Title: Chicago Vacation Packages & Trips 2025/2026 from CA $647 | 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. ![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 $647 per person Dec 23 - Dec 28 found 5 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,011 reviews) Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel Reviewed on Oct 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-28/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&dealMarker=kDhtpFwUY77IpIJUdgP2xPEFJaq3_6dH-uTIireNiEe0vUWBG3R2pmQ_fQgGMT8i) ![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 $779 per person Dec 29 - Jan 3 found 18 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (303 reviews) I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location. Reviewed on Oct 28, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-03/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=OE4WY_RpwBQtq85g0f3N80AXuDSQcUv0mIQftCfME8K7vzHJtdfdqvfu-VuA5kM2) ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago CA $951 per person Dec 29 - Jan 3 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9/10 Wonderful! (367 reviews) This was our first time at Level Chicago -Old Town. Last year we stayed at Level Chicago - North. Both apartments were really cozy and offered amazing views of the city. Old Town is a great place to stay, the staff overall was professional and polite. The unit was mostly clean, however, some of the towel were stained (seemed like he make up did not come off with bleach). It wasn't to my liking so I did not use them. Also, they knew we were six people but only gave 4 bath towels. I had to request additional. Another thing is that the locks in the bathroom and bedrooms were not working. It was a bit frustrating considering 6 people were sharing one bathroom. The apartment itself is very comfortable, has washer and dryer on site, which is convenient, especially when staying with children. The kitchen was equipped with all the basic needs except a good coffee machine. They have a nespresso machine but I would have rather an actual coffee machine not espresso machine. Safety was key. My family and I felt safe in the building and the area. Parking was not available in the building (the cost is $70 per night) but that wasnt an issue because we found plenty of parking right outside by the meters. Reviewed on Oct 29, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-03/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&dealMarker=OI2HJU0k0dTAxqA1dMUEg46M2d4Chb9OavmJ7ETX51X5ZxTbeJuCJnG0eWdNiJZt) ![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 $824 per person Dec 23 - Dec 28 found 5 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,110 reviews) We loved the Pendry! Reviewed on Oct 27, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-28/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=kDhtpFwUY77IpIJUdgP2xPEFJaq3_6dH-uTIireNiEe6lCpsoxT3UNznMv3JBuIH) ![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago O'Hare Airport O'Hare CA $1,230 per person Jan 18 - Jan 25 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.2/10 Very Good! (2,141 reviews) It needs improvement Reviewed on Oct 28, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-18/2026-01-25/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=8058&paandie=true&dealMarker=yrZ0TBn6Yd3hsppSaARbbzqf6U1ECjzecmnrYvyIbtIGlFz69h6rI2i4578BjKkA) ## 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=Old%20Toronto,%20Toronto,%20Ontario,%20Canada&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=Old%20Toronto,%20Toronto,%20Ontario,%20Canada&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 4.5/5(725 area reviews) 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=Old%20Toronto,%20Toronto,%20Ontario,%20Canada&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=Old%20Toronto,%20Toronto,%20Ontario,%20Canada&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 5/5(20 area reviews) 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=Old%20Toronto,%20Toronto,%20Ontario,%20Canada&Destination=Lincoln%20Park&DestID=6059328&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Ready to book your vacation to Chicago? Choose your dates ## Chicago Hotel Deals ![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 CA $165 CA $193 total Nov 16 - Nov 17 includes taxes & fees 8.4/10 Very Good! (5,162 reviews) We enjoyed our stay, great location for walking around downtown. Reviewed on Oct 27, 2025 [](https://expedia.ca/Hotel-Search?startDate=16%2F11%2F2025&endDate=17%2F11%2F2025&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=178248) ![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 $131 CA $154 total Nov 24 - Nov 25 includes taxes & fees 7.8/10 Good! (9,616 reviews) Check in was easy, things are clean and efficient. The hotel itself needs a facelift in that it smells old and dank and the room itself was strange. A random closet type thing was pushed up agains an adjoining door, the tiles in the bathroom/shower are all crooked and random, it feels like someone ... Reviewed on Oct 28, 2025 [](https://expedia.ca/Hotel-Search?startDate=24%2F11%2F2025&endDate=25%2F11%2F2025&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=178248) ![Freehand Chicago](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Freehand Chicago 19 East Ohio Street, Chicago, IL Fully refundableReserve now, pay when you stay CA $112 CA $156 total Nov 10 - Nov 11 includes taxes & fees 7.8/10 Good! (2,533 reviews) Excellent location close to everything. Room with a double bed was small but had a nice bathroom. Nice and friendly staff. Reviewed on Oct 27, 2025 [](https://expedia.ca/Hotel-Search?startDate=10%2F11%2F2025&endDate=11%2F11%2F2025&selected=9418281&PinnedHotelID=9418281&HadPinnedHotel=true®ionId=178248) [See all 5,463 properties in Chicago](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=30%2F10%2F2025&endDate=31%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 4.5/5(158 reviews) 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 4.5/5(19 reviews) 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 4.5/5(459 reviews) 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 $68 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 $78 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. 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[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. 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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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)