Oak Park Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €185 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
Top Flight + Hotel Deals in Oak Park
Price found within the past 48 hours. Click for updated prices.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was €834, price is now €694 per person
€694
per person
19 Feb - 23 Feb
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
I thoroughly enjoyed this hotel. Many stylish and thoughtful touches. The housekeeping staff did a great job. I stayed 7 nights and could’ve easily stayed 7 more.
Reviewed on 13 Jan 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was €1,103, price is now €744 per person
€744
per person
19 Feb - 23 Feb
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Cleanliness, exceptional customer service, and a complimentary upgrade made our stay outstanding! The way the buffet staff efficiently managed the line, guided guests to tables, and consistently kept the food fresh—all while wearing genuine smiles—was truly impressive. Our room was spotless, modern, and well-stocked, exceeding our expectations. We will definitely be back!
Reviewed on 11 Jan 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was €872, price is now €736 per person
€736
per person
19 Feb - 23 Feb
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
Clean room, amazinggggg views, everyone was so nice. Must go downstairs to Toro and get a martini from John!!
Reviewed on 10 Jan 2026
Top hotels in Oak Park
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is €165 per night from 20 Jan to 21 Jan
€165
20 Jan - 21 Jan
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 25 Jan to 26 Jan
€90
25 Jan - 26 Jan
includes taxes & fees
8.8/10 Excellent! (3,672 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 €84 per night from 14 Jan to 15 Jan
€84
14 Jan - 15 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
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
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
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Oak Park
Skydeck - Willis Tower Admission
€38
per adult
98% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
€21
per adult
88% of travellers recommend
Explore a world of travel with Expedia
- 4 Star Hotels in Northwest Side
- 5 Star Hotels in Belmont Cragin
- 5 Star Hotels in Northwest Side
- 5 Star Hotels in River Forest
- Albany Park Hotels
- Hotels near Anna and Frederick Douglass Park
- Austin Hotels
- Avondale Hotels
- Belmont Cragin Hotels
- Berwyn Hotels
- Chicago Hotels
- Beach Hotels in Cicero
- Cicero Hotels
- East Garfield Park Hotels
- East Village Hotels
- Lgbt-Friendly Hotels in Elmwood Park
- B&B in Forest Park
- The Peninsula Group Hotels in Forest Park
- Forest Park Hotels
- Hotels near Frank Lloyd Wright Historic District
- Humboldt Park Hotels
- Irving Park Hotels
- La Grange Park Hotels
- Logan Square Hotels
- Lyons Hotels
- Mayfair Hotels
- Maywood Hotels
- Melrose Park Hotels
- Montclare Hotels
- Near West Side Hotels
- North Lawndale Hotels
- Resorts in North Riverside
- Cheap Hotels in Oak Park
- Luxury Hotels in Oak Park
- Romantic Hotels in Oak Park
- Oak Park Hotels
- Holiday Homes in Oak Park Station
- Lgbt-Friendly Hotels in O'Hare
- O'hare Hotels
- Apartments in River Forest
- Red Roof Inn Hotels in River Forest
- Sage Hospitality Hotels in River Forest
- River Forest Hotels
- Cheap Hotels in Schiller Park
- Ukrainian Village Hotels
- United Center Hotels
- Aparthotels in West Side
- Hostels in West Side
- Advocate Illinois Masonic Medical Center
- Ann and Robert H. Lurie Children's Hospital
- Anshe Emet Synagogue
- Apollo Theater Chicago
- Athenaeum Theatre
- Berwyn Holidays
- Visit Broadview
- Canalport Riverwalk Park
- Visit Dunning
- Visit Jefferson Park
- Visit Noble Square
- Visit North Lawndale
- Chicago Place Mall
- Visit Ukrainian Village
- Visit United Center
- Chicago Holidays
- Cloud Gate
- Countryside Holidays
- Credit Union 1 Arena
- Edge Ice Arena
- Ernest Hemingway Museum and House
- Visit Forest Park
- Frank Lloyd Wright Historic District
- Garfield Park Conservatory
- Grant Park
- Visit Harwood Heights
- Visit Hillside
- Visit La Grange Park
- Lincoln Hall
- Michigan Avenue
- Norridge Holidays
- Visit Oak Park
- Prentice Women's Hospital
- River Forest Holidays
- Sunset Bridge Meadow
- Unity Temple
- University of Illinois Chicago
- Water Tower Place
- Willis Tower
- Wrigley Building
- Wrigley Field
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
