Title: Sleepy Hollow Vacation Packages & Trips 2025 from CA $434 | Expedia.ca [Hotels in Sleepy Hollow](https://expedia.ca/Sleepy-Hollow-Chicago-Hotels.0-n6132427-0.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)[Sleepy Hollow Car Rentals](https://expedia.ca/Car-Rentals-In-Sleepy-Hollow.d6132427.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Sleepy Hollow 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 Sleepy Hollow Price found within the past 48 hours. Click for updated prices. ![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Grand Vacations Club Chicago Magnificent Mile Downtown Chicago CA $434 per person Feb 20 - Feb 23 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 18.4/10 Exceptional! (317 reviews) I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location. Reviewed on Oct 28, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-20/2026-02-23/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=z6D9kaAeQuoGmNXM2_d5XICauiR7skes0FlRKMJny1N39n0BRyisBIM9PuV35QZV) ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago CA $690 per person Feb 20 - Feb 23 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 18.4/10 Exceptional! (1,264 reviews) Clean, quiet and comfortable room, courteous staff. We received a $25k food credit through Expedia and got exceptional pastries and coffee at the adjacent cafe. Reviewed on Nov 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-20/2026-02-23/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&dealMarker=z6D9kaAeQuoGmNXM2_d5XM9e4sapxzEvtMuMKQH_Nug4ZlvlkSS7GtqjPKaRfrmV) ![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 $547 per person Feb 20 - Feb 23 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 18/10 Exceptional! (380 reviews) Everything was first class, even the coffee shop downstairs. Not to mention the grocery store that is attached to the same building. The ultimate convenience right near the miracle Mile in Chicago, my most favorite place in the world. Reviewed on Nov 25, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-20/2026-02-23/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&dealMarker=z6D9kaAeQuoGmNXM2_d5XH3PQwyZnkU0M_dJqXl6xsgkHnWesR3RkhOXfRhT2_oD) ![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 $1,051 per person Feb 12 - Feb 16 found 20 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 18.8/10 Exceptional! (1,773 reviews) Great stay. Excellent location. Reviewed on Nov 23, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=Gg88dHWJNfqIGGgECQGvtZCs-itu4wJpKYXgw5pu6tkN4_CRIQrBIac9KBcSpuvk) ![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 $453 per person Feb 20 - Feb 23 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 18.8/10 Exceptional! (1,130 reviews) Really great spot in the city right in the middle like a five minute walk to to everything around you the staff was great. The rooms were beautiful. Reviewed on Nov 24, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-20/2026-02-23/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=z6D9kaAeQuoGmNXM2_d5XLZVDTMd57i97z-zFASRKLXr7Who3FyMUy1rP1t8m6eY) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=PKG_BF_PROMO_6132427) ## Where to stay in Sleepy Hollow Find the best Sleepy Hollow areas and neighborhoods for the activities you enjoy most. [Learn more about Sleepy Hollow](https://expedia.ca/Chicago-Sleepy-Hollow.dx6132427) ![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) ![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 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) ## Sleepy Hollow 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 $145 CA $205 total Dec 21 - Dec 22 includes taxes & fees 8.4/10 Very Good! (2,090 reviews) Rooms are small and tile in bathroom looked dirty Reviewed on Nov 24, 2025 [](https://expedia.ca/Hotel-Search?startDate=21%2F12%2F2025&endDate=22%2F12%2F2025&selected=8079&PinnedHotelID=8079&HadPinnedHotel=true®ionId=6132427) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Embassy Suites by Hilton Chicago Downtown River North 600 N State St Chicago IL CA $123 CA $144 total Dec 21 - Dec 22 includes taxes & fees 8.4/10 Very Good! (5,291 reviews) All above. Reviewed on Nov 24, 2025 [](https://expedia.ca/Hotel-Search?startDate=21%2F12%2F2025&endDate=22%2F12%2F2025&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=6132427) ![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 $117 CA $138 total Dec 7 - Dec 8 includes taxes & fees 8.8/10 Excellent! (3,350 reviews) Room was clean and spacious! Reviewed on Nov 23, 2025 [](https://expedia.ca/Hotel-Search?startDate=07%2F12%2F2025&endDate=08%2F12%2F2025&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true®ionId=6132427) [See all 4,907 properties in Sleepy Hollow](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=27%2F11%2F2025&endDate=28%2F11%2F2025®ionId=6132427) 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 Sleepy Hollow vacation package cost? > Get your credit card ready, because a getaway to Sleepy Hollow starts from a tempting CA $434. When you bundle your flights, hotels and more into a package, you'll land the lowest prices. ### How do I get a cheap travel package to Sleepy Hollow? > Book everything in the one place with our Sleepy Hollow vacation packages. We have incredible bargains on hotels, flights, tours and more that'll keep your travel budget happy and your adventurous spirit alive. And, with more than 550 partner airlines and 1,000,000 hotel options around the world to pick from, there are endless opportunities to mix and match as you like. ### Where should I stay in Sleepy Hollow? > There's plenty to do in Sleepy Hollow, so stay near its best attractions and spend more time sightseeing. Balzekas Museum of Lithuanian Culture is one spot to put on your must-see list. ### How far in advance should I book my Sleepy Hollow vacation? > Reserving your flights early with Expedia means one less thing to worry about. A number of air carriers advertise prices up to 12 months in advance. This is usually the cheapest time to book. If circumstances have left you booking late, fantastic last-minute deals to Sleepy Hollow sometimes emerge a few weeks before departure. ### What does an Expedia Sleepy Hollow travel package include? > Expedia has everything you need to lock in Sleepy Hollow trip, but what goes into your package is your call. Select from any combination of rental cars, flights and hotels. Chasing some experiences or tours to keep you on the go? Once you've made your booking, you can add them on too. No matter your style, there's a package to meet your needs. ### What should I know before booking a Sleepy Hollow travel package? > Booking all the parts of your getaway together is a great way to save. Bundle your airfares, rental cars and hotels into a neat package. But your options don't end at hotels. Expedia has all kinds of properties, including vacation rentals like beachside villas and city apartments. You've got choices galore! ### Can I choose my airline with a Sleepy Hollow Expedia vacation package? > Expedia has access to more than 550 airline partners worldwide, so you definitely can. Simply select the carrier that suits you and craft your ideal Sleepy Hollow getaway. ### If I'm not able to travel, can I cancel my Sleepy Hollow vacation package? > Certainly, and we'll help you every step of the way. You may be able to cancel or amend your Sleepy Hollow vacation package at no cost if you booked in the last 24 hours. But you may incur a fee from your hotel, airline or car rental company for older bookings. If your travel plans unexpectedly change, have a look at our [Customer Service Portal](https://www.expedia.ca/service/?langid=4105) for more information. ### Discover the most popular places to visit in Sleepy Hollow ![Wrigley Field featuring central business district, a city and a sporting event](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/35000/35620-Wrigley-Field.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wrigley Field 4.5/5(158 reviews) Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium. [](https://expedia.ca/Wrigley-Field-Lakeview.d6034754.Vacation-Attraction) ![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) ### Things to do ![Skydeck - Willis Tower Admission ](https://mediaim.expedia.com/localexpert/1342523/52299998-0f25-4483-b147-6aa89e72ca8e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Skydeck - Willis Tower Admission CA $62 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/skydeck-willis-tower-admission.a1342523.activity-details) ![Chicago: Navy Pier Centennial Wheel Regular & Express Ticket](https://mediaim.expedia.com/localexpert/4851853/9464687e-f5ac-4a15-9285-f6e26537484c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago: Navy Pier Centennial Wheel Ticket CA $35 per adult **84%** of travellers recommend [](https://expedia.ca/things-to-do/chicago-navy-pier-centennial-wheel-ticket.a4851853.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 $63 per adult **94%** of travellers recommend [](https://expedia.ca/things-to-do/wendellas-90-min-chicago-river-architecture-tour.a766175.activity-details) [See all activities in Chicago](https://expedia.ca/things-to-do/search?rid=6132427) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [Cheap Hotels in Archer Heights](https://www.expedia.ca/Archer-Heights-Chicago-Hotels-Cheap-Hotels.0-n6132347-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in Archer Heights](https://www.expedia.ca/Archer-Heights-Chicago-Hotels-Hotels-With-Free-Parking.0-n6132347-0-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Archer Heights](https://www.expedia.ca/Archer-Heights-Chicago-Hotels-Romantic-Hotel.0-n6132347-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Archer Heights Hotels](https://www.expedia.ca/Archer-Heights-Chicago-Hotels.0-n6132347-0.Travel-Guide-Filter-Hotels) - [Chicago Hotels](https://www.expedia.ca/Chicago-Hotels.d178248.Travel-Guide-Hotels) - [Downtown Chicago Hotels](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels.0-n6350699-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Garfield Ridge](https://www.expedia.ca/Garfield-Ridge-Chicago-Hotels-Cheap-Hotels.0-n6132357-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in Garfield Ridge](https://www.expedia.ca/Garfield-Ridge-Chicago-Hotels-Hotels-With-Free-Parking.0-n6132357-0-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Garfield Ridge](https://www.expedia.ca/Garfield-Ridge-Chicago-Hotels-Romantic-Hotel.0-n6132357-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Hotels near Midway Intl.](https://www.expedia.ca/Midway-Intl-Airport-Hotels.0-aMDW-0.Travel-Guide-Filter-Hotels) - [Hotels near Pulaski Station](https://www.expedia.ca/Pulaski-Station-Hotels.d6211019.Travel-Guide-Hotels) - [Flights to Chicago](https://www.expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights) - [Flights to Midway Intl.](https://www.expedia.ca/Cheap-Flights-To-Midway-Intl.d5719117.Travel-Guide-Flights) - [Flights from Midway Intl.](https://www.expedia.ca/lp/airports/mdw/flights-from-midway-intl-airport) - [Porter Airlines Toronto (YTZ) to Chicago (MDW) flights](https://www.expedia.ca/lp/flight-routes/porter-airlines-from-billy-bishop-toronto-city-to-midway-intl/pd/ytz/mdw) - [Porter Airlines Ottawa (YOW) to Chicago (MDW) flights](https://www.expedia.ca/lp/flight-routes/porter-airlines-from-macdonald-cartier-intl-to-midway-intl/pd/yow/mdw) - [Porter Airlines Montreal (YUL) to Chicago (MDW) flights](https://www.expedia.ca/lp/flight-routes/porter-airlines-from-pierre-elliott-trudeau-intl-to-midway-intl/pd/yul/mdw) - [Porter Airlines Thunder Bay (YQT) to Chicago (MDW) flights](https://www.expedia.ca/lp/flight-routes/porter-airlines-from-thunder-bay-intl-to-midway-intl/pd/yqt/mdw) - [Flights from Lake Of The Ozarks (AIZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/aiz/mdw/lake-of-the-ozarks-to-chicago) - [Flights from Atlanta (ATL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/atl/mdw/atlanta-to-chicago) - [Flights from Aurora (AUZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/auz/mdw/aurora-to-chicago) - [Flights from Bellingham (BLI) to Chicago (MDW)](https://www.expedia.ca/lp/flights/bli/mdw/bellingham-to-chicago) - [Flights from Boston (BOS) to Chicago (MDW)](https://www.expedia.ca/lp/flights/bos/mdw/boston-to-chicago) - [Flights from Buffalo (BUF) to Chicago (MDW)](https://www.expedia.ca/lp/flights/buf/mdw/buffalo-to-chicago) - [Flights from Baltimore (BWI) to Chicago (MDW)](https://www.expedia.ca/lp/flights/bwi/mdw/baltimore-to-chicago) - [Flights from Sault Ste. Marie (CIU) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ciu/mdw/sault-ste-marie-to-chicago) - [Flights from Detroit (DTW) to Chicago (MDW)](https://www.expedia.ca/lp/flights/dtw/mdw/detroit-to-chicago) - [Flights from Newark Liberty Intl. Airport (EWR) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ewr/mdw/newark-liberty-intl-airport-to-chicago) - [Flights from Fishers Island (FID) to Chicago (MDW)](https://www.expedia.ca/lp/flights/fid/mdw/fishers-island-to-chicago) - [Flights from Niagara Falls (IAG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/iag/mdw/niagara-falls-to-chicago) - [Flights from Las Vegas (LAS) to Chicago (MDW)](https://www.expedia.ca/lp/flights/las/mdw/las-vegas-to-chicago) - [Flights from Orlando (MCO) to Chicago (MDW)](https://www.expedia.ca/lp/flights/mco/mdw/orlando-to-chicago) - [Flights from Michigan City (MGC) to Chicago (MDW)](https://www.expedia.ca/lp/flights/mgc/mdw/michigan-city-to-chicago) - [Flights from Minneapolis (MSP) to Chicago (MDW)](https://www.expedia.ca/lp/flights/msp/mdw/minneapolis-to-chicago) - [Flights from Ogdensburg (OGS) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ogs/mdw/ogdensburg-to-chicago) - [Flights from Ontario (ONT) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ont/mdw/ontario-to-chicago) - [Flights from Plattsburgh (PBG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/pbg/mdw/plattsburgh-to-chicago) - [Flights from Philadelphia (PHL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/phl/mdw/philadelphia-to-chicago) - [Flights from South Bend (SBN) to Chicago (MDW)](https://www.expedia.ca/lp/flights/sbn/mdw/south-bend-to-chicago) - [Flights from Seattle (SEA) to Chicago (MDW)](https://www.expedia.ca/lp/flights/sea/mdw/seattle-to-chicago) - [Flights from Brandon (YBR) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ybr/mdw/brandon-to-chicago) - [Flights from Edmonton (YEG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yeg/mdw/edmonton-to-chicago) - [Flights from Hamilton (YHM) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yhm/mdw/hamilton-to-chicago) - [Flights from Halifax (YHZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yhz/mdw/halifax-to-chicago) - [Flights from Kelowna (YLW) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ylw/mdw/kelowna-to-chicago) - [Flights from Ottawa (YOW) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yow/mdw/ottawa-to-chicago) - [Flights from Peterborough (YPQ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ypq/mdw/peterborough-to-chicago) - [Flights from Québec (YQB) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yqb/mdw/quebec-to-chicago) - [Flights from Windsor (YQG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yqg/mdw/windsor-to-chicago) - [Flights from Moncton (YQM) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yqm/mdw/moncton-to-chicago) - [Flights from Thunder Bay (YQT) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yqt/mdw/thunder-bay-to-chicago) - [Flights from Sudbury (YSB) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ysb/mdw/sudbury-to-chicago) - [Flights from Timmins (YTS) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yts/mdw/timmins-to-chicago) - [Flights from Toronto (YTZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ytz/mdw/toronto-to-chicago) - [Flights from Montreal (YUL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yul/mdw/montreal-to-chicago) - [Flights from Vancouver (YVR) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yvr/mdw/vancouver-to-chicago) - [Flights from Winnipeg (YWG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ywg/mdw/winnipeg-to-chicago) - [Flights from Saskatoon (YXE) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yxe/mdw/saskatoon-to-chicago) - [Flights from North Bay (YYB) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yyb/mdw/north-bay-to-chicago) - [Flights from Calgary (YYC) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yyc/mdw/calgary-to-chicago) - [Flights from Toronto (YYZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yyz/mdw/toronto-to-chicago) - [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago) - [Art Institute of Chicago](https://www.expedia.ca/Art-Institute-Of-Chicago-Downtown-Chicago.d6064021.Vacation-Attraction) - [Broadview Vacations](https://www.expedia.ca/Broadview.d7064.Destination-Travel-Guides) - [Buckingham Fountain](https://www.expedia.ca/Buckingham-Fountain-Downtown-Chicago.d6064027.Vacation-Attraction) - [Burbank Vacations](https://www.expedia.ca/Burbank.d183178.Destination-Travel-Guides) - [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) - [Chicago Riverwalk](https://www.expedia.ca/Chicago-Riverwalk-Downtown-Chicago.d553248621533116610.Vacation-Attraction) - [Chicago Theatre](https://www.expedia.ca/Chicago-Theatre-Downtown-Chicago.d6064049.Vacation-Attraction) - [Chicago Vacations](https://www.expedia.ca/Chicago.d178248.Destination-Travel-Guides) - [Clearing Vacations](https://www.expedia.ca/Clearing.d6132083.Destination-Travel-Guides) - [Cloud Gate](https://www.expedia.ca/Cloud-Gate-Downtown-Chicago.d6182888.Vacation-Attraction) - [Ernest Hemingway Museum and House](https://www.expedia.ca/Ernest-Hemingway-Museum-And-House-Chicago.d6241604.Vacation-Attraction) - [Frank Lloyd Wright Historic District](https://www.expedia.ca/Frank-Lloyd-Wright-Historic-District-Chicago.d553248634340947645.Vacation-Attraction) - [Garfield Park Conservatory](https://www.expedia.ca/Garfield-Park-Conservatory-East-Garfield-Park.d6182807.Vacation-Attraction) - [Grant Park](https://www.expedia.ca/Grant-Park-Downtown-Chicago.d507389.Vacation-Attraction) - [Hometown Vacations](https://www.expedia.ca/Hometown.d6132133.Destination-Travel-Guides) - [House of Blues Chicago](https://www.expedia.ca/House-Of-Blues-Chicago-Downtown-Chicago.d6227753.Vacation-Attraction) - [Loretto Hospital](https://www.expedia.ca/Loretto-Hospital-Austin.d553248635997986962.Vacation-Attraction) - [Marina City](https://www.expedia.ca/Marina-City-Downtown-Chicago.d553248621533116577.Vacation-Attraction) - [Millennium Park](https://www.expedia.ca/Millennium-Park-Downtown-Chicago.d6069201.Vacation-Attraction) - [Obama's House](https://www.expedia.ca/Obamas-House-Kenwood.d553248621533116333.Vacation-Attraction) - [Richard J. Daley Center](https://www.expedia.ca/Richard-J-Daley-Center-Downtown-Chicago.d6175173.Vacation-Attraction) - [River Forest Vacations](https://www.expedia.ca/River-Forest.d5986.Destination-Travel-Guides) - [Robie House](https://www.expedia.ca/Robie-House-Hyde-Park.d6064059.Vacation-Attraction) - [South Loop Vacations](https://www.expedia.ca/South-Loop.d6130108.Destination-Travel-Guides) - [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) - [Unity Temple](https://www.expedia.ca/Unity-Temple-Chicago.d6064079.Vacation-Attraction) - [Willis Tower](https://www.expedia.ca/Willis-Tower-Downtown-Chicago.d6064069.Vacation-Attraction) - [Ace Rental Cars in Midway Intl.](https://www.expedia.ca/Ace-Car-Rentals-In-Midway-Intl.d5719117-c2.Car-Rental-Guide-Suppliers) - [Budget Rental Cars in Midway Intl.](https://www.expedia.ca/Budget-Car-Rentals-In-Midway-Intl.d5719117-c39.Car-Rental-Guide-Suppliers) - [Rental cars Midway Intl. airport](https://www.expedia.ca/Car-Rentals-In-Midway-Intl.d5719117.Car-Rental-Guide) - [Dollar Rent A Car Rental Cars in Midway Intl.](https://www.expedia.ca/Dollar-Rent-A-Car-Car-Rentals-In-Midway-Intl.d5719117-c43.Car-Rental-Guide-Suppliers) - [Enterprise Rental Cars in Midway Intl.](https://www.expedia.ca/Enterprise-Car-Rentals-In-Midway-Intl.d5719117-c15.Car-Rental-Guide-Suppliers) - [Express Travel Group Rental Cars in Midway Intl.](https://www.expedia.ca/Express-Travel-Group-Car-Rentals-In-Midway-Intl.d5719117-c1124.Car-Rental-Guide-Suppliers) - [Hertz Rental Cars in Midway Intl.](https://www.expedia.ca/Hertz-Car-Rentals-In-Midway-Intl.d5719117-c40.Car-Rental-Guide-Suppliers) - [Van Car Rentals near Midway Intl.](https://www.expedia.ca/Van-Car-Rentals-In-Midway-Intl.d5719117-tVan.Car-Rental-Guide-Class) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.