Title: The Loop Vacation Packages & Trips 2025 from CA $674 | 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. ![Hampton Inn & Suites Chicago Medical District UIC](https://images.trvl-media.com/lodging/103000000/102240000/102236700/102236658/03795c9c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hampton Inn & Suites Chicago Medical District UIC Near West Side CA $674 per person Dec 31 - Jan 6 found 7 hours ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.6/10 Exceptional! (246 reviews) Clean room comfy beds and pillows Reviewed on Oct 10, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-31/2026-01-06/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=102236658&paandie=true&dealMarker=ECE-TDp9fdBR_p-FML9EkSgNgRtOhBD85K6fkDsR6Al3kddKctht-vOq1OYZB0RC) ![The Westin Michigan Avenue Chicago](https://images.trvl-media.com/lodging/1000000/30000/21100/21055/dcfbf36b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Michigan Avenue Chicago Downtown Chicago CA $1,071 per person Dec 21 - Dec 26 found 6 hours ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 8.8/10 Excellent! (1,046 reviews) One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done. Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-21/2025-12-26/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21055&paandie=true&dealMarker=eQ41785sc6bOv5L8pbLHTrhs8lMKlVLdqMv5XSdRg-I-PUGdJzDmMQ9SwhSYdRZL) ![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 $1,706 per person Dec 23 - Dec 28 found 18 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Excellent luxury atmosphere with second to none customer service. The bathroom was very nice. Although the toilet has a slight odor that was unexpected for the high quality room and hotel. Reviewed on Oct 15, 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=1723215&paandie=true&dealMarker=nydeEVrW5r1JKFwu4YZKChVqaRXPZMnYf3xUac-1ObbBFmgS85k6ZdW1VoS2fLV8) ![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 $1,034 per person Dec 23 - Dec 28 found 18 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) I loved the hotel, however I would request an inside room next time. It was extremely noisy outside. Reviewed on Oct 11, 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=nydeEVrW5r1JKFwu4YZKCnFyVDUhThO6VopOqu4iZSDdxlFM0OF5Z_0tOQBkWBkW) ![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 $952 per person Nov 15 - Nov 17 found 2 days ago Roundtrip non-stop flight included Toronto (YTZ) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) The front desk staff was super friendly and helpful. After waking up at 4am to catch an early flight, we were thrilled when they had a room ready for us for early check-in. Hyatt does a great job with room lay-outs. It was obvious that our room was recently renovated with a modern conveniences like motorized shades, a comfy window seat, hidden bar and Nespresso maker, and clean decor. Our friends were staying around the corner at the Ritz and liked our room better. Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-15/2025-11-17/?FromAirport=YTZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&dealMarker=slxehwrQ_ERWFZJCZmbwHCnsVeJxDd5YwEkNRMnANlRCv2-PzwOZU1xh_ZhiJQjW) ## 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 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=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Lincoln%20Park&DestID=6059328&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://mediaim.expedia.com/destination/9/ba9d7964e49bf0dfa4a8406e7bf15ec8.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### West Loop Consider a visit to Milwaukee Avenue and take some time to enjoy the abundant dining options during your time in West Loop. If you want to see more of the city, jump on the metro at Racine Station or Ogilvie Transportation Center. [Find hotel + flight trips in West Loop](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=West%20Loop&DestID=553248634029130868&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 $179 CA $210 total Nov 2 - Nov 3 includes taxes & fees 8/10 Very Good! (9,412 reviews) "The person at the registration desk directed me to the wrong tower for my room. He even wrote it on the key holder. Otherwise hotel is fine. Excellent location near the Art Institute, parks and lakefront." Reviewed on Oct 14, 2025 [](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=800024) ![citizenM Chicago Downtown](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/55b627dd_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### citizenM Chicago Downtown 80 East Wacker Place, Chicago, IL Fully refundableReserve now, pay when you stay CA $184 CA $216 total Nov 9 - Nov 10 includes taxes & fees 9.2/10 Wonderful! (3,947 reviews) "Great place with lots to do as it is right I. The downtown, so Riverwalk one at and grant park the other. No outlets by beds so bring long cords" Reviewed on Oct 13, 2025 [](https://expedia.ca/Hotel-Search?startDate=09%2F11%2F2025&endDate=10%2F11%2F2025&selected=82652306&PinnedHotelID=82652306&HadPinnedHotel=true®ionId=800024) ![The Allegro Royal Sonesta Hotel Chicago Loop](https://images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Allegro Royal Sonesta Hotel Chicago Loop 171 W Randolph St, Chicago, IL Fully refundableReserve now, pay when you stay CA $167 CA $241 total Nov 13 - Nov 14 includes taxes & fees 8.8/10 Excellent! (2,129 reviews) "Great location. Small rooms." Reviewed on Oct 14, 2025 [](https://expedia.ca/Hotel-Search?startDate=13%2F11%2F2025&endDate=14%2F11%2F2025&selected=34496&PinnedHotelID=34496&HadPinnedHotel=true®ionId=800024) [See all 1,209 properties in The Loop](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=17%2F10%2F2025&endDate=18%2F10%2F2025®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? > Much less than you might think — from as low as CA $674, in fact! By bundling flights, hotels and car rentals into your own custom-made package, your The Loop escape is only clicks away. ### How do I get a cheap travel package to The Loop? > Booking a hotel and flight together with Expedia won't just save valuable time — it'll save you cash too. A The Loop vacation package makes it easy to organize the perfect trip. With more than 550 airlines all over the world to select from, finding convenient flights that fit your schedule will be no sweat. Not only that, we have over 1,000,000 properties globally to select from. Now that's what you call choice. Whatever your budget, Expedia will help show you the world. ### Where should I stay in The Loop? > A journey to The Loop isn't over until you've seen McCormick Place and Millennium Park. Look for somewhere to stay within walking distance so you can easily access these impressive tourist attractions. ### What are the top hotels in The Loop? > If it's your first time staying in The Loop, make a reservation at [Canopy by Hilton Chicago Central Loop](https://www.expedia.ca/Chicago-Hotels-Canopy-By-Hilton-Chicago-Central-Loop.h68102878.Hotel-Information) or [Hilton Garden Inn Chicago Central Loop](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-Central-Loop.h68102882.Hotel-Information). Both hotels offer comfy beds and are favorites with many travelers. ### How far in advance should I book my The Loop vacation? > To bag rock-bottom prices, book nice and early. Airlines typically advertise flights, along with some of the lowest fares, nearly a year prior to departure. Hotels, car rental and experiences should also be booked well in advance to avoid disappointment. If you were hoping for a last-minute getaway to The Loop, there are always plenty of great deals on Expedia. Check them out now! ### What does an Expedia The Loop travel package include? > That depends on what you want. If you're traveling solo, you might decide to bundle flights and hotels. Taking the whole family to The Loop? A travel package including flights, hotels and rental cars might suit you better. Expedia gives you the freedom to customize your travel package. ### Can I choose my airline with a The Loop Expedia vacation package? > Most definitely. Expedia has over 550 partner airlines to choose from globally. With so many choices, finding the ideal carrier to whisk you away to The Loop will be a snap. ### If I'm not able to travel, can I cancel my The Loop vacation package? > We totally understand that life sometimes gets in the way of your plans. If you've booked a The Loop vacation package and need to cancel or change it, we're here to help. We recommend browsing our [Customer Service Portal](https://www.expedia.ca/service/?langid=4105) first for information. But generally speaking, if you've booked your package in the last 24 hours, you may be able to cancel and rebook for free. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge. ### 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) ![Art Institute of Chicago which includes interior views and art](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24557-Art-Institute-Of-Chicago.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Art Institute of Chicago Explore a massive collection of works celebrating different cultures and historical times, from ancient Egypt to modern installations. [](https://expedia.ca/Art-Institute-Of-Chicago-Downtown-Chicago.d6064021.Vacation-Attraction) ### Things to do ![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=800024) ## Explore a world of travel with Expedia - 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