Title: The Loop Vacation Packages & Trips 2025 from CA $762 | 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. ![Hilton Orrington / Evanston](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/fbf21c1c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Orrington / Evanston Downtown Evanston CA $762 per person Dec 27 - Jan 1 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 7.6/10 Good! (1,003 reviews) Clean rooms, great location in Evanston near the university. Helpful staff. Reviewed on Nov 17, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-27/2026-01-01/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19722&paandie=true&dealMarker=aOtLLqDuBw22ROXCI5AOhhShubUNzDOx70lRnGQtdG5du2MCFyu4daCper4mFO-a) ![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 $1,597 per person Dec 27 - Jan 1 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.6/10 Exceptional! (1,006 reviews) This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend! Reviewed on Oct 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-27/2026-01-01/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&dealMarker=aOtLLqDuBw22ROXCI5AOhmSWgY4MqBoUlfmaE3CQxp2rPI9qXKpavckocvnHMm5T) ![Chicago Athletic Association, a Hyatt Hotel](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118328/6b24bc12_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Chicago Athletic Association, a Hyatt Hotel Downtown Chicago CA $858 per person Dec 26 - Jan 1 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 18/10 Exceptional! (1,002 reviews) Great stay as always- beautiful property, rooms, Game Room is a gem, and excellent staff; just a couple notes: Bring back The Milk Room! The lobby seating was less inviting with so much turned over to assigned-seating dining. Can the hotel offer at least complimentary coffee/tea for guests? I prepaid for breakfast but still had to pay $5 per cup of coffee. Reviewed on Nov 9, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2026-01-01/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1118328&paandie=true&dealMarker=aOtLLqDuBw22ROXCI5AOhlSDNfxwkIUXs3NSOJ0RHpxEvJNfuiX4tg0ZqJCUTQSb) ![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 $1,884 per person Dec 27 - Jan 1 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 18.8/10 Exceptional! (1,001 reviews) Beautiful place and service Reviewed on Oct 29, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-27/2026-01-01/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2717582&paandie=true&dealMarker=aOtLLqDuBw22ROXCI5AOhrmpp3CQrfhybhajhG_PcD44Q0XljhghCKWvqt0QgjyA) ![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago - River North Downtown Chicago CA $1,078 per person Dec 27 - Jan 1 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 18/10 Exceptional! (757 reviews) The room was very clean and the kitchen was well equipped with everything needed to cook meals. Loved the big windows. The bedroom had a dresser with lots of drawers and the closet had lots of shelves and hanging space. The parking garage was so convenient and you were assigned a parking space which so you didn;t have to search for a space and could easily remember where you parked. The only negative was the shower water pressure was very low. The location was within walking distance to restaurants and shopping. We would definitely stay there again. Reviewed on Nov 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-27/2026-01-01/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=74500458&paandie=true&dealMarker=aOtLLqDuBw22ROXCI5AOhsMkEOwih653CKtCmxn4AxSO7R6sARGnaKN4MbdNoHtI) ## 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) ![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) ## 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 $148 CA $209 total Nov 25 - Nov 26 includes taxes & fees 8.4/10 Very Good! (2,066 reviews) Breakfast was good (although not free but it was worthwhile), parking across the street was secured at desk making departure easier, architecture was beautiful and room was comfortable. Would stay in the hotel again Reviewed on Nov 17, 2025 [](https://expedia.ca/Hotel-Search?startDate=25%2F11%2F2025&endDate=26%2F11%2F2025&selected=8079&PinnedHotelID=8079&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 $148 CA $174 total Nov 19 - Nov 20 includes taxes & fees 9.2/10 Wonderful! (4,030 reviews) Modern, super European, petite but very Reviewed on Nov 12, 2025 [](https://expedia.ca/Hotel-Search?startDate=19%2F11%2F2025&endDate=20%2F11%2F2025&selected=82652306&PinnedHotelID=82652306&HadPinnedHotel=true®ionId=800024) ![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 $142 CA $167 total Nov 19 - Nov 20 includes taxes & fees 8/10 Very Good! (9,582 reviews) View and location were awesome. Room and hotel were clearly dated both good and bad. Overall good but missing some modern amenities like air conditioning or climate control Reviewed on Nov 17, 2025 [](https://expedia.ca/Hotel-Search?startDate=19%2F11%2F2025&endDate=20%2F11%2F2025&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=800024) [See all 1,242 properties in The Loop](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=19%2F11%2F2025&endDate=20%2F11%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 $762, 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 4.5/5(722 reviews) 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 4.5/5(149 reviews) 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 4.5/5(304 reviews) 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/feac7bb1-c7ea-4b19-8342-818eafa34e83.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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Daley Center](https://www.expedia.ca/Car-Rentals-In-Richard-J-Daley-Center.d6175173.Car-Rental-Guide) - [Chicago Vacation Rentals](https://www.expedia.ca/Chicago-Vacation-Rentals.d178248.Travel-Guide-VacationRentals) - [Things to do in Chicago](https://www.expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.