Title: Chicago Adventure Vacations 2026 | Expedia.com ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chicago Adventure Vacations ## Book a Adventure Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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 Adventure vacation packages in Chicago Price found within the past 48 hours. Click for updated prices. ![Warwick Allerton - Chicago](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Warwick Allerton - Chicago Downtown Chicago $241 per person Apr 14 - Apr 16 found 6 hours ago Roundtrip non-stop flight included Baltimore (BWI) to Chicago (ORD) 8.4/10 Very Good! (2,972 reviews) The staff was the best part, thank you Marcus! This made the stay, at this beautiful hotel. In a world that can seem disconnected, Marcus greeted us with a warm smile, a firm handshake, and gave us the lay of the land. His kind heart was welcoming and engaged. Finding amazing staff like this is hard to come by (coming from a a hospitality background). Our room was spotless and very comfortable. The common areas and hallways were clean and welcoming. I will recommend this hotel! Reviewed on Jan 23, 2026 ![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 $443 per person Mar 14 - Mar 16 found 10 hours ago Roundtrip flight included Dallas (DFW) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium. Reviewed on Jan 31, 2026 ![Sheraton Grand Chicago Riverwalk](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/4c0ebbe4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sheraton Grand Chicago Riverwalk Downtown Chicago Save 100% on your flight $588 per person Apr 16 - Apr 20 found 11 hours ago Roundtrip flight included Washington (WAS) to Chicago (ORD) 8.4/10 Very Good! (1,563 reviews) Great experience, great hotel! Clean, wonderful area as everything was walkable! Reviewed on Feb 2, 2026 ![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/74c2f40d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### LondonHouse Chicago, Curio Collection by Hilton Downtown Chicago $568 per person Mar 14 - Mar 16 found 10 hours ago Roundtrip flight included Dallas (DFW) to Chicago (ORD) 9.4/10 Exceptional! (3,392 reviews) I loved my stay at LondonHouse. I’ll definitely be staying at Curio Collection from now on. Reviewed on Feb 12, 2026 ![Hotel 55](https://images.trvl-media.com/lodging/1000000/30000/26800/26728/aa5efc6b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel 55 Downtown Chicago $304 per person Apr 14 - Apr 16 found 5 hours ago Roundtrip non-stop flight included Baltimore (BWI) to Chicago (ORD) 8.8/10 Excellent! (1,577 reviews) How clean everything was and great staff Reviewed on Feb 1, 2026 Don't see what you're looking for? See all available trips from Columbus to Chicago [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-12/2026-03-19/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Adventure vacations in Chicago Price found within the past 48 hours. Click for updated prices. ![The Ritz-Carlton, Chicago](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/30b68b68_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Ritz-Carlton, Chicago Downtown Chicago $596 per person Mar 14 - Mar 16 found 13 hours ago Roundtrip flight included New York (JFK) to Chicago (ORD) 9.2/10 Wonderful! (1,002 reviews) Great location, service, and gym Reviewed on Jan 24, 2026 ![Four Seasons Hotel Chicago](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/7da48e89_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Four Seasons Hotel Chicago Downtown Chicago Save 100% on your flight $921 per person Apr 16 - Apr 19 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (999 reviews) Room was great and staff very attebtive and kind Reviewed on Jan 20, 2026 ![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 $835 per person Apr 14 - Apr 16 found 4 hours ago Roundtrip flight included Buffalo (BUF) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Nice upgrade and amazing service Reviewed on Feb 9, 2026 Don't see what you're looking for? See all available trips from Columbus to Chicago [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-12/2026-03-19/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Adventure vacations in Chicago Price found within the past 48 hours. Click for updated prices. ![Warwick Allerton - Chicago](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Warwick Allerton - Chicago Downtown Chicago $364 per person Apr 14 - Apr 17 found 4 hours ago Roundtrip flight included Memphis (MEM) to Chicago (ORD) 8.4/10 Very Good! (2,972 reviews) The staff was the best part, thank you Marcus! This made the stay, at this beautiful hotel. In a world that can seem disconnected, Marcus greeted us with a warm smile, a firm handshake, and gave us the lay of the land. His kind heart was welcoming and engaged. Finding amazing staff like this is hard to come by (coming from a a hospitality background). Our room was spotless and very comfortable. The common areas and hallways were clean and welcoming. I will recommend this hotel! Reviewed on Jan 23, 2026 ![Hyatt Centric Chicago Magnificent Mile](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/w3837h2249x3y0-2724cf53_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Centric Chicago Magnificent Mile Downtown Chicago $519 per person Apr 14 - Apr 17 found 4 hours ago Roundtrip flight included Memphis (MEM) to Chicago (ORD) 9/10 Wonderful! (1,034 reviews) Connecting to Northwestern Hospital was the greatest thing ever Reviewed on Feb 11, 2026 ![Hotel 55](https://images.trvl-media.com/lodging/1000000/30000/26800/26728/aa5efc6b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel 55 Downtown Chicago $366 per person Apr 15 - Apr 18 found 14 hours ago Roundtrip flight included Orlando (MCO) to Chicago (ORD) 8.8/10 Excellent! (1,577 reviews) How clean everything was and great staff Reviewed on Feb 1, 2026 Don't see what you're looking for? See all available trips from Columbus to Chicago [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-12/2026-03-19/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Adventure vacations in Chicago Price found within the past 48 hours. Click for updated prices. ![Hotel 55](https://images.trvl-media.com/lodging/1000000/30000/26800/26728/aa5efc6b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel 55 Downtown Chicago Save 100% on your flight $481 per person Apr 16 - Apr 20 found 17 hours ago Roundtrip flight included Washington (WAS) to Chicago (ORD) 8.8/10 Excellent! (1,577 reviews) How clean everything was and great staff Reviewed on Feb 1, 2026 ![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/74c2f40d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### LondonHouse Chicago, Curio Collection by Hilton Downtown Chicago Save 100% on your flight $674 per person Apr 14 - Apr 18 found 12 hours ago Roundtrip flight included Los Angeles (LAX) to Chicago (ORD) 9.4/10 Exceptional! (3,392 reviews) I loved my stay at LondonHouse. I’ll definitely be staying at Curio Collection from now on. Reviewed on Feb 12, 2026 ![Hyatt Centric Chicago Magnificent Mile](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/w3837h2249x3y0-2724cf53_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Centric Chicago Magnificent Mile Downtown Chicago Save 100% on your flight $550 per person Apr 15 - Apr 19 found 4 hours ago Roundtrip flight included Fort Lauderdale (FLL) to Chicago (ORD) 9/10 Wonderful! (1,034 reviews) Connecting to Northwestern Hospital was the greatest thing ever Reviewed on Feb 11, 2026 Don't see what you're looking for? See all available trips from Columbus to Chicago [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-12/2026-03-19/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Find awesome Chicago adventure vacations #### How can I book the best Chicago adventure trips? Choose your own adventure in Chicago, whether that’s a white-knuckle experience or a weekend walk. Read the reviews of the adventures that have gone before to be sure your chosen stay is your idea of fun. #### How can I plan the perfect Chicago family adventure vacation? Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Chicago. Just make sure to check your chosen escapade is within the realms of can-do for the whole clan and will have the whole team grinning. #### Can I book all-inclusive Chicago adventure vacation packages? By refining your filters, you can explore all-amazing, all-adventurous, all-inclusive vacation packages. Amp up the extravagance with a few more filters too. Pick pristine pools, sensational spas, or wondrous waterparks for a sensational adventure getaway. #### Why should I book a Chicago adventure vacation for couples? Book a Chicago couples adventure vacation for the ultimate in romance and memory-making. Stunning scenery, heart-racing happenings, and the grandeur of the great outdoors—it’s the best way to bond. #### How can I find the best deals on adventure packages in Chicago? It’s easy to unleash fabulously affordable adventures. Enter the dates for your caper, then sort your search results by price or deals. #### Can I book an adventure vacation package in Chicago with free cancellation and/or flexible dates? Yes! When you’re searching for a great getaway, filter by payment option for free cancellation, so a change of plans won’t mess up your adventures. You’ll find buy now, pay later options, too, for full-on flexibility. #### Why should I book a Chicago adventure trip with Expedia? Adventure, airfare, accommodation, ATOL protection, and activities—all on one site. And that’s just the benefits that begin with A. ## Top Adventure Chicago Hotels ![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 - 12 min drive from Wrigley Field Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ... 8.6/10 Excellent! (2,290 reviews) Service, history, Reviewed on Feb 12, 2026 [](https://expedia.com/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Hyatt Regency McCormick Place Chicago ](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/64dd2430_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Regency McCormick Place Chicago 2233 S Martin Luther King Dr Chicago IL - 16 min drive from Wrigley Field Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ... 9.2/10 Wonderful! (1,068 reviews) Great place to stay Reviewed on Feb 10, 2026 [](https://expedia.com/Chicago-Hotels-Hyatt-Regency-McCormick-Place.h84736.Hotel-Information) ![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Regency Chicago 151 East Wacker Dr Chicago IL - 11 min drive from Wrigley Field Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ... 9.4/10 Exceptional! (3,471 reviews) Spacious and clean room but improvement points on amenities (missing tissue in tissue casing, need to call for amenities, nondairy milk available but not dairy milk, dirty coffee maker cannot make tea), dark, and separate towers inconvenient with friends & availability of lifts during conference ... Reviewed on Feb 10, 2026 [](https://expedia.com/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) [See all 5,628 properties in Chicago](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=178248) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. 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](https://expedia.com/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[ Chicago Hotels ](https://expedia.com/Chicago-Hotels.d178248.Travel-Guide-Hotels)[ Vacation Rentals in Chicago ](https://expedia.com/Chicago-Vacation-Rentals.d178248.Travel-Guide-VacationRentals)[ Car Rentals in Chicago ](https://expedia.com/Car-Rentals-In-Chicago.d178248.Car-Rental-Guide)[ Chicago Vacations ](https://expedia.com/Chicago.d178248.Destination-Travel-Guides)[ Things to do in Chicago ](https://expedia.com/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. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app