Suppliers) - [Oryx Rent A Car Rental Cars in The Loop](https://www.expedia.ca/ORYX-Rent-A-Car-Car-Rentals-In-The-Loop.d800024-c1059.Car-Rental-Guide-Suppliers) - [Payless Rental Cars in The Loop](https://www.expedia.ca/Payless-Car-Rentals-In-The-Loop.d800024-c38.Car-Rental-Guide-Suppliers) - [Rent A Wreck Rental Cars in The Loop](https://www.expedia.ca/Rent-A-Wreck-Car-Rentals-In-The-Loop.d800024-c33.Car-Rental-Guide-Suppliers) - [Routes Rental Cars in The Loop](https://www.expedia.ca/Routes-Car-Rentals-In-The-Loop.d800024-c1101.Car-Rental-Guide-Suppliers) - [Sixt Rental Cars in The Loop](https://www.expedia.ca/Sixt-Car-Rentals-In-The-Loop.d800024-c35.Car-Rental-Guide-Suppliers) - [Thrifty Car Rental Rental Cars in The Loop](https://www.expedia.ca/Thrifty-Car-Rental-Car-Rentals-In-The-Loop.d800024-c45.Car-Rental-Guide-Suppliers) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)