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2021 Chicago vacations

Chicago vacation package deals

Chicago flight + hotel packages - 5-star hotels

Chicago flight + hotel packages - 4-star hotels

Chicago flight + hotel packages - 3-star hotels

Chicago flight + hotel packages - 2-star hotels

Chicago flight + hotel packages - 3 night stay

Chicago flight + hotel packages - 4 night stay

Chicago flight + hotel packages - 6 - 7 night stay

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:

Chicago FAQs

💥 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:

💥 When is the cheapest time to visit Chicago?

You will find the smallest crowds of tourists during September which generally reveals a cheaper time to book trips to Chicago.

💥 Where should I stay when visiting 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.

💥 When is high season in Chicago?

July and August are very popular times to take vacations to Chicago.

💥 What is Chicago known 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. 

💥 What is the best time of year to go to Chicago?

January is the best time to book Chicago vacation deals if you're looking for cheap travel rates.

💥 How affordable are activities in Chicago?

Travelers can find fun activities for as low as $6 which is very affordable in Chicago.

💥 What currency is used in Chicago?

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

Top Chicago Hotels Deals

$109
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5.0 85 East Wacker Drive, Chicago, IL
4.7/5
(27 Reviews)
A full-service spa, 2 restaurants, and a 24-hour fitness center are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A terrace, a free grocery shopping service, and a grocery/convenience store are also on offer.
$64
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5.0 1100 S Michigan Ave, Chicago, IL
4.2/5
(42 Reviews)
This hotel features a restaurant, a 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, express check-in, and dry cleaning are also on offer.
$90
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5.0 127 West Huron, at LaSalle, Chicago, IL
3.9/5
(16 Reviews)
This luxury hotel features a full-service spa, a nightclub, and 2 restaurants. Traveling on business? Take advantage of the 3 conference rooms, free WiFi in public areas, and valet parking. Make the most of the 24-hour fitness center and a rooftop terrace, and relax with drinks at one of the 2 bars/lounges.

Things to do in Chicago

See all 128 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, 2019 to December 31, 2019, 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.