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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

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Chicago flight + hotel packages - 5 night stay

Chicago flight + hotel packages - 6 - 7 night stay

2021 Chicago vacations

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.

How much are vacation packages to Chicago?

With a Travelocity vacation package, you can live it up in Chicago for a mere $140. Flights, tours and hotels — we've got it all. You'll make great savings just for combining your bookings. And with everything taken care of before you even go, you won't have to worry about a thing.

How long should my Chicago vacation be?

Many travelers pack their suitcase and kick back in Chicago for about 2 nights. That gives you an idea of time frames, but you're not bound by it. Whether you just stay for a couple of days to see the famous attractions or linger a while to uncover hidden treasures, an unforgettable journey awaits.

Where can I get the best vacation package deals for Chicago?

Travelocity can help you snag a great Chicago package deal. With 400 partner airlines and 665,000 properties across the globe, you're bound to be able to craft the perfect itinerary.

Why should I book my vacation bundle with Travelocity?

With top-notch service, 24/7 support and some of the most perfect getaways imaginable, you'll never roam alone. And if you find a better price, we'll match it. That's our Price Match Guarantee.

Can I save money on my car rental if I book it with my hotel or flight?

Bundling your flight, car and hotel into a Chicago vacation package is a great way to score better prices. Plus, having your own wheels gives you freedom to make your way to all those amazing sights you're hoping to see. Located 37 miles from Chicago, Six Flags Great America is one attraction that should have a place on your itinerary. Top up the tank and make a day trip of it.

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

That comes down to whether you want to save money or visit Chicago when it's in full swing. The quietest time to see this part of the world is . If you'd like to experience this destination at its peak, consider . Want to save your hard-earned money? The cheapest month is . typically has the highest prices.

Which airport is best for Chicago?

Chicago, IL (ORD-O'Hare Intl.) is one of the top airports for Chicago. It's around 16 miles northwest of the downtown area. Your other options are Chicago, IL (MDW-Midway Intl.) (9 miles away from central Chicago) and Romeoville, IL (LOT-Lewis University) (31 miles away from central Chicago).

What is there to do in Chicago?

While getting off the beaten track is no doubt rewarding, you really shouldn't miss the big-name attractions that make a destination famous. Wrigley Field and Millennium Park are just two of them in Chicago.

Where should I stay when visiting Chicago?

You'll hear visitors recommending Downtown Chicago. If you plan to kick-start your Chicago adventures here, check out the Congress Plaza Hotel (3.0 stars) and the Hyatt Regency Chicago (4.0 stars). Another fantastic neighborhood to stay in is Magnificent Mile. Sought-after hotels here include the Warwick Allerton - Chicago (4.0 stars) and The Westin Michigan Avenue Chicago (4.5 stars).



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
(28 Reviews)
This luxury hotel features a full-service spa and 2 restaurants. Traveling on business? Take advantage of the business center and free WiFi in public areas. A terrace, dry cleaning, and concierge services are also on offer.
$125
Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile

4.5 out of 5.0 20 E Chestnut St, Chicago, IL
4.7/5
(40 Reviews)
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 airport shuttle. Valet parking, a coffee shop, and a terrace are also offered.
$65
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5.0 1100 S Michigan Ave, Chicago, IL
4.1/5
(45 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.

Things to do in Chicago

See all 160 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.