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Downtown Chicago Vacation

Does Expedia have vacation package deals to Downtown Chicago?

Yes! Save by combining your lodgings and airfares. Expedia has plenty of outstanding Downtown Chicago vacation packages that'll simplify things and give you more money to splurge!

How much can I save with a Downtown Chicago vacation package?

Crafty travelers can save up to $583* by securing a package deal on Expedia.

Can I choose my airline with a Downtown Chicago Expedia vacation package?

Our extensive international database lists more than 750,000 properties worldwide and 550 partner airlines. With such a great range of options, organizing your dream vacation will be a breeze!

Do I lose money if I change my mind after I have booked my Downtown Chicago vacation package?

Not 100% sure about your booking? You won't pay us a cancellation fee if you make changes to almost any reservation.

What are the best places to visit in Downtown Chicago?

Preparing for your trip to Downtown Chicago? Keen for a few pointers about what to see when you're there? That's where we can help!

We couldn't envisage a better place to base yourself than Downtown Chicago. World-renowned attractions such as the Art Institute of Chicago and Willis Tower will be just moments away.

A jam-packed day of sightseeing can be tiring business. Fortunately, you won't have to travel far to get to Navy Pier and the Chicago Cultural Center. These nearby wonders will not disappoint!

If you're bored of dining indoors, grab some takeaway and enjoy a revitalizing lunch among the trees at Millennium Park. There's an excellent range of things to keep you busy in this destination. Those without a head for heights might want to look away, but anyone with a passion for skyscrapers shouldn't miss John Hancock Center. Reaching up towards the heavens, it's a stately fixture of the local area's skyline. Still got time to spare? Skydeck Ledge gives sightseers dazzling vistas as well as some impressive photo opportunities.

What are the Most popular activities for a Downtown Chicago vacation?

Life is either an extraordinary adventure or nothing at all, so why not throw yourself into some new and interesting experiences?

Kick off your trip to Downtown Chicago by trying a few of these activities:

If you'd rather take a look at a full list of activities, jump onto our Downtown Chicago things to do page.

What types of accommodations are available in Downtown Chicago?

Whatever kind of accommodations you're searching for, Downtown Chicago has you sorted. With 122 listed options to pick between, you'll be sure to find one that's perfect for your cheap vacation or luxury getaway.

If you're looking to save a few pennies, there are some excellent low-cost properties here, such as the Trump International Hotel & Tower Chicago (401 N Wabash Ave) and The St. Clair Hotel (162 East Ontario Street). When only the finest things in life will do, sleep in style at the Chicago Premier Suites (540 N State Street) or The Peninsula Chicago (108 East Superior Street). These luxurious retreats are also nearby.

Is being near the Art Institute of Chicago your chief priority? The Langham, Chicago and the JW Marriott Chicago are both within strolling distance.

Is there an airport in Downtown Chicago?

Getting on a plane to Midway International Airport (MDW)? It's situated 9 miles to the southwest of the middle of this neighborhood. Time to claim those bags and get your trip to Downtown Chicago rolling!



*Savings based on all vacation package bookings with Flight + Hotel on Expedia.ca from January through December 2020, as compared to price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.


Guide to Exploring around Downtown Chicago


Top Flight + Hotel Deals in Downtown Chicago

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

Best Lodging Options Near Downtown Chicago

See all 582 properties in Downtown Chicago
Eurostars Magnificent Mile, previously Dana Hotel CA $122
Reviewed on Jan. 18, 2020
See details
 
Eurostars Magnificent Mile, previously Dana Hotel

Eurostars Magnificent Mile, previously Dana Hotel

660 North State Street, Chicago, IL
     
    4.5 of 5
    4.0 out of 5.0 Stars

    Great location, very clean and modern, excellent service, and nice chic fun hotel. Quiet even with the cool rooftop bar.

    Warwick Allerton - Chicago CA $103
    Reviewed on Jan. 12, 2020
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    Warwick Allerton - Chicago

    Warwick Allerton - Chicago

    701 North Michigan Avenue, Chicago, IL
       
      4.1 of 5
      4.0 out of 5.0 Stars

      Friendly. Clean. Exceeded expectations fir the price. Perfect location

      Hyatt Regency Chicago CA $168
      Reviewed on Jan. 13, 2020
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      Hyatt Regency Chicago

      Hyatt Regency Chicago

      151 East Wacker Dr, Chicago, IL
         
        4.4 of 5
        4.0 out of 5.0 Stars

        I liked the beautiful views. The staff was very accommodating. The bell man greeted me at the door.

        Radisson Blu Aqua Hotel Chicago CA $165
        Reviewed on Jan. 11, 2020
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        Radisson Blu Aqua Hotel Chicago

        Radisson Blu Aqua Hotel Chicago

        221 N Columbus Dr, Chicago, IL
           
          4.5 of 5
          4.5 out of 5.0 Stars

          Really nice room, we had a corner room upgrade with a balcony, the view was nice. Bathroom had a shower and a deep soak tub.

          Palmer House a Hilton Hotel CA $121
          Reviewed on Jan. 13, 2020
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          Palmer House a Hilton Hotel

          Palmer House a Hilton Hotel

          17 E Monroe St, Chicago, IL
             
            4.2 of 5
            4.0 out of 5.0 Stars

            Hip and historic rooms have no coffee pot. Double beds are SMALL.

            Congress Plaza Hotel CA $103
            Reviewed on Jan. 11, 2020
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            Congress Plaza Hotel

            Congress Plaza Hotel

            520 South Michigan Avenue, Chicago, IL
               
              3.7 of 5
              3.5 out of 5.0 Stars

              Old hotel charm with modern amenities. Great location and staff was great

              Loews Chicago Hotel CA $151
              Reviewed on Jan. 17, 2020
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              Loews Chicago Hotel

              Loews Chicago Hotel

              455 North Park Drive, Chicago, IL
                 
                4.7 of 5
                4.5 out of 5.0 Stars

                The view was great! Very clean and the staff was very friendly

                River Hotel CA $92
                Reviewed on Jan. 17, 2020
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                River Hotel

                River Hotel

                75 East Wacker Drive, Chicago, IL
                   
                  4.2 of 5
                  4.0 out of 5.0 Stars

                  I love this place.. amazing location and fancy hotel

                  Top things to do in Downtown Chicago

                  See all 221 things to do in Downtown Chicago