Oak Brook Vacation Packages 2026 from $569

Oak Brook flight + hotel vacation packages

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

Fairmont Chicago at Millennium Park

Downtown Chicago

Save 100% on your flight

$569

per person

Jun 19 - Jun 22

found 21 hours ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities and in-room childcare. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$707

per person

Jun 5 - Jun 8

found 1 day ago

Roundtrip 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.

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$680

per person

Jun 5 - Jun 8

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.

Eurostars Magnificent Mile

Downtown Chicago

Save 100% on your flight

$759

per person

Jun 5 - Jun 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

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.

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$870

per person

Jun 19 - Jun 22

found 21 hours ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

A full-service spa, 2 restaurants, and a gym are all featured at this luxury hotel. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. A business center, a terrace, and dry cleaning are also on offer.

Top Oak Brook hotels deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$129 total

Apr 5 - Apr 6

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

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$140 total

Apr 12 - Apr 13

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-out, dry cleaning, and luggage storage are also on offer.

Pool

Pet friendly

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$153 total

Apr 12 - Apr 13

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free full breakfast each morning. Valet parking, a business center, and a grocery/convenience store are also offered.

Pool

Breakfast included

Hotel Riu Plaza Chicago

150 East Ontario Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$146 nightly

$172 total

Apr 5 - Apr 6

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.

Breakfast included

Free WiFi

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

Free Cancellation

Reserve now, pay when you stay

$221 nightly

$259 total

May 2 - May 3

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.

Free airport shuttle

Pet friendly

The Wade

644 N Lake Shore Dr Chicago IL

Free Cancellation

Reserve now, pay when you stay

$144 nightly

$169 total

Apr 27 - Apr 28

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and express check-out 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

Wrigley Field

4.5/5(2,149 reviews)

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

Naval Base Great Lakes

4.5/5(461 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

McCormick Place

4.5/5(1,830 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 Oak Brook?

Prepare to be surprised — you could find yourself in Oak Brook for only $569. 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.