Oak Brook Holidays
Photo by Judy Mahoney
- Plan, book, travel with confidence
- Better togetherSave up to S$134 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Oak Brook Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Grand Royal Hotel O'Hare - Chicago
Price was S$907, price is now S$691 per person
S$691
per person
28 Mar - 4 Apr
found 1 day ago
Return direct flight included
Syracuse (SYR) to Chicago (ORD)
5.8/10 (215 reviews)
Friendly front desk, easy and convenient for my overnight layover in Chicago
Reviewed on 7 Nov, 2025
Hilton Chicago O'Hare Airport
O'Hare
Save 100% on your flight
Price was S$2,021, price is now S$1,404 per person
S$1,404
per person
28 Mar - 4 Apr
found 1 day ago
Return direct flight included
Syracuse (SYR) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Great stay fir early flights
Reviewed on 8 Jan, 2026
Hilton Rosemont Chicago O'Hare
Price was S$1,516, price is now S$1,165 per person
S$1,165
per person
28 Mar - 4 Apr
found 1 day ago
Return direct flight included
Syracuse (SYR) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
The room and staff were extremely friendly, but I specifically requested a room with a bath so I could soak my leg after a surgery. There was absolutely no water pressure when it came to the bath and the drain wouldn't close all the way. For how much I paid I feel like I should have been able to take a bath
Reviewed on 8 Dec, 2025
DoubleTree by Hilton Chicago - Oak Brook
Price was S$1,245, price is now S$957 per person
S$957
per person
28 Mar - 4 Apr
found 1 day ago
Return direct flight included
Syracuse (SYR) to Chicago (ORD)
6.8/10 (1,000 reviews)
Hotel is old and showing its age.
Rooms are old too. Few amenities etc.
Reviewed on 6 Jan, 2026
Top hotels in Oak Brook
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$247 per night from 18 Jan to 19 Jan
S$247
18 Jan - 19 Jan
includes taxes & fees
8.4/10 Very Good! (2,501 reviews)
Everything was amazing abt my stay
Reviewed on 7 Jan, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$135 per night from 18 Jan to 19 Jan
S$135
18 Jan - 19 Jan
includes taxes & fees
8.8/10 Excellent! (3,678 reviews)
Room and hotel overall very clean. Noted some things that could be updated in bathroom(stopper in sink didnt go all the way down, peeling caulk and some missing grout). Minor updates. Our sink was clogged when we checked in and I called the front desk, housekeeping and the hotel hotline 4 different ...
Reviewed on 7 Jan, 2026
Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$126 per night from 12 Jan to 13 Jan
S$126
12 Jan - 13 Jan
includes taxes & fees
8.6/10 Excellent! (2,051 reviews)
Great location & everyone was very helpful. Needed a fridge for medication & they set us up in a room with one.
Reviewed on 8 Jan, 2026
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
Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.
McCormick Place
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.
Soldier Field
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
What to do in Oak Brook
Skydeck - Willis Tower Admission
S$57
per adult
100% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
S$32
per adult
88% of travellers recommend
Explore a world of travel with Expedia
- 4 Star Hotels in Forest View
- Hotels with Swimming Pools in Addison
- Addison Hotels
- Motel 6 Hotels in Bellwood
- Berkeley Hotels
- Broadview Hotels
- Burr Ridge Hotels
- Clarendon Hills Hotels
- Hotels with Entertainment in Countryside
- Countryside Hotels
- Darien Hotels
- Downers Grove Hotels
- Hotels with kitchenette in Elmhurst
- Elmhurst Hotels
- Apartments in Forest View
- Hotels near Galloping Ghost
- Glen Ellyn Hotels
- Hillside Hotels
- La Grange Hotels
- Lisle Hotels
- Apartments in Lombard
- Hotels with Swimming Pools in Lombard
- Lombard Hotels
- Maywood Hotels
- Apartments in Melrose Park
- Condo Rentals in Melrose Park Bellwood Station
- Fairmont Hotels in Melrose Park
- Melrose Park Hotels
- North Riverside Hotels
- Oak Brook Hotels
- River Forest Hotels
- Riverside Hotels
- Stone Park Hotels
- Summit Hotels
- Western Springs Hotels
- Condo Rentals in Westmont
- Westmont Hotels
- Willowbrook Hotels
- Woodridge Hotels
- Flights to Berkeley
- Flights to Hillside
- Flights to Indian Head Park
- Flights to Lombard
- Flights to Melrose Park
- Flights from Franklin Park
- Flights from Downers Grove
- Flights from Lombard
- Flights from Guangzhou (CAN) to Chicago (ORD)
- Flights from Jakarta (CGK) to Chicago (ORD)
- Flights from Coimbatore (CJB) to Chicago (ORD)
- Flights from Colorado Springs (COS) to Chicago (ORD)
- Flights from Dhaka (DAC) to Chicago (ORD)
- Flights from Evanston (EVW) to Chicago (ORD)
- Flights from Houston (HOU) to Chicago (ORD)
- Flights from Kuala Lumpur (KUL) to Chicago (ORD)
- Flights from Lima (LIM) to Chicago (ORD)
- Flights from Mendoza (MDZ) to Chicago (ORD)
- Flights from Düsseldorf (MGL) to Chicago (ORD)
- Flights from Manhattan (MHK) to Chicago (ORD)
- Flights from Madison (MSN) to Chicago (ORD)
- Flights from Perth (PER) to Chicago (ORD)
- Flights from St. Louis (STL) to Chicago (ORD)
- Flights from Twentynine Palms (TNP) to Chicago (ORD)
- Flights from Tampa (TPA) to Chicago (ORD)
- Aon Center
- Apollo Theater Chicago
- Visit Bellwood
- Centennial Beach
- Centennial Park Aquatic Center
- Cicero Holidays
- Countryside Holidays
- Downers Grove Holidays
- Elmhurst Holidays
- Frank Lloyd Wright Historic District
- Goose Island Holidays
- Lakeview Holidays
- Legoland® Discovery Center
- Visit Lombard
- Melrose Park Holidays
- Visit Melrose Park
- Morton Arboretum
- Morton Grove Holidays
- Oakbrook Center Mall
- Palos Hills Holidays
- Rosemont Holidays
- Schaumburg Holidays
- Soldier Field
- Stone Park Holidays
- University of Illinois Chicago
- Walt Disney House
- West Chicago Holidays
- West Town Holidays
- Willis Tower
- Willowbrook Community Park
- Woodfield Mall
- Xtreme Trampolines
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
