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It's time to fly. What's waiting for you in Harbor Square?

Perhaps you’re searching cheap flights to Harbor Square for a much-needed vacation or you simply have to roll in to see the relatives. Either way, we say rock that family reunion. Tell one too many stories at the hotel bar. Traveling for work? Crush it. If you lie back and relax without your cell phone, we won’t tell.

In the end you want to score a great deal and have a fantastic time, right? Flying is a small part of the whole adventure. We get that. Wherever you’re excited to go – or get away from – start this story with Hotwire’s cheap flights to Harbor Square.

Not sure how to get the best price on plane tickets to Harbor Square?

We know there are some airline aficionados out there. If you don’t know the industry like the back of your hand, don’t worry. You can make spending less look good with our booking tips.

Search certain days of the week for Harbor Square flights

For better savings, consider departing on a Wednesday, Thursday or Saturday. Return on a Sunday, Tuesday or Wednesday. International deals are often available when departing Monday through Thursday.

Change up your days for cheaper weekend getaways

Jetting off on Thursday and returning on Sunday is generally less expensive than flying on Friday and returning on Monday.

Stay a Saturday night to play more

Spending the weekend at your destination will generally result in lower airfares. We’re all for that.

Consider alternate airports when searching Harbor Square flights

Other nearby airports may offer different fares from your current search results. Clicking “Nearby Airports” after your initial search will give a list of the closest options.

See a fare that you like? Pounce!

Coordinate with your travel buddies before searching and you’ll be able to act quickly when it’s time to book. Airline ticket prices often change in minutes. We know you’re combing for the best prices but so is everyone else! If the deal is right, snag it and feel the sweet satisfaction of booking victory.

Fly during the off-peak season

Certain travel destinations have especially high volume during particular seasons. For example, Europe, Hawaii and Alaska are big hits in the summer. Florida, New Orleans and Southern California are the most popular in springtime. Winter is prime for Mexico and the Caribbean, as well as ski and snowboard destinations like the Colorado Rockies. In the autumn, Northern California, the Pacific Northwest and New England draw visitors. Flying during less popular periods can mean extra money in your wallet – yes, please!

Last Minute Hotel Deals in Harbor Square

See all 852 Properties in Harbor Square
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$103

    Palmer House a Hilton Hotel$103
    Congress Plaza Hotel

    Congress Plaza Hotel

    520 South Michigan Avenue, Chicago
      3.5 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$79

      Congress Plaza Hotel$79
      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$109

        Hyatt Regency Chicago$109
        Freehand Chicago

        Freehand Chicago

        19 East Ohio Street, Chicago
          3.5 out of 5.0
           
           

          Located in River North, this hotel is within a 10-minute walk of Chinese Consulate, Holy Name Cathedral, and Northwestern Memorial Hospital. Museum of Contemporary ...

          Freehand Chicago$60

          Freehand Chicago$60