Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5
Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.

Search over 1 million properties and 550 airlines worldwide

Search over 1 million flights, hotels, packages, and more

Free cancellation on most hotels. Because flexibility matters.


Does Expedia have holiday package deals to Chicago?

Yes! Expedia has some fantastic Chicago travel packages Combining your bookings is one of the simplest ways to save cash and time — and get your adventure off on the right foot.

How much can I save with a Chicago holiday package?

Smart jetsetters can save up to $583* by booking a package deal on Expedia.

Can I choose my airline with a Chicago Expedia holiday package?

Our enormous global database lists more than 750,000 properties worldwide and 550 partner airlines. With such a broad range of options, crafting your dream holiday will be easy!

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

Still undecided? There are no hidden fees from us if you change your mind for almost any reservation.

What are the best places to visit in Chicago?

Preparing for your trip to Chicago? Need some info about what to see when you arrive? That's where we can assist!

Take it from us, your bucket list will be heaps shorter after a trip to Chicago! Famed attractions like the Art Institute of Chicago and Willis Tower should be some of your first ports of call. The McCormick Place and the University of Illinois Chicago also draw in crowds of travellers from all across the globe.

You're going to find yourself surrounded by terrific things to do and see, including Navy Pier and the Lincoln Park Zoo. If you're dying to get the most out of your stay, also check out Lincoln Park and the Chicago Cultural Centre.

Millennium Park is an oasis amid the bustle of everyday life. Pull off your shoes and feel the cool grass beneath your feet or simply lie on your back and spot shapes in the clouds. Adventurers in this destination have heaps of options. Those who are a little queasy around heights might want to look away, but anyone who's curious about skyscrapers can't miss John Hancock Centre. Towering high above the ground, it's a beloved fixture of the area's skyline. Still have some time on your hands? Want to catch a sunrise among some spectacular scenery? Skydeck Ledge boasts glorious views that deserve to be photographed.

What are the most popular activities for a Chicago holiday?

When we hark back to our travels, we usually remember experiences rather than our swish hotel room and its view of the pool. Are you ready to create some new travel memories?

Your trip to Chicago is about to get a lot more exciting. There are heaps of activities available, such as:

To check out all the activities on offer, head to our Chicago things to do page.

What types of accommodation options are available in Chicago?

With no less than 165 accommodation in Chicago, finding a place to stay won't be difficult. But why wait around? Book now via Expedia and kick-start your next cheap holiday or luxury getaway.

Begin the quest for a dreamy Chicago base by looking into the latest offers at the Chicago Premier Suites (540 N State Street) and The Peninsula Chicago (108 East Superior Street). Alternatively, the Trump International Hotel & Tower Chicago (401 N Wabash Ave) and the Old Chicago Inn (3222 N Sheffield Ave) are two properties well worth investigating if you're travelling on the cheap.

If you'd rather stay nearby the Art Institute of Chicago, The Langham, Chicago and the JW Marriott Chicago are excellent options.

Is there an airport in Chicago?

We know the airport won't be the most memorable moment of your holiday, but there's nothing like the excitement of knowing that your well-deserved trip to Chicago is just a flight away! Once you unbuckle your seatbelt at Midway International Airport (MDW), you'll be 9 miles from the heart of town.




Guide to Exploring Chicago


Top Chicago Hotel & Accommodation Deals

See all 2,307 properties in Chicago
Warwick Allerton - Chicago
Reviewed on 19 Mar. 2020
See details
 
Warwick Allerton - Chicago

Warwick Allerton - Chicago

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

    This visit I received an upgrade to a beautiful room with a Michigan Ave view. It was lovely.

    The Whitehall Hotel NZ$136
    Reviewed on 21 Mar. 2020
    See details
     
    The Whitehall Hotel

    The Whitehall Hotel

    105 E Delaware Pl, Chicago, IL
       
      4.1 of 5
      4.0 out of 5.0 Stars

      I liked the vintage charm with a modern twist. It was a great location within walking distance of Michigan Avenue and all the stores.

      Swissotel - Chicago NZ$203
      Reviewed on 25 Mar. 2020
      See details
       
      Swissotel - Chicago

      Swissotel - Chicago

      323 E Wacker Dr, Chicago, IL
         
        4.4 of 5
        4.5 out of 5.0 Stars

        The "Urban Experience Fee" is a bit much. I mean, either add that amount into the room rate, make it optional or don't charge it. LOCATION is great! Staff attentive!

        Omni Chicago Suites - Magnificent Mile
        Reviewed on 24 Mar. 2020
        See details
         
        Omni Chicago Suites - Magnificent Mile

        Omni Chicago Suites - Magnificent Mile

        676 N Michigan Ave, Chicago, IL
           
          4.5 of 5
          4.5 out of 5.0 Stars

          It was very clean! Very comforting as well and we had a good stay.

          Royal Sonesta Chicago Riverfront
          Reviewed on 23 Mar. 2020
          See details
           
          Royal Sonesta Chicago Riverfront

          Royal Sonesta Chicago Riverfront

          71 E Wacker Dr, Chicago, IL
             
            4.3 of 5
            4.0 out of 5.0 Stars

            Everything was perfect! The staff is amazing. Stay in the Riverview rooms

            Congress Plaza Hotel NZ$135
            Reviewed on 21 Mar. 2020
            See details
             
            Congress Plaza Hotel

            Congress Plaza Hotel

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

              so beautiful and i could see the sears tower from my window

              The Godfrey Hotel Chicago NZ$167
              Reviewed on 26 Mar. 2020
              See details
               
              The Godfrey Hotel Chicago

              The Godfrey Hotel Chicago

              127 West Huron, at LaSalle, Chicago, IL
                 
                4.4 of 5
                4.5 out of 5.0 Stars

                No print out of my full bill no t very helpfull about my bill

                Edward Hotel Chicago NZ$112
                Reviewed on 21 Mar. 2020
                See details
                 
                Edward Hotel Chicago

                Edward Hotel Chicago

                6600 N. Mannheim Rd, Rosemont, IL
                   
                  4.0 of 5
                  3.0 out of 5.0 Stars

                  Everything was perfect.But the only problem was that the water from the pool was very cold.

                  Chicago 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.

                  Top 10 Things To Do In Chicago

                  See all 107 activities in Chicago