Oak Brook Vacation Packages 2025/2026 from $322

Oak Brook flight + hotel vacation packages

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

Ameristar Casino Hotel East Chicago

Save 100% on your flight

$322

per person

Dec 24 - Dec 28

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Chicago (ORD)

This Art Deco hotel features a casino, a marina, and 5 restaurants. Enjoy the 24-hour gym and perks like free self parking. A bar/lounge, a 24-hour front desk, and a snack bar/deli are also provided.

Art Villa

West Town

Save 100% on your flight

$664

per person

Dec 31 - Jan 3

found 1 day ago

Roundtrip flight included

Dallas (DAL) to Chicago (ORD)

A full-service spa and a hot tub are featured at this luxury aparthotel. Enjoy the a rooftop terrace and perks like free self parking and a free airport shuttle. Free WiFi in public areas, a garden, and a lobby fireplace are also on offer.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$453

per person

Dec 31 - Jan 3

found 1 day ago

Roundtrip flight included

Dallas (DAL) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.

Waldorf Astoria Chicago

Downtown Chicago

Save 100% on your flight

$519

per person

Dec 24 - Dec 26

found 18 hours ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

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

Pendry Chicago

Downtown Chicago

Save 100% on your flight

$457

per person

Dec 31 - Jan 3

found 1 day ago

Roundtrip 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 Oak Brook hotels deals

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$116 nightly

$136 total

Nov 24 - Nov 25

Total with taxes and fees

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

Holiday Inn Chicago Dwtn - The Mart by IHG

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

Free Cancellation

$129 nightly

$152 total

Nov 24 - Nov 25

Total with taxes and fees

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. Enjoy the sauna and conveniences like a 24-hour front desk and laundry facilities.

Pool

Free WiFi

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$114 nightly

$134 total

Nov 16 - Nov 17

Total with taxes and fees

A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.

Pet friendly

Free WiFi

Freehand Chicago

19 East Ohio Street, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$84 nightly

$99 total

Nov 17 - Nov 18

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a coffee shop, and a snack bar/deli are also offered.

Pet friendly

Free WiFi

Palmer House a Hilton Hotel

17 E Monroe St, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$149 total

Nov 24 - Nov 25

Total with taxes and fees

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and limo/town car service.

Pool

Spa

citizenM Chicago Downtown

80 East Wacker Place, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$129 total

Oct 26 - Oct 27

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, a communal living room, and express check-in are also on offer.

Free WiFi

Restaurant

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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

Wrigley Field

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

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

Michigan Avenue

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.

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Frequently asked questions

How much are vacation packages to Oak Brook?

Prepare to be surprised — you could find yourself in Oak Brook for only $322. At Travelocity, we save you money and time with our vacation packages. With experiences, hotels and flights all ready to be snapped up, why wait?

How long should my Oak Brook vacation be?

Most sightseers vacation in Oak Brook for an average of 2 nights. That being said, traveling is all about finding new adventures and losing yourself in the moment — why not lock in a couple of additional nights so you can do just that?

Where can I get the best vacation package deals for Oak Brook?

Travelocity is the place to go to score a fantastic Oak Brook package deal. Take your pick of 400 air carriers and 1,000,000 properties all over the world and create a vacation package that's suited to you. With so many options, now's the time to book your next great escape.

Why should I book my Oak Brook vacation bundle via Travelocity?

From our 24/7 customer care to our range of exciting destinations, we're dedicated to giving you the most unforgettable vacation. All you need to do is click and book — our Price Match Guarantee will make sure you get the cheapest price.

Can I save money on my Oak Brook car rental if I combine it with my hotel or flight?

Certainly — bundle your car, flight and hotel into an Oak Brook vacation package and you'll save plenty. With so much to uncover in Oak Brook, having your own set of wheels will make exploring easy. Once you've buckled yourself in, turn up the tunes and head toward Six Flags Great America, a renowned sight approximately 35 mi from Oak Brook.

Which airport is best for Oak Brook?

It's highly likely you'll land at O'Hare Intl. Airport (ORD), which is 10 mi north of inner Oak Brook. Midway Intl. Airport (MDW) (12 mi away from central Oak Brook) and Lewis University Airport (LOT) (18 mi away from central Oak Brook) are other options.

What is there to do in Oak Brook?

Oak Brook has plenty of sights to explore, like Mayslake Peabody Mansion and Lizzadro Museum of Lapidary Art. These two popular attractions are on most tourists' travel itineraries.

Where should I stay when visiting Oak Brook?

The Hyatt House Chicago Oak Brook is the first choice of many travelers. Book soon before it's too late.