Chicago Vacation Packages 2025 from $596

Chicago flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Viceroy Chicago

Downtown Chicago

Save 100% on your flight

per person

Feb 2 - Feb 7

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel features 2 restaurants and a gym. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and laundry facilities.

Waldorf Astoria Chicago

Downtown Chicago

Save 100% on your flight

per person

Feb 2 - Feb 7

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the gym and perks like a free area shuttle.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

per person

Mar 14 - Mar 17

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Chicago (ORD)

A full-service spa and A 24-hour gym are featured at this smoke-free aparthotel. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and perks like free WiFi.

Virgin Hotels Chicago

Downtown Chicago

Save 100% on your flight

per person

Mar 14 - Mar 17

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

A nightclub, a 24-hour gym, and a restaurant are all featured at this luxury 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 coffee shop.

Pendry Chicago

Downtown Chicago

per person

Feb 6 - Feb 10

found 1 day ago

Roundtrip non-stop flight included

Dallas (DAL) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

Top Chicago hotels deals

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$140

includes taxes & fees

$119 per night

Dec 24 - Dec 25

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

Free WiFi

Restaurant

River Hotel

75 East Wacker Drive, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$109

includes taxes & fees

$93 per night

Jan 21 - Jan 22, 2025

A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-in, express check-out, and dry cleaning are also on offer.

Pet friendly

Free WiFi

Hyatt Regency Chicago

151 East Wacker Dr, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$193

includes taxes & fees

$164 per night

Jan 10 - Jan 11, 2025

This eco-certified hotel's 4 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A terrace, a snack bar/deli, and express check-in are also on offer.

Free WiFi

Restaurant

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

350 West Wolf Point Plaza, Building 2, Chicago, IL

Free Cancellation

$130

includes taxes & fees

$111 per night

Jan 7 - Jan 8, 2025

This smoke-free hotel includes 2 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the 15 conference rooms, free WiFi in public areas, and express check-in. Self parking, express check-out, and a computer station are also offered.

Pool

Free WiFi

Eurostars Magnificent Mile

660 North State Street, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$110

includes taxes & fees

$94 per night

Jan 20 - Jan 21, 2025

A full-service spa and a gym are featured at this boutique hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a sauna on site, and a 24-hour front desk and express check-out are also provided.

Spa

Free WiFi

Hilton Chicago

720 S Michigan Ave, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$169

includes taxes & fees

$144 per night

Dec 28 - Dec 29

This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A bar/lounge, a 24-hour front desk, and a coffee shop are also provided.

Pool

Pet friendly

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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

Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Wrigley Field

4.5/5(2,128 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

McCormick Place

4.5/5(1,805 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

Frequently asked questions

How much are vacation packages to Chicago?

Get ready to be surprised — you can vacation in Chicago for as low as $596. At Travelocity, we save you money and hassle with our excellent vacation packages. With hotels, flights and tours all in one place, why wait any longer?

How long should my Chicago vacation be?

Typically, 2 nights is what most tourists book for their Chicago trip. That’s a good starting point, but there’s plenty more to discover if you allow yourself a little longer.

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

Picking up the best package deal to Chicago is a piece of cake with Travelocity. With 400 air carriers and 1,000,000 properties all over the world, you’re spoiled for choice when it comes to your hotels and flights.

Why should I purchase my Chicago vacation bundle via Travelocity?

Because you’ll never roam alone if you book with us, and we offer round-the-clock support and exceptional service to boot. Add to that our Price Match Guarantee and tons of destinations to pick from. It’s our job to make your daydreams a reality.

Can I save money on my Chicago car rental if I bundle it with hotels and flights?

Absolutely — combine your flight, car and hotel into a Chicago vacation package and you can save a tidy sum. With so much to see in Chicago, having your own wheels will make exploring a joy. Once you’ve buckled yourself in, hit the wide open road and cruise toward Six Flags Great America, a famous attraction roughly 35 mi from Chicago.

Which airport is best for Chicago?

O’Hare Intl. Airport (ORD) (16 mi away from downtown), Midway Intl. Airport (MDW) (9 mi away from central Chicago) and Lewis University Airport (LOT) (30 mi away from central Chicago) are the main hubs in Chicago.

What is there to do in Chicago?

While hopping off the tourist trail is rewarding, you really shouldn’t miss the popular sights that make a place famous. Wrigley Field and Six Flags Great America are a couple of them in Chicago.

Where should I stay when visiting Chicago?

If you’re after someplace comfortable to lay your head, have a look at the Congress Plaza Hotel. It’s the top choice for many visitors.

Where to stay in Chicago: Best areas for travelers

Downtown Chicago: Full of atmosphere and ambiance, this is a perfect match if you love being in the thick of the action. Choose a comfortable room at the theWit Chicago - a DoubleTree by Hilton Hotel, the Renaissance Chicago Downtown Hotel or the Cambria Hotel Chicago Loop - Theatre District. Then, you'll be ideally placed to discover this neighborhood's best attractions, like Navy Pier and Chicago Children's Museum.
Near North Side: You've got lots of options when it comes to welcoming places to stay in this neighborhood. To start with, look up the Waldorf Astoria Chicago, The Talbott Hotel and the FieldHouse Jones. You'll be able to jump out of bed and be at terrific attractions like Navy Pier soon after.
Lakeview: If the reason for your travels is to check off the major attractions, staying here is a wise choice. Make yourself comfortable at The Wheelhouse Hotel, the City Suites Hotel or the Best Western Plus Hawthorne Terrace Hotel. Of the area's many highlights, the crowd favorite is Wrigley Field.
West Town: If you're on the hunt for someplace to stay in this area, the Ruby Room , the Beautiful Modern Bright And Open West Town Single Family Home and The Robey are convenient options. Creative types in particular will enjoy this part of town, with Ukrainian Institute Of Modern Art and Chicago Center for the Performing Arts among the many sights available here.
The Loop: If you only have time to discover one attraction in this neighborhood, make a beeline for Millennium Park. Take in this well-known sight at your own pace and then head on back to the Palmer House a Hilton Hotel. The Congress Plaza Hotel and the Chicago Athletic Association also have everything you need for a pleasant stay.