Title: Central Chicago Vacation Packages & Trips 2026 from CA $507 | Expedia.ca [Central Chicago Travel Guide](https://expedia.ca/Central-Chicago.dx553248635976475413)[Hotels in Central Chicago](https://expedia.ca/Central-Chicago-Hotels.d553248635976475413.Travel-Guide-Hotels)[Vacation Rentals in Central Chicago](https://expedia.ca/Central-Chicago-Vacation-Rentals.d553248635976475413.Travel-Guide-VacationRentals)[Flights to Central Chicago](https://expedia.ca/Cheap-Flights-To-Central-Chicago.d553248635976475413.Travel-Guide-Flights)[Things to do in Central Chicago](https://expedia.ca/Things-To-Do-In-Central-Chicago.d553248635976475413.Travel-Guide-Activities)[Central Chicago Car Rentals](https://expedia.ca/Car-Rentals-In-Central-Chicago.d553248635976475413.Car-Rental-Guide) ![](https://images.trvl-media.com/place/829/bd91735e-0c7e-4d0c-8152-a9d6fd38ff30.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Central Chicago Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Phil Ostroff - ## 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 Central Chicago Vacation Deals 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 $507 per person Feb 17 - Feb 21 found 2 hours ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 7.6/10 Good! (1,002 reviews) Clean rooms, great location in Evanston near the university. Helpful staff. Reviewed on Nov 17, 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 $1,902 per person Jan 31 - Feb 6 found 6 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) One of the best, if not the best we have ever stayed at. Staff were exceptional including Osama who made us welcome from the moment we arrived. Outstanding!! Reviewed on Dec 15, 2025 ![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 $808 per person Jan 31 - Feb 6 found 6 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Concierge not helpful and neither is was the door man, Neither would get me a cab, they said to just stand outside Reviewed on Dec 4, 2025 ![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 $988 per person Feb 23 - Feb 27 found 17 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom. Reviewed on Dec 14, 2025 ![Radisson Blu Aqua Hotel Chicago](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/8cd3425b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Radisson Blu Aqua Hotel Chicago Downtown Chicago CA $725 per person Jan 31 - Feb 6 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 8.6/10 Excellent! (1,761 reviews) Hotel was amazing all around! Friendly and very helpful staff. Clean rooms and a Starbucks! Reviewed on Dec 14, 2025 ## Where to stay in Central Chicago Find the best Central Chicago areas and neighborhoods for the activities you enjoy most. [Learn more about Central Chicago](https://expedia.ca/Central-Chicago.dx553248635976475413) ![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 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) ![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=350&h=192&q=medium) ### Near North Side 4.5/5(820 area reviews) Michigan Avenue and Navy Pier are a few top attractions in Near North Side. Hop around the city on the metro at Clark-Division Station or Chicago Station (Brown Line) and check out the area's fascinating museums, panoramic lake views, and popular shops. [Find hotel + flight trips in Near North Side](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Near%20North%20Side&DestID=137043&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Ready to book your vacation to Central Chicago? Choose your dates ## Central 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 $112 CA $131 total Jan 5 - Jan 6, 2026 includes taxes & fees 8.8/10 Excellent! (3,464 reviews) I love the big asize of the room. The bed was comfortable. The room temperature was warm and pleasant even as it snowed outside the windows. The only downside would be when I went to watch the Sunday night Bears and Packers football game down at the bar. The young and bearded bartender swore like ... Reviewed on Dec 11, 2025 [](https://expedia.ca/Hotel-Search?startDate=05%2F01%2F2026&endDate=06%2F01%2F2026&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true®ionId=553248635976475413) ![Silversmith Hotel Chicago Downtown](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Silversmith Hotel Chicago Downtown 10 S Wabash Ave Chicago IL Fully refundableReserve now, pay when you stay CA $111 CA $173 total Jan 4 - Jan 5, 2026 includes taxes & fees 9.2/10 Wonderful! (2,120 reviews) Beautiful old hotel convenient to downtown . Wonderful rooms and great onsite dining. You can hear the trains outside from pretty much every room but I found it acceptable noise level. Reviewed on Dec 13, 2025 [](https://expedia.ca/Hotel-Search?startDate=04%2F01%2F2026&endDate=05%2F01%2F2026&selected=116674&PinnedHotelID=116674&HadPinnedHotel=true®ionId=553248635976475413) ![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 $150 CA $211 total Dec 30 - Dec 31 includes taxes & fees 8.4/10 Very Good! (2,134 reviews) Clean room. I didn’t mind the old door knobs I liked it. Smaller room than anticipated but it was nice and clean. Reviewed on Dec 14, 2025 [](https://expedia.ca/Hotel-Search?startDate=30%2F12%2F2025&endDate=31%2F12%2F2025&selected=8079&PinnedHotelID=8079&HadPinnedHotel=true®ionId=553248635976475413) [See all 1,494 properties in Central Chicago](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=17%2F12%2F2025&endDate=18%2F12%2F2025®ionId=553248635976475413) 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) ### Discover the most popular places to visit in Central 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 4.5/5(19 reviews) 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 4.5/5(459 reviews) 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 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) ### What to do in Central Chicago ![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 **96%** of travellers recommend [](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.activity-details) ![cruise ship sailing past navy pier in chicago](https://mediaim.expedia.com/localexpert/173241/21d8d1a0-e61c-4298-ab2f-118c1794b450.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### City Cruises Chicago: Lake Michigan Premier Dinner Cruise CA $281 per adult **80%** of travellers recommend [](https://expedia.ca/things-to-do/city-cruises-chicago-lake-michigan-premier-dinner-cruise.a173241.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 Central Chicago](https://expedia.ca/things-to-do/search?rid=553248635976475413) ## Frequently asked questions ### Can I cancel my flight booking to Central Chicago due to COVID-19? ### What's the best way to find cheap flights to Central Chicago that have flexible change policies? ### What are some of the general tips for travelers to Central Chicago during the COVID-19 outbreak? > - Research if any travel restrictions apply to your destination and origin before booking your flight. Also check if there are any requirements you'll have to follow on arrival, such as health testing. > - Requirements state that you must wear a face mask at the airport, including at security checkpoints. You should be prepared to lower your mask for ID purposes when asked by a TSA employee. > - Avoid handing your boarding pass (electronic or paper) directly to a TSA officer. Instead, position the pass on the scanner and then hold it up for inspection. > - You are now allowed to take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on luggage. You'll have to remove it for screening. > - Empty your personal items from your pockets, like your wallet and phone, and put them in your carry-on instead of into bins. This will minimize handling during screening. > - Transport all food items in a clear plastic bag and also put them in a screening bin. Separating food from your carry-on means it's less likely a TSA employee will need to open and touch your bag for inspection. ### Which airlines fly to Central Chicago? ### How can I find cheap tickets to Central Chicago? ### How much is a flight to Central Chicago? ### What are the most popular airports to fly into in Central Chicago? ### When is the cheapest time to fly to Central Chicago? ### How much is a plane ticket to Central Chicago? ### Which airlines with flights to Central Chicago employ COVID-19 cleanliness policies? > - United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant. > - American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant. > - Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - [2 Star Hotels in Downtown Chicago ](https://www.expedia.ca/2Star-Downtown-Chicago-Chicago-Hotels.s20-n6350699-0.Travel-Guide-Filter-Hotels) - 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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) - [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) - [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 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) - [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) - [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) - [Car rentals near Chicago ](https://www.expedia.ca/Car-Rentals-In-Chicago.d178248.Car-Rental-Guide) - [Car rentals near Downtown Chicago ](https://www.expedia.ca/Car-Rentals-In-Downtown-Chicago.d6350699.Car-Rental-Guide) - [Car rentals near Michigan Avenue ](https://www.expedia.ca/Car-Rentals-In-Michigan-Avenue.d6156167.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. 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