Oak Brook Vacation Packages 2026 from $545

Oak Brook flight + hotel vacation packages

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

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$545

per person

Aug 20 - Aug 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

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

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$588

per person

Oct 3 - Oct 6

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$791

per person

Sep 23 - Sep 27

found 19 hours ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A restaurant, a 24-hour front desk, and laundry facilities are also provided.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$681

per person

Oct 3 - Oct 6

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Chicago (ORD)

This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$1,251

per person

Oct 9 - Oct 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Self parking, a coffee shop, and a terrace are also offered.

Top Oak Brook hotels deals

Hyatt Regency O'Hare Chicago

9300 Bryn Mawr Ave Rosemont IL

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$193 total

Aug 3 - Aug 4

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Self parking, a coffee shop, and limo/town car service are also offered.

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Free Cancellation

Reserve now, pay when you stay

$190 nightly

$226 total

Jul 19 - Jul 20

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. A lobby fireplace, luggage storage, and wedding services are also on offer.

Omni Chicago Hotel

676 N Michigan Ave Chicago IL

Free Cancellation

Reserve now, pay when you stay

$295 nightly

$351 total

Jul 26 - Jul 27

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. There's in-room fitness on site, and concierge services and wedding services are also offered.

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

Free Cancellation

Reserve now, pay when you stay

$229 nightly

$269 total

Aug 7 - Aug 8

Total with taxes and fees

This hotel features 2 restaurants, a bar/lounge, and A 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. You'll appreciate the area shuttle, valet parking, and coffee shop/cafe.

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Free Cancellation

Reserve now, pay when you stay

$210 nightly

$250 total

Aug 10 - Aug 11

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

Hotel Riu Plaza Chicago

150 East Ontario Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$222 nightly

$264 total

Aug 9 - Aug 10

Total with taxes and fees

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.

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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.

Stay near popular Oak Brook attractions

A golf course with a large tree in the foreground, a pond, and a clear sky.

Oak Brook Golf Course

8.2/10 (147 reviews)

Enjoy a round of golf in Oak Brook at Oak Brook Golf Course. Stroll along the riverfront or attend a sporting event in this family-friendly area.

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Frequently asked questions

How much are vacation packages to Oak Brook?

Prepare to be surprised — you could find yourself in Oak Brook for only $545. 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.