Deals on vacations and trips to Chicago

Save when you book Chicago, IL package deals

Choose two or more items and save on your trip:

Chicago flight + hotel vacation packages

21c Museum Hotel Chicago
The Langham, Chicago
Chicago Athletic Association, a Hyatt Hotel
Aloft Chicago Downtown River North
Viceroy Chicago

Top Chicago hotels deals

Don't see what you're looking for?
See all available properties in Chicago
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

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.

Tours and Activities in Chicago

So you've unpacked your suitcase and you're starting to feel weary after your flight — what do you do? Curl up in bed? Not a chance... getaways are about one-of-a-kind experiences and extraordinary adventures! (Besides, you can always have a rest when you get home.)

Looking forward to some thrilling activities while you're in Chicago? We recommend trying out some of these experiences:

Frequently asked questions

How much are vacation packages to Chicago?
You can find a great flight and hotel bundle from just $515. With one of our Travelocity vacation packages, a trip to Chicago has never looked so enticing! Save both time and money and then start packing that suitcase.
How long should my Chicago vacation be?
Around 2 nights is what many visitors book for their Chicago trip. That’s a great guide, but there’s so much more to uncover if you give yourself a little more time.
Where can I get the best vacation package deals for Chicago?
Travelocity has countless ways to score an awesome Chicago package deal. Select from 400 airlines and 1,000,000 properties across the globe and put together a vacation package that’s right for you. With so many options, it’s time to start planning your next great escape.
Why should I book my Chicago vacation package with Travelocity?
With our Price Match Guarantee, we’ll match any cheaper price you’re able to find. Add on our 24/7 customer support and first-rate service and your dream vacation is well within reach.
Will I save money on my Chicago car rental if I book it with my hotel or flight?
With a Chicago vacation package, you can bundle your flight, hotel and car bookings and save some serious money. If you want to see the best of this wonderful destination, why not check out Six Flags Great America? This renowned sight is 35 mi from Chicago. With your own set of wheels, you’ll be there belong long.
What is the best time of year to go to Chicago?
Consider visiting in if you don’t want to miss a thing. Even though they’re the busiest few months, the atmosphere of the tourist season is tough to resist. If you’d like a more leisurely pace, may suit you better. Don’t want to spend a packet on a place to stay? Shelve any plans to book in , when rates generally skyrocket. Look for someplace affordable in instead.
Which airport is best for Chicago?
O’Hare Intl. Airport (ORD) is popular. You’ll find it approximately 16 mi northwest of Chicago. Other options worth checking out are Midway Intl. Airport (MDW) (9 mi away from central Chicago) and Lewis University Airport (LOT) (30 mi away from central Chicago).
What is there to do in Chicago?
Chicago is full of sights to discover, like Wrigley Field and Millennium Park. These renowned attractions are at the top of most tourists’ must-see lists.
Where should I stay when visiting Chicago?
Many visitors spend their nights at the Congress Plaza Hotel. It’s an excellent base for your Chicago getaway.
Can I go on vacation to Chicago at this time?
Find out all the info that’s important relating to travel restrictions and quarantine policies ahead of your journey to Chicago. Our Covid-19 Travel Advisor is full of useful advice to help make your trip smooth and hassle-free.

Where to stay in Chicago: Best areas for travelers