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. ![Chicago Athletic Association, a Hyatt Hotel](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118328/6b24bc12_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Chicago Athletic Association, a Hyatt Hotel Downtown Chicago Save 100% on your flight $487 per person Apr 13 - Apr 16 found 20 hours ago Roundtrip non-stop flight included Washington (WAS) to Chicago (ORD) 9/10 Wonderful! (1,002 reviews) Joyce and Jean really made my stay at the Chicago Athletic Association one of the most stellar experiences I’ve ever had. They both went above and beyond to make sure I had whatever I needed and the attentiveness for the staff at large was impeccable. Check-in was a breeze and from there the accommodations were top-tier. The room was wonderfully appointed, and the hotel amenities could not be beaten. I will always come back to this hotel. Reviewed on Jan 5, 2026 ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Palmer House a Hilton Hotel Downtown Chicago Save 100% on your flight $966 per person Apr 13 - Apr 18 found 22 hours ago Roundtrip flight included San Juan (SJU) to Chicago (ORD) 8.4/10 Very Good! (2,059 reviews) Clean room, nice size. Housekeeping staff in particular were very nice and helpful. No coffee maker in the room, hence 4 vs 5 stars. Reviewed on Feb 10, 2026 ![Kinzie Hotel](https://images.trvl-media.com/lodging/1000000/1000000/992500/992500/6044b661_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kinzie Hotel Downtown Chicago $638 per person Apr 13 - Apr 18 found 22 hours ago Roundtrip flight included San Juan (SJU) to Chicago (ORD) 9.2/10 Wonderful! (1,993 reviews) The room was incredibly clean and had a great view! The staff was so nice and Deandre was such a wonderful host at checkout. Thank you for the amazing stay! Reviewed on Jan 29, 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 $667 per person Apr 13 - Apr 17 found 1 day ago Roundtrip flight included Tampa (TPA) to Chicago (ORD) 9/10 Wonderful! (1,034 reviews) All good. bar staff was not that friendlly Reviewed on Feb 3, 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 Save 100% on your flight $559 per person Mar 13 - Mar 15 found 1 day ago Roundtrip flight included Atlanta (ATL) 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 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/2026-03-11/2026-03-18/?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 $638 per person Mar 13 - Mar 15 found 1 day ago Roundtrip flight included Atlanta (ATL) 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 16 hours 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 $837 per person Apr 13 - Apr 15 found 1 day ago Roundtrip flight included Washington (WAS) 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/2026-03-11/2026-03-18/?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 Save 100% on your flight $240 per person Apr 13 - Apr 16 found 1 day ago Roundtrip flight included Atlanta (ATL) 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 ![The Royal Sonesta Chicago River North](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/20c3f16a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Royal Sonesta Chicago River North Downtown Chicago Save 100% on your flight $279 per person Apr 13 - Apr 16 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.2/10 Wonderful! (2,241 reviews) Clean great staff they let us store our luggage after check out until our flight. Reviewed on Feb 7, 2026 ![The Royal Sonesta Chicago Downtown](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Royal Sonesta Chicago Downtown Downtown Chicago Save 100% on your flight $320 per person Apr 13 - Apr 16 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (3,062 reviews) Clean room and great staff! Reviewed on Feb 10, 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/2026-03-11/2026-03-18/?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. ![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 $310 per person Apr 13 - Apr 17 found 4 hours ago Roundtrip flight included Dallas (DFW) 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 ![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 $624 per person Apr 13 - Apr 17 found 4 hours ago Roundtrip flight included Dallas (DFW) to Chicago (ORD) 9.4/10 Exceptional! (3,392 reviews) Clean rooms, great reception, and beautiful views! Reviewed on Feb 10, 2026 ![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Regency Chicago Downtown Chicago Save 100% on your flight $846 per person Apr 14 - Apr 18 found 1 day ago Roundtrip non-stop flight included Washington (WAS) to Chicago (ORD) 9.4/10 Exceptional! (3,386 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 season low. Road works and access by car/cab not warned Reviewed on Feb 10, 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/2026-03-11/2026-03-18/?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 ... 8.4/10 Very Good! (2,278 reviews) Hotel and staff was great. Great location. Just wish more elevators worked because it was a huge audition festival and elevator situation was dire. Reviewed on Feb 6, 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 ... 9/10 Wonderful! (1,065 reviews) Very nice Hotel. Nice room and view!! The staff were friendly. We will be back to stay at this Hotel. Reviewed on Jan 31, 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 ... 9.2/10 Wonderful! (3,468 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 5,624 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. Additional terms may apply. ## More vacations you might like ![](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.com/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.com/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) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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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