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Save up to $986 | Book Flight + Hotel at the same time^
Save up to $986 | Book Flight + Hotel at the same time^
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Save up to $986 | Book Flight + Hotel at the same time^

Chicago Flight + Hotel Packages

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Chicago Flight + Hotel Packages - 5 Night Stay

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Chicago Vacations

You’ve long known of Chicago’s reputation as the “The Windy City,” and now that you’re here, wise wanderer, walking amid the fountains, bike trails, and art installations of Lake Michigan’s waterfront, you’ve certainly found yourself blown away. As one of the most storied cities in the U.S., Chicago overflows with history and culture around every corner, and there’s no shortage of exciting adventures awaiting you here. And by choosing one of the Chicago vacations featured here on Travelocity, you can sink your teeth into the Chi-Town’s iconic deep-dish pizza, root for the World Series-winning Cubs, and shop along the Magnificent Mile.

Hotels in Chicago

Embarking on your first adventure in this one-of-a-kind city? Where you choose to stay makes a big difference when it comes to vacations in Chicago. To ensure you make the right choice, here are four hotels you’ll fall in love with:

  • Congress Plaza Hotel: Looking for a luxurious space to serve as home base while in Chicago? This is the place. Offering views of lush Grant Park, this iconic downtown hotel has been a presence in the city since 1893 and is just a quick walk from the Art Institute of Chicago. Choose from rooms with marble bathrooms, whirlpool tubs, and views of Lake Michigan. Fitness fanatics can workout in the on-site exercise room, while foodies can sample the offerings at the Congress Plaza’s own steakhouse or lounge. And if you need a trim before a night out on the town, there’s even a barbershop in the hotel.
  • Hyatt Regency Chicago: Located a brisk walk from Millennium Park and the Magnificent Mile, this luxurious conference hotel sports contemporary rooms with iPod docks, high-def TVs, and for-a-fee Wi-Fi. To live it up a little, upgrade to a lakeview club room that includes complimentary breakfast on weekdays, and small bites in an upscale lounge. Other on-site eateries include a steak-and-sushi restaurant and a trendy sports bar.
  • Wyndham Grand Chicago Riverfront: Situated just two miles from Millennium Park, the high-end, pet-friendly Wyndham Grand hotel invites you to spend your nights in their extravagant rooms that include hardwood accents and high-definition TVs among other amenities. You can optionally upgrade to a riverview room, or reserve a suite replete with separate living spaces and a soaking tub. In-room massages are available for an additional fee, but access to the on-site fitness center is free for all guests. And as far as food is concerned, there’s an American restaurant with a bar and in-room dining services.
  • The Palmer House Hilton: Showcasing an ornately painted lobby that complements the masterful creations found in the nearby Art Institute of Chicago, this iconic accommodation is a mere 2 miles from the McCormick Place convention center. When it comes time to fill your belly after a day of collecting swag, pay a visit to the Palmer House’s restaurant, or swing by their plush lounge. Additional offerings here include a fitness center, full-service spa, and a pool and sauna sheltered from the elements.

Major Attractions

Choose one of our vacation packages in Chicago based around the attractions or activities you’re most looking forward to. In Near South is the sprawling Museum Campus, which consists of three large museums. Stargaze at the Adler Planetarium, pay a visit to the infamous Sue the T-Rex at the Field Museum of Natural History, and finish the museum hop at the Shedd Aquarium. Architecture aficionados will be drawn to the gorgeous buildings found in the Loop, including the Fine Arts Building, The Reliance Building, and the Rookery. Use the city's popular public transportation system to get around, but if you want to explore beyond the city limits you may want to rent a car in Chicago.

Festivals and Events

Every year, the Chicago River is dyed green for St. Patrick's Day, which is celebrated with a parade the Saturday before the holiday. This popular event is only one item in a crammed calendar of city events. Head outdoors to listen to classical music during the 10-week Grant Park Music Festival or sip on favorite beers while discovering new ones at the Chicago Craft Beer Festival in July. Live music, food, and the arts are the focus of most of the festivals. Let the festivals guide you when you plan vacation package in Chicago, IL.

Travelocity makes it easy to find a cheap vacation in Chicago at any time of year. Take a look at our unbeatable Chicago package deals today, and you’ll be on the trip of your dreams in no time.


Guide to Exploring Chicago

Chicago FAQs

What currency is used in Chicago?

The U.S. dollar (USD) is the currency used in Chicago.

What is there to do in Chicago?

With tons of fun adventures to keep you on your toes, you’ll never be bored in this city. Here are some activities to get you started:

Where is the best place to stay in Chicago?


Located right in the heart of the downtown area, The Loop is one of the most popular neighborhoods. You’ll be within walking distance of many local and boutique stores, award-winning restaurants and major cultural institutions.

This is the place to stay if you appreciate fine art and design. It’s about a mile from the downtown area and is regarded as Chicago’s most fashionable neighborhood. The Magnificent Mile, Chicago’s premier commercial district, is a short walk away.

What is Chicago famous for?

Nicknamed the “Windy City,” here are just a few things Chicago is known for:

  • History
  • Architecture

Don’t miss Willis Tower, an iconic skyscraper that features spectacular views of the city and surrounds. The Art Institute of Chicago is also nearby; plan a visit to explore its fantastic collection of impressionist paintings and sculptures. Millennium Park and Lake Michigan are ideal for nature lovers.

Top Chicago Hotels Deals

Eurostars Magnificent Mile, previously Dana Hotel $117
Eurostars Magnificent Mile, previously Dana Hotel

Eurostars Magnificent Mile, previously Dana Hotel

660 North State Street, Chicago, IL
     
    4.5
    of 5, from 53 reviews
    4.0 out of 5.0 Stars

    A full-service spa, a fitness center, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the a rooftop terrace, bar/lounge, and laundry facilities.

    Wyndham Grand Chicago Riverfront $135
    Wyndham Grand Chicago Riverfront

    Wyndham Grand Chicago Riverfront

    71 E Wacker Dr, Chicago, IL
       
      4.3
      of 5, from 173 reviews
      4.0 out of 5.0 Stars

      This hotel features a restaurant, a 24-hour fitness center, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A computer station, dry cleaning, and luggage storage are also on offer.

      Hotel Essex Chicago $86
      Hotel Essex Chicago

      Hotel Essex Chicago

      800 S Michigan Ave, Chicago, IL
         
        4.2
        of 5, from 13 reviews
        4.0 out of 5.0 Stars

        This hotel features a restaurant, a 24-hour fitness center, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A coffee shop, dry cleaning, and luggage storage are also on offer.

        The Whitehall Hotel $94
        The Whitehall Hotel

        The Whitehall Hotel

        105 E Delaware Pl, Chicago, IL
           
          4.2
          of 5, from 111 reviews
          4.0 out of 5.0 Stars

          This boutique hotel features 2 restaurants, a bar/lounge, and a fitness center. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, express check-in, and a computer station are also offered.

          DoubleTree by Hilton Chicago - Magnificent Mile $104
          DoubleTree by Hilton Chicago - Magnificent Mile

          DoubleTree by Hilton Chicago - Magnificent Mile

          300 E Ohio St, Chicago, IL
             
            4.1
            of 5, from 192 reviews
            3.5 out of 5.0 Stars

            This hotel features a restaurant, an outdoor pool, and a poolside bar. Traveling on business? Take advantage of the business center and WiFi in public areas. You'll appreciate the fitness center, bar/lounge, and rooftop terrace.

            Congress Plaza Hotel $122
            Congress Plaza Hotel

            Congress Plaza Hotel

            520 South Michigan Avenue, Chicago, IL
               
              3.7
              of 5, from 93 reviews
              3.5 out of 5.0 Stars

              This smoke-free hotel's 2 restaurants, 2 bars/lounges, and fitness center are some of the featured amenities. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and express check-in are also offered.

              The St. Clair Hotel – Magnificent Mile $200
              The St. Clair Hotel – Magnificent Mile

              The St. Clair Hotel – Magnificent Mile

              162 East Ontario Street, Chicago, IL
                 
                3.5
                of 5, from 26 reviews
                2.5 out of 5.0 Stars

                This hotel features free WiFi in public areas, laundry facilities, and valet parking. Luggage storage is provided and the front desk is staffed around-the-clock.

                Inn of Chicago $74
                Inn of Chicago

                Inn of Chicago

                162 E Ohio St, Chicago, IL
                   
                  3.5
                  of 5, from 121 reviews
                  3.0 out of 5.0 Stars

                  This hotel features a fitness center and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and a terrace are also offered.

                  Things to do in Chicago

                  See all 178 things to do in Chicago

                  Top Flight Deals to Chicago

                  Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

                  ^Savings based on all package bookings made with Flight + Hotel on Travelocity.com from January 1, 2018 to December 31, 2018, as compared to the 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.

                  *Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.