
Oak Brook Holidays
Photo by Judy Mahoney
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Top Flight + Hotel Deals in Oak Brook
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was €1,017, price is now €689 per person
€689
per person
2 Mar - 7 Mar
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
I wouldn’t say a 5 star hotel I would say 3.5 because their was no microwave access in room or no where on property no valet parking had to park across the street in self parking deck for $55 per night and it wasn’t throughly explained how parking went in parking deck so we end up paying extra for parking plus the $55 per night. They only give you 10/15 min to park in front of hotel to unload and load. There were no robes in room, tv was hard to work, covers on bed was paper thin. You cant bring breakfast upstairs you have to be seated.
Reviewed on 14 Jan 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was €1,702, price is now €1,115 per person
€1,115
per person
2 Mar - 7 Mar
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing
Reviewed on 13 Jan 2026


Level Chicago – Old Town
Downtown Chicago
Price was €1,099, price is now €785 per person
€785
per person
2 Mar - 7 Mar
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
I stayed 5 nights total, 4 nights in a two BR, 1 bath with a balcony and the last night in a one BR. The 2BR was great. It faced East, received a lot of sunlight, was clean, modern and the bed was very comfortable. The gym had what I needed too. actually liked sleeping with the sound of the el nearby because I used to live in the area. I did not give it 5 stars because the walls are super thin. Someone had a party next to me and it was impossible to sleep hearing voices straight through the walls. Being a newer building, I don’t think the best quality appliances or fixtures were chosen. My ice machine wasn’t working and the heat/fan only worked in certain areas in the 2BR. Additional lighting should be added. The 1BR shower fixtures and drain needed some attention. That said, Mihajlo and the front desk staff were very helpful and attentive and helped me with whatever I needed. The 1BR seemed more like a studio to m. I’d prefer to book directly through Level, but it was a better price with Expedia. I still thought it was pricey but I was overall happy with my stay.
Reviewed on 12 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 €157 per night from 1 Feb to 2 Feb
€157
1 Feb - 2 Feb
includes taxes & fees
8.4/10 Very Good! (2,523 reviews)
Yes great Hotel everything was perfect
Reviewed on 12 Jan 2026

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is €90 per night from 1 Feb to 2 Feb
€90
1 Feb - 2 Feb
includes taxes & fees
8.8/10 Excellent! (3,706 reviews)
10/10
Reviewed on 14 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 €82 per night from 27 Jan to 28 Jan
€82
27 Jan - 28 Jan
includes taxes & fees
8.6/10 Excellent! (2,059 reviews)
Good.
Reviewed on 13 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
4.5/5(40 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Michigan Avenue
4.5/5(14 reviews)
You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Navy Pier
4/5(125 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Oak Brook

Skydeck - Willis Tower Admission
€38
per adult
98% of travellers recommend

Chicago: Navy Pier Centennial Wheel Ticket
€21
per adult
88% of travellers recommend
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