Oak Brook Vacations
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Oak Brook Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
$458
per person
Oct 26 - Oct 30
found 1 hour ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago Fulton Market
Downtown Chicago
$731
per person
Oct 26 - Oct 30
found 1 hour ago
Roundtrip flight included
Cleveland (CLE) 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.
Great staff and amenities. Beautiful pool, bbq area and more. Terrific room
Only issues was parking was $68 a day, plus incidental holds of $200 per day. Security is strong and is close to Fulton Market and we would walk over to the RiverWalk every day
As the hotel is permanent residents and renters security is job 1. Problems you have to go to the third floor to get a baggage cart and you have to leave your drivers license, which I didn’t care for and to get into the garage you have to call security and more than once no one answered and you had to go into the building and find them.
For the money your room key or a key pad should allow you in.
Reviewed on Aug 21, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
$654
per person
Oct 26 - Oct 30
found 1 hour ago
Roundtrip flight included
Cleveland (CLE) 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.
Level Chicago – Old Town
Downtown Chicago
$627
per person
Oct 26 - Oct 30
found 1 hour ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
$494
per person
Oct 26 - Oct 30
found 1 hour ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)
Stay at this 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.
The location could not be better--close to Michigan Avenue and the Red Line L--and the property is clean, quiet, and safe. The only thing that rankled were the elevators, for which one typically has to wait years for: ended up taking the stairs often, and I was staying on the 9th floor.
Reviewed on Aug 21, 2026
River Hotel
Downtown Chicago
$462
per person
Oct 26 - Oct 30
found 1 hour ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)
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 rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The location was perfect, and the staff was extremely helpful
Reviewed on Aug 22, 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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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.
Wed, Oct 21 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$148
Roundtrip
found 2 days ago
Tue, Oct 13 - Tue, Oct 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$173
Roundtrip
found 2 days ago
Thu, Oct 1 - Mon, Oct 5
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197
Roundtrip
found 2 days ago
Tue, Sep 29 - Tue, Oct 6
LAX
Los Angeles Intl.
MDW
Midway Intl.
$197
Roundtrip
found 9 hours ago
Thu, Oct 1 - Mon, Oct 5
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217
Roundtrip
found 2 days ago
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All accommodation types in Oak Brook
More Types of Hotels
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