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Featured Chicago Adventure Hotels

See all 1,166 Properties in Chicago
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

17 E Monroe St, Chicago
  • Free Cancellation
4.0 out of 5.0
 
 
4.2 out of 5 (10,758 reviews)
Weekend in ChicagoMuch to our surprise, the hotel worker's union in Chicago was on strike...so every time we went in and out, we passed the striker's line...which was uncomfortable. This led to few staff at check-in, and even fewer at the lounge Friday evening. We were glad to have checked in at 9:30 pm as we saw ...
Sep 17, 2018

$192 per night for 2 guests

Palmer House a Hilton Hotel$192
Hyatt Regency McCormick Place

Hyatt Regency McCormick Place

2233 S Martin Luther King Dr, Chicago
  • Free Cancellation
  • Reserve now, pay when you stay
4.0 out of 5.0
 
 
4.4 out of 5 (3,759 reviews)
I like the place except for when they ask you to put the Lot A parking on your room key for $36. It is $23 for 16 hours by just using the parking ticket and your credit card at the exit. The real problem is that the room key only works at one of the exits and that one is usually closed at night. ...
Sep 21, 2018

$179 per night for 2 guests

Hyatt Regency McCormick Place$179
Hyatt Regency Chicago

Hyatt Regency Chicago

151 East Wacker Dr, Chicago
  • Free Cancellation
  • Reserve now, pay when you stay
4.0 out of 5.0
 
 
4.4 out of 5 (9,805 reviews)
It was in the center of everything and everyone was very helpful
Sep 21, 2018

$222 per night for 2 guests

Hyatt Regency Chicago$222
Swissotel - Chicago

Swissotel - Chicago

323 E Wacker Dr, Chicago
    4.5 out of 5.0
     
     
    4.4 out of 5 (3,923 reviews)
    Quality hotel close to the Chicago centreGood modern location overlooking the park and the river.
    Sep 13, 2018

    $209 per night for 2 guests

    Swissotel - Chicago$209
    Hilton Chicago- Michigan Ave Cultural Mile

    Hilton Chicago- Michigan Ave Cultural Mile

    720 S Michigan Ave, Chicago
      4.0 out of 5.0
       
       
      4.2 out of 5 (4,995 reviews)
      Hilton Chicago Good location. Clean comfortable rooms. Easy check in.
      Sep 20, 2018
      Wyndham Grand Chicago Riverfront

      Wyndham Grand Chicago Riverfront

      71 E Wacker Dr, Chicago
        4.0 out of 5.0
         
         
        4.4 out of 5 (6,951 reviews)
        Excellent downtown hotel in Chicago Upgraded to suite so no complaints there. The only negative was that the room was difficult to heat. Very handy location, very friendly., attentive staff.
        Sep 14, 2018

        $167 per night for 2 guests

        Wyndham Grand Chicago Riverfront$167
        Radisson Blu Aqua Hotel Chicago

        Radisson Blu Aqua Hotel Chicago

        221 N Columbus Dr, Chicago
          4.5 out of 5.0
           
           
          4.5 out of 5 (1,626 reviews)
          Very well situated, concierge service very helpful for first time visitors, excellent
          Sep 17, 2018

          $260 per night for 2 guests

          Radisson Blu Aqua Hotel Chicago$260
          HI Chicago

          HI Chicago

          24 East Congress Parkway, Chicago
            1.5 out of 5.0
             
             
            4.3 out of 5 (1,210 reviews)
            convenient, cost effective & secureThis is the first Hostel my wife and I have very stayed in and we are aged mid to late 70's It is very convenient to the Blue Line to O'hare, Grant Park, the Hop On- Hop Off bus, eateries etc. It i very cost effective compared with Hotels, the included breakfast is great and security is tops.
            Sep 16, 2018

            $120 per night for 2 guests

            HI Chicago$120
            Hyatt Place Chicago/River North

            Hyatt Place Chicago/River North

            66 W Illinois St, Chicago
            • Free Cancellation
            • Reserve now, pay when you stay
            3.0 out of 5.0
             
             
            4.5 out of 5 (2,355 reviews)
            Short break in Chicago Location good for getting around & seeing Chicago sights, short walk to 2 subway lines and the Riverwalk. Bus stop across the road takes you to North Pier. Hotel room was spacious, very clean with fridge & coffee maker. Spacious bathroom as well. Staff were very helpful throughout my stay. Breakfast ...
            Sep 10, 2018

            $170 per night for 2 guests

            Hyatt Place Chicago/River North$170
            Hyatt Centric Chicago Magnificent Mile

            Hyatt Centric Chicago Magnificent Mile

            633 N Saint Clair St, Chicago
            • Free Cancellation
            • Reserve now, pay when you stay
            4.0 out of 5.0
             
             
            4.5 out of 5 (2,359 reviews)
            The hotel is a block from the magnificent mile and in walking distance to multiple stores, restaurants, and bars. Music venues and speakeasy bars are also very close. It is close to a hospital, but we slept very well and could only hear sirens at what seemed like a far distance
            Sep 13, 2018
            Sheraton Grand Chicago

            Sheraton Grand Chicago

            301 E North Water St, Chicago
            • Free Cancellation
            • Reserve now, pay when you stay
            4.0 out of 5.0
             
             
            4.2 out of 5 (4,264 reviews)
            Central to CityHotel workers on strike room cleaning removal of rubbish not up to satisfaction stayed four days and room not serviced even for the minimum amount. disappointing.
            Sep 17, 2018

            $249 per night for 2 guests

            Sheraton Grand Chicago$249
            Hotel Versey Days Inn by Wyndham Chicago

            Hotel Versey Days Inn by Wyndham Chicago

            644 West Diversey Parkway, Chicago
            • Free Cancellation
            • Reserve now, pay when you stay
            3.0 out of 5.0
             
             
            4.2 out of 5 (3,211 reviews)
            Liked its central location in Lincoln Park. Didn't like the fluctuating prices that changed over the time of our stay.
            Sep 15, 2018
            Club Quarters Hotel, Central Loop

            Club Quarters Hotel, Central Loop

            111 West Adams Street, Chicago
              4.0 out of 5.0
               
               
              4.3 out of 5 (6,163 reviews)
              Nice hotel, perfect centre loop location.Very nice hotel, the room we had was a little outdated and could do with freshening up. The only real negative point was there was no safe in the room which I’ve never come across in a hotel in Chicago. On the plus side the hotel provide free snacks, water, soft drinks and coffee. Despite the lack ...
              Sep 12, 2018

              $164 per night for 2 guests

              Club Quarters Hotel, Central Loop$164
              Silversmith Hotel Chicago Downtown

              Silversmith Hotel Chicago Downtown

              10 S Wabash Ave, Chicago
              • Free Cancellation
              • Reserve now, pay when you stay
              4.0 out of 5.0
               
               
              4.6 out of 5 (4,917 reviews)
              Great boutique hotel, spacious room. The only pitfalls I would mention: the sheets had a strong bleach aroma. I know hotels bleach their sheets but normally they don't smell so strong. And when I checked out, they mentioned the resort fee that needed to be charged, when questioned, she said this ...
              Sep 21, 2018

              $215 per night for 2 guests

              Silversmith Hotel Chicago Downtown$215
              Kinzie Hotel

              Kinzie Hotel

              20 W Kinzie St, Chicago
              • Free Cancellation
              • Reserve now, pay when you stay
              4.0 out of 5.0
               
               
              4.5 out of 5 (4,097 reviews)
              Had the cleanest carpet of any place we stayed on trip. Shower curtain a little short for staying inside tub
              Sep 21, 2018

              $199 per night for 2 guests

              Kinzie Hotel$199
              Warwick Allerton - Chicago

              Warwick Allerton - Chicago

              701 North Michigan Avenue, Chicago
              • Free Cancellation
              • Reserve now, pay when you stay
              4.0 out of 5.0
               
               
              4.1 out of 5 (9,247 reviews)
              Nice locale and beautiful hotel. Could use little updates here and there but generally great 👍
              Sep 21, 2018

              $134 per night for 2 guests

              Warwick Allerton - Chicago$134
              Chicago Athletic Association

              Chicago Athletic Association

              12 South Michigan Avenue, Chicago
                4.5 out of 5.0
                 
                 
                4.6 out of 5 (1,278 reviews)
                Bridget at front desk, extremely helpful, Cindy’s rooftop staff also very helpful for next day reservations, this is a landmark hotel in Chicago. Wonderful location on Michigan Avenue.
                Sep 15, 2018

                $229 per night for 2 guests

                Chicago Athletic Association$229
                Best Western Grant Park Hotel

                Best Western Grant Park Hotel

                1100 S Michigan Ave, Chicago
                • Free Cancellation
                • Reserve now, pay when you stay
                2.5 out of 5.0
                 
                 
                4.2 out of 5 (1,229 reviews)
                Nice hotel, good locationI have no major complaints about this hotel. It was comfortable and perfect for what we needed, which was somewhere to sleep in between seeing the sites during our first time in Chicago. We mostly hired the Divy bikes to get around, and there is plenty of bike racks close by. My one complaint would ...
                Sep 6, 2018

                $165 per night for 2 guests

                Best Western Grant Park Hotel$165
                The Buckingham Hotel

                The Buckingham Hotel

                425 S Financial Place, Chicago
                   
                   
                  4.3 out of 5 (725 reviews)
                  Love The BuckinghamI love the location, view, and hotel personnel. Deep in the loop or is close to the theater district and food. 5.5 mile walk to Wrigley was great fun.
                  May 28, 2018

                  $169 per night for 2 guests

                  The Buckingham Hotel$169
                  Embassy Suites Chicago Downtown

                  Embassy Suites Chicago Downtown

                  600 N State St, Chicago
                  • Free Cancellation
                  • Reserve now, pay when you stay
                  4.0 out of 5.0
                   
                   
                  4.4 out of 5 (3,624 reviews)
                  Great Hotel! Great Location!Great hotel within walking distance of shopping and restaurants. Checking in and out was a breeze. We arrived early, but was able to check-in anyway.
                  Aug 25, 2018

                  $169 per night for 2 guests

                  Embassy Suites Chicago Downtown$169
                  Map

                  Recently booked Adventure Hotels in Chicago

                  Best Western River North Hotel
                  3.0 out of 5.0
                  Last booking: 7 minutes ago
                  Hotel Chicago Downtown, Autograph Collection
                  4.0 out of 5.0
                  Last booking: 16 minutes ago
                  Hyatt Place Chicago/River North
                  3.0 out of 5.0
                  Last booking: 31 minutes ago
                  Heart O' Chicago
                  2.0 out of 5.0
                  Last booking: 33 minutes ago
                  Omni Chicago Suites - Magnificent Mile
                  4.5 out of 5.0
                  Last booking: 42 minutes ago
                  Baymont by Wyndham Mundelein Libertyville Area
                  2.5 out of 5.0
                  Last booking: 1 hour ago
                  Millennium Knickerbocker Chicago
                  4.0 out of 5.0
                  Last booking: 1 hour ago
                  Comfort Inn Arlington Heights - O'Hare
                  2.5 out of 5.0
                  Last booking: 1 hour ago
                  Baymont by Wyndham Chicago/Alsip
                  2.0 out of 5.0
                  Last booking: 2 hours ago

                  Chicago Adventure Hotel Guide

                  Chicago isn’t just for city slickers anymore. For those who love the great outdoors, there’s much to see and do in the Windy City. During warm weather, jet ski or leisurely paddleboard on Lake Michigan. Take in the scenery of the city by going on a hike through Lakeshore Path, or even book a Segway tour through Grant Park. After soaking up the natural beauty of this Illinois city, return to your comfortable Chicago adventure sport hotel. Nothing makes you appreciate nature’s beauty more than climbing into a soft bed after a long day of hiking.

                  At Expedia, we want to help you book a one-of-a-kind trip. We can even connect you to specialty boutique hotels in Chicago which fulfill your needs and fit your budget. We compile all the top Chicago hotel offers into one convenient location right here so you can have your pick. Whether you’re spending the day shopping at Magnificent Mile or inner-tubing in Lake Michigan, you can take a load off knowing you paid the best price possible on your adventure sport hotel.