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. ![Hotel Lincoln](https://images.trvl-media.com/lodging/1000000/30000/23400/23314/48b7272b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Lincoln Lincoln Park $435 per person Jun 9 - Jun 11 found 11 hours ago Roundtrip non-stop flight included Las Vegas (LAS) to Chicago (ORD) 7.8/10 Good! (1,084 reviews) Very convenient to my daughter’s condo! Staff is very welcoming! We had a great view! Reviewed on Apr 3, 2026 ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/28e8042f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago Save 100% on your flight $1,112 per person Jun 6 - Jun 9 found 1 day ago Roundtrip flight included Phoenix (PHX) to Chicago (ORD) 9.4/10 Exceptional! (1,140 reviews) Perfect location, stunning hotel! Reviewed on Apr 5, 2026 ![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/7aab5ae1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### LondonHouse Chicago, Curio Collection by Hilton Downtown Chicago Save 100% on your flight $785 per person May 6 - May 9 found 9 hours ago Roundtrip flight included Tampa (TPA) to Chicago (ORD) 9.4/10 Exceptional! (3,647 reviews) Clean room! The view was amazing Reviewed on Apr 6, 2026 ![Embassy Suites by Hilton Chicago Downtown Magnificent Mile](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/da498d1e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Embassy Suites by Hilton Chicago Downtown Magnificent Mile Downtown Chicago $930 per person Jun 6 - Jun 9 found 20 hours ago Roundtrip flight included San Juan (SJU) to Chicago (ORD) 8.2/10 Very Good! (2,828 reviews) Staff was friendly, welcoming and helpful. Room was ready promptly and was very clean and comfortable. Breakfast was great, and even though it was very busy during spring break, staff did a great job accommodating the crowd by constantly cleaning tables and refreshing food. My only marks against the stay are that the pool was closed one of the days, and the elevators were being worked on, so there was often a line and a wait to use them. But the staff warned us about it upon check-in, so that made it more bearable. Reviewed on Apr 5, 2026 ![Warwick Allerton - Chicago](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/34f4da65_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Warwick Allerton - Chicago Downtown Chicago $612 per person Jun 6 - Jun 8 found 1 day ago Roundtrip non-stop flight included Las Vegas (LAS) to Chicago (ORD) 8.6/10 Excellent! (3,032 reviews) A beautiful historic hotel...we very much enjoyed our stay there. Reviewed on Mar 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/2026-05-06/2026-05-13/?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/1000000/20000/14500/14447/29a217ee_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Ritz-Carlton, Chicago Downtown Chicago $1,122 per person May 6 - May 9 found 1 day ago Roundtrip flight included St. Louis (STL) to Chicago (ORD) 9.2/10 Wonderful! (1,000 reviews) Enjoyed a very comfortable stay. Reviewed on Mar 30, 2026 ![Four Seasons Hotel Chicago](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/e5b56b9e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Four Seasons Hotel Chicago Downtown Chicago $1,645 per person Jun 6 - Jun 9 found 20 hours ago Roundtrip flight included San Juan (SJU) to Chicago (ORD) 9.4/10 Exceptional! (1,001 reviews) Service was wonderful! Hotel is very well located close to shops, restaurants and coffee shops. Lots to see and do around and hotel itself is pure luxury. We had a wonderful stay! Reviewed on Mar 27, 2026 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/e294b3a4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago $1,170 per person May 6 - May 8 found 1 day ago Roundtrip flight included Salt Lake City (SLC) to Chicago (ORD) 9.8/10 Exceptional! (1,010 reviews) Excellent room and facilities. Helpfull staff and amazing locstion. Reviewed on Mar 27, 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/2026-05-06/2026-05-13/?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. ![DoubleTree by Hilton Chicago - Magnificent Mile](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/w5771h3835x0y5-963f61be_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### DoubleTree by Hilton Chicago - Magnificent Mile Downtown Chicago $701 per person Jun 9 - Jun 12 found 6 hours ago Roundtrip flight included New Orleans (MSY) to Chicago (ORD) 8.8/10 Excellent! (2,391 reviews) Great rooms. The beds were very comfortable and the buffet breakfast was one of the nicest I’ve had in a US hotel in a while. I do wish they would just make regular chocolate chip cookies though stop adding nuts. I really love the warm chocolate chip cookies from the Doubletree. Reviewed on Apr 4, 2026 ![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/7aab5ae1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### LondonHouse Chicago, Curio Collection by Hilton Downtown Chicago Save 100% on your flight $749 per person Jun 10 - Jun 13 found 1 day ago Roundtrip non-stop flight included Miami (MIA) to Chicago (ORD) 9.4/10 Exceptional! (3,647 reviews) Clean room! The view was amazing Reviewed on Apr 6, 2026 ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/28e8042f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago Save 100% on your flight $1,112 per person Jun 6 - Jun 9 found 1 day ago Roundtrip flight included Phoenix (PHX) to Chicago (ORD) 9.4/10 Exceptional! (1,140 reviews) Perfect location, stunning hotel! Reviewed on Apr 5, 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/2026-05-06/2026-05-13/?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 Chicago Downtown](https://images.trvl-media.com/lodging/1000000/30000/26800/26728/w4000h2662x0y0-b6434af4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel 55 Chicago Downtown Downtown Chicago Save 100% on your flight $449 per person May 9 - May 13 found 1 day ago Roundtrip flight included Dallas (DFW) to Chicago (ORD) 8.8/10 Excellent! (1,575 reviews) Great location. The deluxe studio with the little nook and couch is great for having more space. Staff is super friendly, bathroom is good, the hotel bar is great with happy hour from 4-6. Reviewed on Apr 5, 2026 ![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/7aab5ae1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### LondonHouse Chicago, Curio Collection by Hilton Downtown Chicago Save 100% on your flight $861 per person Jun 10 - Jun 14 found 1 day ago Roundtrip flight included Rochester (RST) to Chicago (ORD) 9.4/10 Exceptional! (3,647 reviews) Clean room! The view was amazing Reviewed on Apr 6, 2026 ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/24d28405_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Embassy Suites by Hilton Chicago Downtown River North Downtown Chicago Save 100% on your flight $863 per person Jun 11 - Jun 15 found 6 hours ago Roundtrip non-stop flight included Charlotte (CLT) to Chicago (ORD) 8.6/10 Excellent! (5,808 reviews) It was great. I just wish the food better. Reviewed on Apr 5, 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/2026-05-06/2026-05-13/?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/1000000/10000/8100/8079/9d783fbd_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! (2,358 reviews) The hotel main lobby is so beautiful! The pool was great and warm for the cold weather. Everything is walking distance. Reviewed on Apr 3, 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/bc1f3373_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Regency McCormick Place Chicago 2233 S Martin Luther King Dr Chicago IL - 17 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! (1,073 reviews) Place was nice as always. We always go for a convention. Room was newly renovated. Trhe bathroom light wouldnt stay on though. It was on a timer and if you were in the shower it would just click off and youd be lift in darkness. Staff was okay for the most part besides the bell hop. Husband tried ... Reviewed on Mar 30, 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/w3840h2559x0y3-c577bf94_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! (3,477 reviews) This hotel is great! Great location, great staff. Reviewed on Apr 3, 2026 [](https://expedia.com/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) [See all 5,610 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