Title: The Loop Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $618 Expedia.ca [The Loop Travel Guide](https://expedia.ca/Chicago-The-Loop.dx800024)[Hotels in The Loop](https://expedia.ca/The-Loop-Chicago-Hotels.0-n800024-0.Travel-Guide-Filter-Hotels)[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)[The Loop Car Rentals](https://expedia.ca/Car-Rentals-In-The-Loop.d800024.Car-Rental-Guide) ![](https://images.trvl-media.com/place/800024/9e323a45-98da-4519-b5ca-71275e70174f.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # The Loop 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 Holiday Package Deals in The Loop Price found within the past 48 hours. Click for updated prices. ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago CA $618 per person Feb 12 - Feb 16 found 22 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Clean room Clean bathroom Friendly staff Reviewed on Jan 1, 2026 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $1,448 per person Mar 24 - Mar 29 found 12 hours ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) It was like a Ritz Carlton like experience without the Ritz Carlton price tag. Reviewed on Dec 31, 2025 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago CA $1,770 per person Mar 24 - Mar 29 found 11 hours ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Emil was a fabulous server at the Lobby Restaurant. I think that’s his name. Tall guy. Becca at front desk also fantastic. The lady who checked us in not so good. Reviewed on Dec 29, 2025 ![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 $978 per person Mar 15 - Mar 19 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Staff was friendly did amazing job with checking us in Reviewed on Dec 25, 2025 ![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 $826 per person Mar 15 - Mar 19 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) Excellent service from staff. Clean rooms and great location Reviewed on Jan 2, 2026 ## Where to stay in The Loop Find the best The Loop areas and neighborhoods for the activities you enjoy most. [Learn more about The Loop](https://expedia.ca/Chicago-The-Loop.dx800024) ![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=Downtown%20Columbus,%20Columbus,%20Ohio,%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=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Magnificent%20Mile&DestID=800025&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=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=River%20North&DestID=6350695&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Chicago which includes rides](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23717-Chicago.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Theatre District While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line). [Find hotel + flight trips in Theatre District](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Theatre%20District&DestID=651190586167894016&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Navy Pier which includes wild flowers and general coastal views as well as a couple](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/297000/297915-Navy-Pier-Chicago.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Streeterville Michigan Avenue and Navy Pier are just a few worthwhile attractions to visit in Streeterville. Travelers also love the fascinating museums, panoramic lake views, and popular shops. [Find hotel + flight trips in Streeterville](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Streeterville&DestID=6130109&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## The Loop Hotel Deals ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Palmer House a Hilton Hotel 17 E Monroe St Chicago IL Fully refundableReserve now, pay when you stay CA $196 CA $264 total Jan 11 - Jan 12 includes taxes & fees 8.4/10 Very Good! (2,203 reviews) Dolores was incredible and our room was gorgeous! Reviewed on Jan 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=11%2F01%2F2026&endDate=12%2F01%2F2026&selected=8079&PinnedHotelID=8079&HadPinnedHotel=true®ionId=800024) ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago 720 S Michigan Ave Chicago IL Fully refundableReserve now, pay when you stay CA $190 CA $263 total Jan 11 - Jan 12 includes taxes & fees 8.4/10 Very Good! (2,461 reviews) Nice pillows Reviewed on Jan 2, 2026 [](https://expedia.ca/Hotel-Search?startDate=11%2F01%2F2026&endDate=12%2F01%2F2026&selected=12570&PinnedHotelID=12570&HadPinnedHotel=true®ionId=800024) ![Club Quarters Hotel Wacker at Michigan, Chicago](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/f3eb640d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Club Quarters Hotel Wacker at Michigan, Chicago 75 E Wacker Dr Chicago IL Fully refundableReserve now, pay when you stay CA $101 CA $118 total Jan 18 - Jan 19 includes taxes & fees 8.6/10 Excellent! (2,023 reviews) Very nice views. Reviewed on Dec 29, 2025 [](https://expedia.ca/Hotel-Search?startDate=18%2F01%2F2026&endDate=19%2F01%2F2026&selected=889753&PinnedHotelID=889753&HadPinnedHotel=true®ionId=800024) [See all 1,240 properties in The Loop](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=03%2F01%2F2026&endDate=04%2F01%2F2026®ionId=800024) 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) ## Frequently asked questions ### How much does a The Loop vacation package cost? ### How do I get a cheap travel package to The Loop? ### Where should I stay in The Loop? ### What are the top hotels in The Loop? ### How far in advance should I book my The Loop vacation? ### What does an Expedia The Loop travel package include? ### Can I choose my airline with a The Loop Expedia vacation package? ### If I'm not able to travel, can I cancel my The Loop vacation package? ### Discover the most popular places to visit in The Loop ![Millennium Park featuring autumn colours, street scenes and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/26000/26436-Millennium-Park.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Millennium Park A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape. [](https://expedia.ca/Millennium-Park-Downtown-Chicago.d6069201.Vacation-Attraction) ![Chicago Riverwalk featuring a river or creek, a bay or harbour and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332109-Chicago-Riverwalk.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago Riverwalk Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped. [](https://expedia.ca/Chicago-Riverwalk-Downtown-Chicago.d553248621533116610.Vacation-Attraction) ![Willis Tower which includes a city, views and central business district](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191767-Chicago.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Willis Tower Visit the Skydeck and gaze down over the Chicago cityscape from a dazzling 1,353 feet above the sidewalk. [](https://expedia.ca/Willis-Tower-Downtown-Chicago.d6064069.Vacation-Attraction) ### Things to do ![Color Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/feac7bb1-c7ea-4b19-8342-818eafa34e83.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Color Factory Chicago Ticket CA $46 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.activity-details) ![Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting](https://mediaim.expedia.com/localexpert/4973725/0b36f3b1-b375-4fa2-8cfd-1a9815dcdcdc.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting CA $49 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/medieval-torture-museum-ticket-with-audio-guide-and-ghost-hunting.a4973725.activity-details) ![Chicago's Navy Pier Centennial Wheel Ticket](https://mediaim.expedia.com/localexpert/48840807/49f0c7f9-d7f7-4281-a580-006a5c5fd53f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago's Navy Pier Centennial Wheel Ticket CA $33 per adult **100%** of travellers recommend [](https://expedia.ca/things-to-do/chicagos-navy-pier-centennial-wheel-ticket.a48840807.activity-details) [See all activities in Chicago](https://expedia.ca/things-to-do/search?rid=800024) ## Explore a world of travel with Expedia - 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