Title: South Loop Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $1,279 Expedia.ca [South Loop Travel Guide](https://expedia.ca/Chicago-South-Loop.dx6130108)[Hotels in South Loop](https://expedia.ca/South-Loop-Chicago-Hotels.0-n6130108-0.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)[South Loop Car Rentals](https://expedia.ca/Car-Rentals-In-South-Loop.d6130108.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6130108/f1bd0360-1400-4c1c-882e-1779972b657f.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # South 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 South Loop Price found within the past 48 hours. Click for updated prices. ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $1,279 per person May 21 - May 26 found 1 day ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 9.2/10 Wonderful! (421 reviews) 10/10 makes you feel at home. One of the best hotels I’ve ever stayed in. Reviewed on Mar 23, 2026 ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago CA $1,701 per person Jun 3 - Jun 8 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,401 reviews) Clean perfect view rooms. Convenient to enjoy navy pier. Reviewed on Mar 28, 2026 ![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 $1,757 per person Jun 3 - Jun 8 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) This is the best hotel I’ve been so far, their staffs were supper nice and their rooms are amazing, thanks Reviewed on Mar 28, 2026 ![Thompson Chicago, by Hyatt](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/8920c075_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Thompson Chicago, by Hyatt Downtown Chicago CA $1,516 per person May 21 - May 26 found 1 day ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 9.2/10 Wonderful! (1,332 reviews) Our stay at the Thompson was perfect! Very friendly staff! I strongly recommend a corner room with the city view on the highest floor that you can and trust me you can’t miss Reviewed on Mar 27, 2026 ![The Chicago Hotel Collection - Wrigleyville](https://images.trvl-media.com/lodging/24000000/23610000/23604900/23604891/441ad9d1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Chicago Hotel Collection - Wrigleyville Lakeview CA $1,635 per person May 2 - May 9 found 5 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 7/10 Good! (974 reviews) Excellent location. Clean rooms Reviewed on Mar 24, 2026 ## Where to stay in South Loop Find the best South Loop areas and neighborhoods for the activities you enjoy most. [Learn more about South Loop](https://expedia.ca/Chicago-South-Loop.dx6130108) ![Downtown Chicago](https://images.trvl-media.com/place/6350699/f8ae2db6-94cc-4898-aa46-e275588c3787.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](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) ![The Loop](https://images.trvl-media.com/place/800024/9e323a45-98da-4519-b5ca-71275e70174f.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### The Loop 4.5/5(733 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=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=The%20Loop&DestID=800024&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(39 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) ![River North](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) ## South Loop Hotel Deals ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2_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 $159 CA $187 total Apr 5 - Apr 6 includes taxes & fees 8/10 Very Good! (9,996 reviews) Small rooms Reviewed on Mar 28, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=6130108) ![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 $221 CA $300 total Apr 1 - Apr 2 includes taxes & fees 8.6/10 Excellent! (2,708 reviews) The breakfast was great. Rooms were spotless and the double room had two bathrooms that was great when sharing with a friend Reviewed on Mar 27, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F04%2F2026&endDate=02%2F04%2F2026&selected=12570&PinnedHotelID=12570&HadPinnedHotel=true®ionId=6130108) ![Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/21200/21142/b975595d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel 500 South Dearborn Street Chicago IL Fully refundableReserve now, pay when you stay CA $207 CA $243 total Apr 5 - Apr 6 includes taxes & fees 9.6/10 Exceptional! (1,223 reviews) Great hotel for the price. Our room was clean, had a comfy bed, and was quite large with a king size bed. There were limited ammenities at the hotel, but good food and coffee was a quick walk away. We really enjoyed the Jazz Showcase (2 blocks) and the neighborhood wine bar (2 blocks). Reviewed on Mar 26, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=21142&PinnedHotelID=21142&HadPinnedHotel=true®ionId=6130108) [See all 4,653 properties in South Loop](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=29%2F03%2F2026&endDate=30%2F03%2F2026®ionId=6130108) 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 South Loop vacation package cost? ### How do I get a cheap travel package to South Loop? ### Where should I stay in South Loop? ### What are the top hotels in South Loop? ### How far in advance should I book my South Loop vacation? ### What does an Expedia South Loop travel package include? ### What should I know before booking a South Loop travel package? ### Can I choose my airline with a South Loop Expedia vacation package? ### If I'm not able to travel, can I cancel my South Loop vacation package? ### Things to do ![360 CHICAGO Observation Deck ](https://mediaim.expedia.com/localexpert/170348/1cbf6a0b-f355-4f8a-a858-37fdc0668a64.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 360 CHICAGO Observation Deck CA $37 per adult **86%** of travellers recommend [](https://expedia.ca/things-to-do/360-chicago-observation-deck.a170348.activity-details) ![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) [See all activities in Chicago](https://expedia.ca/things-to-do/search?rid=6130108) ## Explore a world of travel with Expedia - 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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) - [Visit Near South Side ](https://www.expedia.ca/Chicago-Near-South-Side.dx6132399) - [Visit Prairie District ](https://www.expedia.ca/Chicago-Prairie-District.dx553248635976473159) - [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) - [Chicago Vacations ](https://www.expedia.ca/Chicago.d178248.Destination-Travel-Guides) - [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) - [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) - [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) - [United Center ](https://www.expedia.ca/United-Center-Near-West-Side.d6064077.Vacation-Attraction) - [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) - [Budget Rental Cars in Central Station ](https://www.expedia.ca/Budget-Car-Rentals-In-Central-Station.d6132250-c39.Car-Rental-Guide-Suppliers) - [Car rentals near Chicago ](https://www.expedia.ca/Car-Rentals-In-Chicago.d178248.Car-Rental-Guide) - [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.