Title: Downtown Chicago Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $618 Expedia.ca [Downtown Chicago Travel Guide](https://expedia.ca/Chicago-Downtown-Chicago.dx6350699)[Hotels in Downtown Chicago](https://expedia.ca/Downtown-Chicago-Chicago-Hotels.0-n6350699-0.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)[Downtown Chicago Car Rentals](https://expedia.ca/Car-Rentals-In-Downtown-Chicago.d6350699.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6350699/f8ae2db6-94cc-4898-aa46-e275588c3787.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Downtown Chicago 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 Downtown Chicago 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 17 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 7 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 6 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 24 hours 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 24 hours 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 Downtown Chicago Find the best Downtown Chicago areas and neighborhoods for the activities you enjoy most. [Learn more about Downtown Chicago](https://expedia.ca/Chicago-Downtown-Chicago.dx6350699) ![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) ![The Loop - Downtown featuring a river or creek](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/192000/192013-The-Loop-Downtown.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### The Loop 4.5/5(725 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) ![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) ## Downtown Chicago Hotel Deals ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago/Magnificent Mile Suites 198 E Delaware Pl Chicago IL Fully refundableReserve now, pay when you stay CA $123 CA $144 total Jan 11 - Jan 12 includes taxes & fees 8.8/10 Excellent! (3,609 reviews) Spotless room, very nice staff Reviewed on Dec 29, 2025 [](https://expedia.ca/Hotel-Search?startDate=11%2F01%2F2026&endDate=12%2F01%2F2026&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true®ionId=6350699) ![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=6350699) ![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! (2,417 reviews) Check in staff were great and room was clean. Worst part was house cleaner knocking at door at 1030am, after being up till 2am night before have a good time at football game. Hot tub amazing and our view! Reviewed on Dec 27, 2025 [](https://expedia.ca/Hotel-Search?startDate=11%2F01%2F2026&endDate=12%2F01%2F2026&selected=12570&PinnedHotelID=12570&HadPinnedHotel=true®ionId=6350699) [See all 1,709 properties in Downtown Chicago](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=03%2F01%2F2026&endDate=04%2F01%2F2026®ionId=6350699) 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 Downtown Chicago vacation package cost? ### How do I get a cheap travel package to Downtown Chicago? ### How far in advance should I book my Downtown Chicago vacation? ### What does an Expedia Downtown Chicago travel package include? ### What should I know before booking a Downtown Chicago travel package? ### Can I choose my airline with a Downtown Chicago Expedia vacation package? ### If I'm not able to travel, can I cancel my Downtown Chicago vacation package? ### Discover the most popular places to visit in Downtown Chicago ![Magnificent Mile - River North which includes signage, a city and night scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23728-Magnificent-Mile.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Michigan Avenue You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants. [](https://expedia.ca/Michigan-Avenue-Downtown-Chicago.d6156167.Vacation-Attraction) ![Navy Pier](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54738-Navy-Pier-Chicago.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Navy Pier A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district. [](https://expedia.ca/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction) ![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) ### 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=6350699) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - [Hotels near Aon Center ](https://www.expedia.ca/Aon-Center-Hotels.0-l6064015-0.Travel-Guide-Filter-Hotels) - [Hotels near Art Institute of Chicago ](https://www.expedia.ca/Art-Institute-Of-Chicago-Hotels.0-l6064021-0.Travel-Guide-Filter-Hotels) - [Hotels near Carbide and Carbon Building ](https://www.expedia.ca/Carbide-And-Carbon-Building-Hotels.0-l553248621555594910-0.Travel-Guide-Filter-Hotels) - [Aparthotels in Central Chicago ](https://www.expedia.ca/Central-Chicago-Apart-Hotels.d553248635976475413-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Central Chicago ](https://www.expedia.ca/Central-Chicago-Bed-And-Breakfast.d553248635976475413-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Central Chicago ](https://www.expedia.ca/Central-Chicago-Guest-Houses.d553248635976475413-aaGuestHouses.Travel-Guide-Accommodation) - [Hostels in Central Chicago ](https://www.expedia.ca/Central-Chicago-Hostels.d553248635976475413-aaHostels.Travel-Guide-Accommodation) - [Kimpton Hotels in Central Chicago ](https://www.expedia.ca/Central-Chicago-Hotels-Kimpton-Hotels.0-0-d553248635976475413--bKimptonHotels.Travel-Guide-Filter-Hotels) - [Marriott Hotels & Resorts in Central Chicago ](https://www.expedia.ca/Central-Chicago-Hotels-Marriott-Hotels-Resorts.0-0-d553248635976475413--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels) - [Central Chicago Hotels ](https://www.expedia.ca/Central-Chicago-Hotels.d553248635976475413.Travel-Guide-Hotels) - [Cheap Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Cheap-Hotels.0-0-d178248-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in Chicago ](https://www.expedia.ca/Chicago-Hotels-Hotels-With-Free-Parking.0-0-d178248-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Marriott Hotels & Resorts in Chicago ](https://www.expedia.ca/Chicago-Hotels-Marriott-Hotels-Resorts.0-0-d178248--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels) - [Chicago Hotels ](https://www.expedia.ca/Chicago-Hotels.d178248.Travel-Guide-Hotels) - [Hotels near Chicago Riverwalk ](https://www.expedia.ca/Chicago-Riverwalk-Hotels.0-l553248621533116610-0.Travel-Guide-Filter-Hotels) - [Hotels near Chicago Theatre ](https://www.expedia.ca/Chicago-Theatre-Hotels.0-l6064049-0.Travel-Guide-Filter-Hotels) - [Hotels near Cloud Gate ](https://www.expedia.ca/Cloud-Gate-Hotels.0-l6182888-0.Travel-Guide-Filter-Hotels) - [Hotels near Harris Theater ](https://www.expedia.ca/Harris-Theater-Hotels.0-l6182886-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Lakeshore East ](https://www.expedia.ca/Lakeshore-East-Chicago-Hotels-Cheap-Hotels.0-n553248635976472445-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Lakeshore East ](https://www.expedia.ca/Lakeshore-East-Chicago-Hotels-Luxury-Hotel.0-n553248635976472445-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Marriott Hotels & Resorts in Lakeshore East ](https://www.expedia.ca/Lakeshore-East-Chicago-Hotels-Marriott-Hotels-Resorts.0-n553248635976472445-0--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels) - [Lakeshore East Hotels ](https://www.expedia.ca/Lakeshore-East-Chicago-Hotels.0-n553248635976472445-0.Travel-Guide-Filter-Hotels) - [Hotels near London Guarantee Building ](https://www.expedia.ca/London-Guarantee-Building-Hotels.0-l553248621555594906-0.Travel-Guide-Filter-Hotels) - [Hotels near Maggie Daley Park ](https://www.expedia.ca/Maggie-Daley-Park-Hotels.0-l6182884-0.Travel-Guide-Filter-Hotels) - [Magnificent Mile Hotels ](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels.0-n800025-0.Travel-Guide-Filter-Hotels) - [Hotels near Michigan Avenue Bridge ](https://www.expedia.ca/Michigan-Avenue-Bridge-Hotels.0-l6069197-0.Travel-Guide-Filter-Hotels) - [Hotels near Michigan Avenue ](https://www.expedia.ca/Michigan-Avenue-Hotels.0-l6156167-0.Travel-Guide-Filter-Hotels) - [Hotels near Millennium Park ](https://www.expedia.ca/Millennium-Park-Hotels.0-l6069201-0.Travel-Guide-Filter-Hotels) - [Guest Houses in Millennium Station ](https://www.expedia.ca/Millennium-Station-Guest-Houses.d6129922-aaGuestHouses.Travel-Guide-Accommodation) - [Hotels near Millennium Station ](https://www.expedia.ca/Millennium-Station-Hotels.d6129922.Travel-Guide-Hotels) - [Resorts in Millennium Station ](https://www.expedia.ca/Millennium-Station-Resort-Hotels.d6129922-aaResortHotels.Travel-Guide-Accommodation) - [Business Hotels in Near East Side ](https://www.expedia.ca/Near-East-Side-Chicago-Hotels-Business-Hotel.0-n553248633938968461-0-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Near East Side ](https://www.expedia.ca/Near-East-Side-Chicago-Hotels-Cheap-Hotels.0-n553248633938968461-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Near East Side ](https://www.expedia.ca/Near-East-Side-Chicago-Hotels-Romantic-Hotel.0-n553248633938968461-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Near East Side Hotels ](https://www.expedia.ca/Near-East-Side-Chicago-Hotels.0-n553248633938968461-0.Travel-Guide-Filter-Hotels) - [Hotels near Pritzker Pavilion ](https://www.expedia.ca/Pritzker-Pavilion-Hotels.0-l6064057-0.Travel-Guide-Filter-Hotels) - [Aparthotels in Randolph-Wabash Station ](https://www.expedia.ca/Randolph-Wabash-Station-Apart-Hotels.d6210237-aaApartHotels.Travel-Guide-Accommodation) - [Hotels near Randolph-Wabash Station ](https://www.expedia.ca/Randolph-Wabash-Station-Hotels.d6210237.Travel-Guide-Hotels) - [River North Hotels ](https://www.expedia.ca/River-North-Chicago-Hotels.0-n6350695-0.Travel-Guide-Filter-Hotels) - [Hotels near Ronald McDonald House near Lurie Children’s ](https://www.expedia.ca/Ronald-McDonald-House-Near-Lurie-Childrens-Hotels.0-l553248635921782888-0.Travel-Guide-Filter-Hotels) - [Streeterville Hotels ](https://www.expedia.ca/Streeterville-Chicago-Hotels.0-n6130109-0.Travel-Guide-Filter-Hotels) - [The Loop Hotels ](https://www.expedia.ca/The-Loop-Chicago-Hotels.0-n800024-0.Travel-Guide-Filter-Hotels) - [Hotels near Tribune Tower ](https://www.expedia.ca/Tribune-Tower-Hotels.0-l6064075-0.Travel-Guide-Filter-Hotels) - [Hotels near Wrigley Building ](https://www.expedia.ca/Wrigley-Building-Hotels.0-l6064091-0.Travel-Guide-Filter-Hotels) - [Flights to Central Chicago ](https://www.expedia.ca/Cheap-Flights-To-Central-Chicago.d553248635976475413.Travel-Guide-Flights) - [Flights to Chicago ](https://www.expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights) - [Flights from Toronto (YYZ) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago) - [900 North Michigan Shops ](https://www.expedia.ca/900-North-Michigan-Shops-Downtown-Chicago.d6199347.Vacation-Attraction) - [Ann and Robert H. 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) - [Chicago Harbor Lighthouse ](https://www.expedia.ca/Chicago-Harbor-Lighthouse-Chicago.d6064039.Vacation-Attraction) - [Chicago History Museum ](https://www.expedia.ca/Chicago-History-Museum-Lincoln-Park.d6064041.Vacation-Attraction) - [Visit Magnificent Mile ](https://www.expedia.ca/Chicago-Magnificent-Mile.dx800025) - [Chicago Riverwalk ](https://www.expedia.ca/Chicago-Riverwalk-Downtown-Chicago.d553248621533116610.Vacation-Attraction) - [Visit Streeterville ](https://www.expedia.ca/Chicago-Streeterville.dx6130109) - [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) - [Visit Chicago ](https://www.expedia.ca/Chicago.dx178248) - [Cloud Gate ](https://www.expedia.ca/Cloud-Gate-Downtown-Chicago.d6182888.Vacation-Attraction) - [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) - [International Museum of Surgical Science ](https://www.expedia.ca/International-Museum-Of-Surgical-Science-Downtown-Chicago.d6065139.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) - [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) - [Avis Rental Cars in Central Chicago ](https://www.expedia.ca/Avis-Car-Rentals-In-Central-Chicago.d553248635976475413-c41.Car-Rental-Guide-Suppliers) - [Car rentals near Chicago ](https://www.expedia.ca/Car-Rentals-In-Chicago.d178248.Car-Rental-Guide) - [Car rentals near Michigan Avenue ](https://www.expedia.ca/Car-Rentals-In-Michigan-Avenue.d6156167.Car-Rental-Guide) - [Car rentals near Millennium Park ](https://www.expedia.ca/Car-Rentals-In-Millennium-Park.d6069201.Car-Rental-Guide) - [Economy Car Rentals in Central Chicago ](https://www.expedia.ca/Economy-Car-Rentals-In-Central-Chicago.d553248635976475413-tEconomy.Car-Rental-Guide-Class) - [Enterprise Rental Cars in Central Chicago ](https://www.expedia.ca/Enterprise-Car-Rentals-In-Central-Chicago.d553248635976475413-c15.Car-Rental-Guide-Suppliers) - [Fox Rental Cars Rental Cars in Central Chicago ](https://www.expedia.ca/Fox-Rental-Cars-Car-Rentals-In-Central-Chicago.d553248635976475413-c19.Car-Rental-Guide-Suppliers) - [Full-Size Car Rentals in Central Chicago ](https://www.expedia.ca/Fullsize-Car-Rentals-In-Central-Chicago.d553248635976475413-tFullsize.Car-Rental-Guide-Class) - [Full-Size Car Rentals near Millennium Park ](https://www.expedia.ca/Fullsize-Car-Rentals-In-Millennium-Park.d6069201-tFullsize.Car-Rental-Guide-Class) - [Mini Car Rentals near Millennium Park ](https://www.expedia.ca/Mini-Car-Rentals-In-Millennium-Park.d6069201-tMini.Car-Rental-Guide-Class) - [Minivan Car Rentals in Central Chicago ](https://www.expedia.ca/Minivan-Car-Rentals-In-Central-Chicago.d553248635976475413-tMinivan.Car-Rental-Guide-Class) - [National Car Rental Rental Cars in Central Chicago ](https://www.expedia.ca/National-Car-Rental-Car-Rentals-In-Central-Chicago.d553248635976475413-c42.Car-Rental-Guide-Suppliers) - [Payless Rental Cars in Central Chicago ](https://www.expedia.ca/Payless-Car-Rentals-In-Central-Chicago.d553248635976475413-c38.Car-Rental-Guide-Suppliers) - [Pickup Car Rentals near Millennium Park ](https://www.expedia.ca/Pickup-Car-Rentals-In-Millennium-Park.d6069201-tPickup.Car-Rental-Guide-Class) - [Suv Car Rentals near Millennium Park ](https://www.expedia.ca/SUV-Car-Rentals-In-Millennium-Park.d6069201-tSUV.Car-Rental-Guide-Class) - [Sixt Rental Cars in Central Chicago ](https://www.expedia.ca/Sixt-Car-Rentals-In-Central-Chicago.d553248635976475413-c35.Car-Rental-Guide-Suppliers) - [Van Car Rentals near Millennium Park ](https://www.expedia.ca/Van-Car-Rentals-In-Millennium-Park.d6069201-tVan.Car-Rental-Guide-Class) - [Things to do in Central Chicago ](https://www.expedia.ca/Things-To-Do-In-Central-Chicago.d553248635976475413.Travel-Guide-Activities) - [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.