Deals on vacations and trips to Chicago

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Chicago flight + hotel vacation packages

Pendry Chicago
Congress Plaza Hotel
Swissotel - Chicago
Fairmont Chicago at Millennium Park Gold Experience
LondonHouse Chicago, Curio Collection by Hilton
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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.

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?
Travelocity offers flight and hotel vacation packages starting as low as $419. With such huge savings, you’ll be exploring all of Chicago before too long.
How long should my Chicago vacation be?
An average of 2 nights is how long most visitors spend familiarizing themselves with the sights and sounds of Chicago. Wondering whether that’ll be enough time to tick everything off your itinerary? Stay another night or two so you don’t miss a thing.
Where can I get the best vacation package deals for Chicago?
It’s difficult to beat Travelocity when it comes to piecing together your Chicago package deal. There are as many as 400 air carriers and 1,000,000 worldwide properties to choose from. Book your trip now and get ready to tick another place off your travel bucket list.
Why should I book my Chicago vacation package via Travelocity?
Nothing beats the satisfaction of knowing you’ve bagged the best price available — that’s our Price Match Guarantee. Add to that our fantastic range of destinations and 24/7 team of customer service professionals and you’ve got the formula for a stress-free vacation.
Will I save money on my Chicago car rental if I bundle it with my hotel or flight?
Absolutely — combine your car, hotel and flight into a Chicago vacation package and you’ll save a ton. With so much to see and do in the Chicago area, having your own wheels will make it easy to explore. Once you’ve buckled yourself in, crank up the tunes and make tracks to Six Flags Great America, a renowned sight approximately 35 mi from Chicago.
What is the best time of year to go to Chicago?
If you really want to wander wisely, is the perfect time to do it. That’s when you’ll find hotel rates are at their cheapest. By way of comparison, prices skyrocket in . March, May and June are the most popular times to stay in Chicago, so expect long queues for tourist sights. Prefer to avoid the busy season? You’ll find more manageable crowds during December, January and February.
Which airport is best for Chicago?
O’Hare Intl. Airport (ORD) is 16 mi from the downtown area and is the beginning point for many fun adventures. Alternatively, Midway Intl. Airport (MDW) is 9 mi away from central Chicago and Lewis University Airport (LOT) is 30 mi away from central Chicago.
What is there to do in Chicago?
Chicago is teeming with places to discover, such as Wrigley Field and Six Flags Great America. These two impressive attractions top most visitors’ travel schedules.
Where should I stay when visiting Chicago?
The Congress Plaza Hotel is the number one choice of many visitors. Book soon to avoid missing out.

Where to stay in Chicago: Best areas for travelers