Title: Hometown Vacation Packages & Trips 2025/2026 from CA $664 | Expedia.ca [Hotels in Hometown](https://expedia.ca/Hometown-Hotels.d6132133.Travel-Guide-Hotels)[Vacation Rentals in Hometown](https://expedia.ca/Hometown-Vacation-Rentals.d6132133.Travel-Guide-VacationRentals)[Hometown Car Rentals](https://expedia.ca/Car-Rentals-In-Hometown.d6132133.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) # Hometown 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 #### Your Hometown Vacation An easy way to experience this city is with a customized Hometown vacation package. Base yourself in the neighborhood of The Loop, which is great for bars and pubs, history and festivals or go someplace else — our package deals are all about you. Eager to venture out and explore? [SeatGeek Stadium](https://www.expedia.ca/SeatGeek-Stadium-Chicago.d6131157.Vacation-Attraction), [Chicago Ridge Shopping Mall](https://www.expedia.ca/Chicago-Ridge-Shopping-Mall-Chicago.d6143658.Vacation-Attraction) and [Trinity Christian College](https://www.expedia.ca/Trinity-Christian-College-Chicago.d6143660.Vacation-Attraction) are just a few of the most popular places to visit during your trip to Hometown. Browse Expedia's wide range of travel options and start organizing your ultimate vacation to Hometown today. ## Top Hometown Vacation Deals Price found within the past 48 hours. Click for updated prices. ![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 $664 per person Dec 4 - Dec 8 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,011 reviews) Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel Reviewed on Oct 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-08/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&dealMarker=vJpposegSqaEF0D5nI1Jf0uXYHffVlDJHFfneeYRy8MB8vE7ZX9oLnQQwYIXmd_e) ![The Westin Michigan Avenue Chicago](https://images.trvl-media.com/lodging/1000000/30000/21100/21055/dcfbf36b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Michigan Avenue Chicago Downtown Chicago CA $908 per person Dec 21 - Dec 25 found 13 hours ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 8.8/10 Excellent! (1,070 reviews) Excellent staff all around. I will return. Reviewed on Oct 25, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-21/2025-12-25/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21055&paandie=true&dealMarker=2iNwDrKkiFnmTHALAc1c6FC9bNsxEt539Z5hstTUuEwqIw1qmKV8LBuwibbcluGm) ![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 $799 per person Dec 4 - Dec 8 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,110 reviews) Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly. Reviewed on Oct 16, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-08/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=vJpposegSqaEF0D5nI1Jf0uXYHffVlDJHFfneeYRy8Okvds2LXufLuEBASMh_2Ml) ![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 $756 per person Jan 16 - Jan 19 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,761 reviews) The Trump never disappoints, always friendly, clean, and top notch service. We stay several times a year, they make you feel right at home. Reviewed on Oct 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-16/2026-01-19/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=vJpposegSqaEF0D5nI1Jf0SG8EhS4Lf8VtMYNxcMY8rUdpD5u5YQjX_imjQcoe-E) ![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 $747 per person Jan 15 - Jan 19 found 1 day ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9/10 Wonderful! (367 reviews) Easy check-in, friendly staff, beautiful building with nice amenities. Reviewed on Oct 27, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-15/2026-01-19/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&dealMarker=CaXpWBgXYeWbUJXqZnXmyhM2TacYJT6uOj_urWTWxlnW8tFxAz0y9YtuZeiflpEn) ## Ready to book your vacation to Hometown? Choose your dates ## Hometown Hotel Deals ![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 Fully refundableReserve now, pay when you stay CA $177 CA $208 total Nov 16 - Nov 17 includes taxes & fees 8.4/10 Very Good! (5,152 reviews) Clean room friendly staff Reviewed on Oct 26, 2025 [](https://expedia.ca/Hotel-Search?startDate=16%2F11%2F2025&endDate=17%2F11%2F2025&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=6132133) ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Congress Plaza Hotel 520 South Michigan Avenue, Chicago, IL Fully refundableReserve now, pay when you stay CA $131 CA $154 total Nov 24 - Nov 25 includes taxes & fees 7.8/10 Good! (9,592 reviews) From the moment we walked in the security was very friendly and helpful the first front desk attendant was amazing her name was Jasmine she was incredibly sweet helped us the best she could when we came back to do an early check-in the second person who helped us was incredibly rude service was terrible ... Reviewed on Oct 26, 2025 [](https://expedia.ca/Hotel-Search?startDate=24%2F11%2F2025&endDate=25%2F11%2F2025&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=6132133) ![Freehand Chicago](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Freehand Chicago 19 East Ohio Street, Chicago, IL Fully refundableReserve now, pay when you stay CA $95 CA $137 total Nov 26 - Nov 27 includes taxes & fees 7.8/10 Good! (2,508 reviews) Very accessible location and amazing staff. Reviewed on Oct 21, 2025 [](https://expedia.ca/Hotel-Search?startDate=26%2F11%2F2025&endDate=27%2F11%2F2025&selected=9418281&PinnedHotelID=9418281&HadPinnedHotel=true®ionId=6132133) [See all 4,511 properties in Hometown](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=28%2F10%2F2025&endDate=29%2F10%2F2025®ionId=6132133) 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 Hometown ![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 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 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) ### What to do in Hometown ![River tour boat in Chicago](https://mediaim.expedia.com/localexpert/170432/2ab44ef1-1211-4f4f-9436-ce9a14d4241f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Architecture River Tour CA $68 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/architecture-river-tour.a170432.activity-details) ![Relax and enjoy the view](https://mediaim.expedia.com/localexpert/46106377/6686561e-a3aa-4cbf-9e71-f553bde2fa06.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago Architecture Center River Cruise aboard First Lady CA $78 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/chicago-architecture-center-river-cruise-aboard-first-lady.a46106377.activity-details) ![Color Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/1b6e1be3-a6ba-4b3d-8e57-4d0336c3fd23.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Color Factory Chicago Ticket CA $47 per adult **94%** of travellers recommend [](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.activity-details) [See all activities in Hometown](https://expedia.ca/things-to-do/search?rid=6132133) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other ### Lodging - [3 Star Hotels in Chicago Ridge](https://www.expedia.ca/3Star-Chicago-Ridge-Hotels.s30-0-d89160.Travel-Guide-Filter-Hotels) - [Hotels near Advocate Christ Hospital and Medical Center](https://www.expedia.ca/Advocate-Christ-Hospital-And-Medical-Center-Hotels.0-l553248635997987068-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Ashburn](https://www.expedia.ca/Ashburn-Chicago-Hotels-Cheap-Hotels.0-n6132369-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Ashburn](https://www.expedia.ca/Ashburn-Chicago-Hotels-Hotel-With-Pool.0-n6132369-0-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Ashburn Hotels](https://www.expedia.ca/Ashburn-Chicago-Hotels.0-n6132369-0.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Beverly](https://www.expedia.ca/Beverly-Chicago-Hotels-Beach-Hotel.0-n6132394-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Beverly](https://www.expedia.ca/Beverly-Chicago-Hotels-Cheap-Hotels.0-n6132394-0-tCheapHotels.Travel-Guide-Filter-Hotels) - 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[Flights to Chicago](https://www.expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights) - [Flights from Oak Lawn](https://www.expedia.ca/lp/flights/9227/flights-from-oak-lawn) - [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago) ### Packages - [Art Institute of Chicago](https://www.expedia.ca/Art-Institute-Of-Chicago-Downtown-Chicago.d6064021.Vacation-Attraction) - [Blue Island Vacations](https://www.expedia.ca/Blue-Island.d80954.Destination-Travel-Guides) - [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) - [Chatham Fields Vacations](https://www.expedia.ca/Chatham-Fields.d6132323.Destination-Travel-Guides) - [Chicago Museum of Science and Industry](https://www.expedia.ca/Chicago-Museum-Of-Science-And-Industry-Hyde-Park.d6064043.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) - [Visit Cook County](https://www.expedia.ca/Cook-County.dx553248635083916453) - [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) - [Irondale Vacations](https://www.expedia.ca/Irondale.d6132291.Destination-Travel-Guides) - [Loretto Hospital](https://www.expedia.ca/Loretto-Hospital-Austin.d553248635997986962.Vacation-Attraction) - [Midlothian Vacations](https://www.expedia.ca/Midlothian.d133073.Destination-Travel-Guides) - [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) - [Phoenix Vacations](https://www.expedia.ca/Phoenix.d6132165.Destination-Travel-Guides) - [Richard J. Daley Center](https://www.expedia.ca/Richard-J-Daley-Center-Downtown-Chicago.d6175173.Vacation-Attraction) - [Robie House](https://www.expedia.ca/Robie-House-Hyde-Park.d6064059.Vacation-Attraction) - [Sleepy Hollow Vacations](https://www.expedia.ca/Sleepy-Hollow.d6132427.Destination-Travel-Guides) - [South Loop Vacations](https://www.expedia.ca/South-Loop.d6130108.Destination-Travel-Guides) - [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) ### Cars - [Budget Rental Cars in Oak Lawn](https://www.expedia.ca/Budget-Car-Rentals-In-Oak-Lawn.d9227-c39.Car-Rental-Guide-Suppliers) - [Car rental Burbank](https://www.expedia.ca/Car-Rentals-In-Burbank.d183178.Car-Rental-Guide) - [Car rental Chicago Ridge](https://www.expedia.ca/Car-Rentals-In-Chicago-Ridge.d89160.Car-Rental-Guide) - [Car rental Oak Lawn](https://www.expedia.ca/Car-Rentals-In-Oak-Lawn.d9227.Car-Rental-Guide) - [Europcar Rental Cars in Cook County](https://www.expedia.ca/Europcar-Destinations-In-Cook-County.d553248635083916453-c14.Car-Rental-Destination-Suppliers) - [Hertz Rental Cars in Oak Lawn](https://www.expedia.ca/Hertz-Car-Rentals-In-Oak-Lawn.d9227-c40.Car-Rental-Guide-Suppliers) - [Thrifty Car Rental Rental Cars in Oak Lawn](https://www.expedia.ca/Thrifty-Car-Rental-Car-Rentals-In-Oak-Lawn.d9227-c45.Car-Rental-Guide-Suppliers) ### Other - [Things to do in Oak Lawn](https://www.expedia.ca/Things-To-Do-In-Oak-Lawn.d9227.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. 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