Title: The Loop Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $705 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. ![Chez Hotel Arlington Heights](https://images.trvl-media.com/lodging/102000000/101050000/101044900/101044822/9b222c7c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Chez Hotel Arlington Heights CA $705 per person May 6 - May 10 found 15 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (500 reviews) My introduction to this hotel came through social media platforms TikTok and Instagram, where promotional videos showcased its attractive features. This led us to book a stay. Upon entering the lobby, I was impressed by its chic decor and beautiful interior design. However, the hallways leading to the rooms were marred by a strong smell of marijuana, which detracted from the overall experience. Although the rooms were visually appealing, they lacked depth, and several issues arose, including a bathroom door that would not close and a sink with slow drainage. The bedsheet also kept coming off, despite housekeeping services. When inquiring about checkout time and a possible extension, I received conflicting information from the staff. Initially, I was informed that the latest checkout time was 11:30 AM, whereas a subsequent inquiry revealed that the complimentary extension was actually until 12 PM. This discrepancy raised questions about the staff's consistency and willingness to accommodate guests. Moreover, the absence of ice machines on the floors and the need to visit the main floor to obtain ice, which was then provided by the staff, struck me as unusual. We will not be staying here again. Reviewed on Feb 16, 2026 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago CA $1,348 per person Apr 1 - Apr 4 found 1 day ago Roundtrip flight included Montreal (YMQ) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better. Reviewed on Jan 26, 2026 ![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 $912 per person Apr 20 - Apr 24 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Chicago (ORD) 9/10 Wonderful! (380 reviews) My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone! Reviewed on Feb 2, 2026 ![Viceroy Chicago](https://images.trvl-media.com/lodging/19000000/18620000/18614200/18614145/3aeed14b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Viceroy Chicago Downtown Chicago CA $835 per person Apr 8 - Apr 11 found 14 hours ago Roundtrip flight included Montreal (YMQ) to Chicago (ORD) 9.4/10 Exceptional! (1,129 reviews) We stayed at the Viceroy Chicago last night and had a wonderful experience. The hotel is stylish, comfortable, and feels thoughtfully designed in every detail. The staff was warm and welcoming from the moment we arrived, and the service throughout our stay was excellent. Our room was spotless with a great layout, and the overall atmosphere of the hotel made it easy to relax and enjoy the night. A really lovely stay—highly recommend. Reviewed on Feb 15, 2026 ![Staybridge Suites Chicago-Oakbrook Terrace by IHG](https://images.trvl-media.com/lodging/1000000/880000/879700/879633/653d07be_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Staybridge Suites Chicago-Oakbrook Terrace by IHG York Center CA $748 per person Mar 28 - Apr 4 found 13 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.2/10 Very Good! (1,000 reviews) Breakfast was good. Separate bedroom and living room. Kitchen with stove and basic utensils with dishwasher. Renovation of the property is in progress hope to see some improved quality of beds and stove with increased in-premise Parking slots for all guests. Overall had a pleasant stay. Reviewed on Feb 16, 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://images.trvl-media.com/place/6350699/f8ae2db6-94cc-4898-aa46-e275588c3787.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Downtown Chicago 4 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://images.trvl-media.com/place/800025/2f4bc1ac-f370-4b72-8a89-0aa7dcb93f0c.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) ![River North showing railway items, street scenes and a city](https://images.trvl-media.com/place/6350695/b009c703-f7ab-4e4c-95a4-4b883071adef.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) ![Underground passage in the Chicago O'Hare airport](https://images.trvl-media.com/place/553248635074842747/1dda5453-2f05-4485-9f3c-404a7075d270.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### O'Hare 3.5/5(38 area reviews) Home to O'Hare International Airport, this transportation hub offers easy access to downtown via the Blue Line. The area also hosts various corporate headquarters and international consulates. [Find hotel + flight trips in O'Hare](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=O%27Hare&DestID=553248635074842747&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Chicago which includes modern architecture and a city](https://images.trvl-media.com/place/6059328/2fb61786-4c0f-40e8-ae4e-a0fad3f9539a.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=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Lincoln%20Park&DestID=6059328&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## The Loop 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 $122 CA $143 total Feb 18 - Feb 19 includes taxes & fees 8/10 Very Good! (9,872 reviews) Room was nice and clean. Hotel had a fantastic classic look and feel. Perfect place to stay for shows at the Auditorium theater across the street. It's a very old building so the heating and hot water situation is a little off compared to newer hotels but nothing that would deter me from staying ... Reviewed on Feb 13, 2026 [](https://expedia.ca/Hotel-Search?startDate=18%2F02%2F2026&endDate=19%2F02%2F2026&selected=6452&PinnedHotelID=6452&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 $189 CA $262 total Feb 27 - Feb 28 includes taxes & fees 8.4/10 Very Good! (2,618 reviews) It was great Reviewed on Feb 12, 2026 [](https://expedia.ca/Hotel-Search?startDate=27%2F02%2F2026&endDate=28%2F02%2F2026&selected=12570&PinnedHotelID=12570&HadPinnedHotel=true®ionId=800024) ![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 $206 CA $276 total Feb 27 - Feb 28 includes taxes & fees 8.4/10 Very Good! (2,288 reviews) They were very accommodating. Reviewed on Feb 15, 2026 [](https://expedia.ca/Hotel-Search?startDate=27%2F02%2F2026&endDate=28%2F02%2F2026&selected=8079&PinnedHotelID=8079&HadPinnedHotel=true®ionId=800024) [See all 1,229 properties in The Loop](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=18%2F02%2F2026&endDate=19%2F02%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://images.trvl-media.com/place/6069201/87d76a1e-e63f-48a2-8892-fb54ee86f8e1.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://images.trvl-media.com/place/553248621533116610/1742d80f-9a94-4104-8fda-70856c757147.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 central business district, a high-rise building and a city](https://images.trvl-media.com/place/6064069/c1ef90d8-49f7-4587-8493-0d8393ea7f31.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 ![Wendella's 90-min Chicago River Architecture Tour](https://mediaim.expedia.com/localexpert/766175/932beb0e-70fe-42a4-baff-df68960da73f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wendella's 90-min Chicago River Architecture Tour CA $55 per adult **94%** of travellers recommend [](https://expedia.ca/things-to-do/wendellas-90-min-chicago-river-architecture-tour.a766175.activity-details) ![Flyover in Chicago](https://mediaim.expedia.com/localexpert/50023979/095bdacd-a8be-4515-aac0-469239aa8c0a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Flyover in Chicago CA $52 per adult **98%** of travellers recommend [](https://expedia.ca/things-to-do/flyover-in-chicago.a50023979.activity-details) ![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) [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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