Oak Brook Vacations
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Oak Brook Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
$464
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
$804
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Room was very clean and spacious. Staff was very helpful when we had issues with wifi (which were resolved very fast) and issues with flight cancellations impacting our arrival. Great breakfast buffet, lots of options and convenient. Rooftop bar was beautiful! The location was perfect for walking around the city and for getting to the red line. Would definitely recommend!!
Reviewed on Aug 19, 2026
Swissotel - Chicago
Downtown Chicago
$874
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Level Chicago Fulton Market
Downtown Chicago
$997
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.
Reviewed on Aug 17, 2026
The Talbott, Autograph Collection
Downtown Chicago
$609
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Front desk manager agreed to change my date with on-line service from the next weekend to the current weekend, so I booked and checked in.
4 days later, the on-line booking co. Said the manager did not agree to release my reservation.
Unethical procedurers.
Reviewed on Aug 12, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
$843
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Loved the location. Was able to park in the parking ramp, leave the car, and walk to many, many places! Room was clean, view was excellent, and choices of food/snacks was endless!
Reviewed on Aug 18, 2026
Oak Brook Vacation Packages
Hoping to save both time and money on your upcoming holiday to Oak Brook? The AARP Travel Center Powered by Expedia® can help you do both. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Oak Brook perfect. With just a few clicks, you can select the best vacation package for you and your family. We have a fabulous list of flights and lodgings, and local endeavors to pick from.
Hotel Deals in Oak Brook
You can choose from around 5081 hotels. Whether you want to stay in the heart of the city or pick a spot that is near all the Oak Brook hot spots, we have plenty of options available.
From Oak Brook hotels with multiple pools and on-site restaurants, to boutique accommodations that add all the extra touches, you'll find a hotel here that will make your trip amazing. With AARP Travel Center's Oak Brook hotel packages, you not only get a great rate on your flight, but also a wonderful place to stay.
Things to do in Oak Brook
Oak Brook is the perfect spot when you want to a break from it all. With only around 8,091 people living here year-round, this hidden-gem is great for a quite vacation. With the city's thriving art scene and a rich past that is a beacon for history fans you may have a hard time fitting everything into one trip.
If you need more suggestions, then make sure to click on AARP's "Things to Do" page.
Package Your Oak Brook Vacation and Save
With so much going on in Oak Brook, you'll be wanting to plan your outings, not spending time to searching for the hotel with the lowest rate. AARP Travel Center allows you to easily book all you need, and save some cash on your vacation. You can plan your whole vacation, including things to do in Oak Brook from only one place. The hardest packing you'll have to do is for your suitcase. Book now and save!
Top Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
River Hotel
75 East Wacker Drive Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
Fairmont Chicago at Millennium Park
200 North Columbus Drive Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Hilton Chicago
720 S Michigan Ave Chicago IL
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
Holiday Inn Chicago Dwtn - The Mart by IHG
350 West Wolf Point Plaza, Building 2 Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Thu, Oct 1 - Thu, Oct 8
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$178
Roundtrip
found 23 hours ago
Tue, Sep 29 - Sat, Oct 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$195
Roundtrip
found 5 days ago
Tue, Sep 29 - Sat, Oct 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$195
Roundtrip
found 5 days ago
Tue, Sep 29 - Sat, Oct 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$195
Roundtrip
found 5 days ago
Tue, Aug 25 - Sat, Aug 29
LAX
Los Angeles Intl.
MDW
Midway Intl.
$297
Roundtrip
found 4 days ago
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All accommodation types in Oak Brook
More Types of Hotels
- Hotels with Bars in Oak Brook
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- Hotels with a Pool in Oak Brook
- Resorts & Hotels with Spas in Oak Brook
- Hotel with wifi in Oak Brook
- Hotels with Complimentary Breakfast in Oak Brook
- Hotels with an Indoor Pool in Oak Brook
- Luxury Hotels in Oak Brook
- Hotels with Balconies in Oak Brook
- Hotel with a Concierge in Oak Brook
- Hotels with Hot Tubs in Oak Brook
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- Hotels with Fireplaces in Oak Brook
- Hotels with Tennis Courts in Oak Brook