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Gross Point Vacations

Pack those stellar shades. We have Gross Point vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Gross Point – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Gross Point vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Gross Point

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Gross Point vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Gross Point well.

Top Hotel Deals

See all 639 Hotels in Gross Point
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago
    3.0 out of 5.0
     
     

    Built in 1893, this downtown Chicago hotel offers a convenient location across from Grant Park and close to Lake Michigan.

    Congress Plaza Hotel$149

    Congress Plaza Hotel$149
    Warwick Allerton - Chicago

    Warwick Allerton - Chicago

    701 North Michigan Avenue, Chicago
      4.0 out of 5.0
       
       

      Located on Michigan Avenue in the middle of Chicago's Magnificent Mile, this 1920s Italian Renaissance hotel is surrounded by fashionable shops, 1 mile from ...

      Warwick Allerton - Chicago$95

      Warwick Allerton - Chicago$95
      River Hotel

      River Hotel

      75 East Wacker Drive, Chicago
        4.0 out of 5.0
         
         

        Located in The Loop, this hotel is within a 10-minute walk of Chicago Theatre, Wrigley Building, and Tribune Tower. Ford Center for the Performing Arts Oriental ...

        River Hotel$93

        River Hotel$93
        Club Quarters Hotel, Central Loop

        Club Quarters Hotel, Central Loop

        111 West Adams Street, Chicago
          4.0 out of 5.0
           
           

          Club Quarters is a club-like hotel in the center of the Loop, Chicago’s central business district. A short walk to Symphony Center, the Art Institute, Board ...

          Club Quarters Hotel, Central Loop$93

          Club Quarters Hotel, Central Loop$93
          Kimpton Hotel Allegro

          Kimpton Hotel Allegro

          171 W Randolph St, Chicago
            4.0 out of 5.0
             
             

            Located in the Loop's theater district, Kimpton Hotel Allegro is next to the Cadillac Palace Theatre, 4 blocks from Millennium Park, and 1 mile from the Magnificent ...

            Kimpton Hotel Allegro$82

            Kimpton Hotel Allegro$82
            Hyatt Regency Chicago

            Hyatt Regency Chicago

            151 East Wacker Dr, Chicago
              4.0 out of 5.0
               
               

              This Magnificent Mile hotel is located among Chicago's world-class shopping, restaurants and attractions. The Navy Pier, Millennium Park and Art Institute are ...

              Hyatt Regency Chicago$89

              Hyatt Regency Chicago$89
              Best Western Grant Park Hotel

              Best Western Grant Park Hotel

              1100 S Michigan Ave, Chicago
                2.5 out of 5.0
                 
                 

                Favored for its location across from Grant Park, Museum Campus, Soldier Field, and Northerly Island, the Best Western Grant Park is also 1 mile from Millennium ...

                Best Western Grant Park Hotel$87

                Best Western Grant Park Hotel$87
                Edward Hotel Chicago

                Edward Hotel Chicago

                6600 N. Mannheim Rd, Rosemont
                  3.0 out of 5.0
                   
                   

                  Situated near the airport, this hotel is 0.4 mi (0.6 km) from Allstate Arena and within 3 mi (5 km) of Rivers Casino and Donald E. Stephens Convention Center. ...

                  Edward Hotel Chicago$89

                  Edward Hotel Chicago$89
                  Chicago's Essex Inn

                  Chicago's Essex Inn

                  800 S Michigan Ave, Chicago
                    3.5 out of 5.0
                     
                     

                    Across from the greenery and attractions of Grant Park, the Essex Inn is 3 blocks from the Loop business district and Lake Michigan, 4 blocks from the Art Institute, ...

                    Chicago's Essex Inn$79

                    Chicago's Essex Inn$79
                    Palmer House a Hilton Hotel

                    Palmer House a Hilton Hotel

                    17 E Monroe St, Chicago
                      4.0 out of 5.0
                       
                       

                      This 1925 Beaux Arts-style Chicago hotel is steps from Millennium Park, 2 blocks from Macy's and the Art Institute, and 1 mile from Lake Michigan, Magnificent ...

                      Palmer House a Hilton Hotel$105

                      Palmer House a Hilton Hotel$105

                      Top Flight Deals

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