Des Plaines Holidays
Photo by W. Ross Wells
- Plan, book, travel with confidence
Better together
Save up to €185 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Des Plaines
Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was €1,041, price is now €730 per person
€730
per person
17 Nov - 24 Nov
found 7 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (291 reviews)
Had a great uneventful stay
Reviewed on 22 Sept 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €2,036, price is now €1,291 per person
€1,291
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Perfect location, beautiful view, nice staffs, excellently maintained room and facility!
Reviewed on 28 Sept 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was €1,484, price is now €962 per person
€962
per person
17 Nov - 24 Nov
found 7 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
Good location not far from all the big attractions. But it was noisy in the evening.
Reviewed on 29 Sept 2025
The Emily Hotel
Downtown Chicago
Price was €1,545, price is now €1,032 per person
€1,032
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
Beautiful hotel in great walkable area. There were major renovations going on while we were there so our actual floor was a bit messy/busy, although the common areas remained lovely. Would stay again for the good location. All staff very nice.
Reviewed on 29 Sept 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was €1,269, price is now €859 per person
€859
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The WIt was everything. The Roof at the Wit, was amazing, be sure to make reservations. I love this hotel and Chicago it was safe and close to everything!!
Reviewed on 26 Sept 2025
Top hotels in Des Plaines
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
7.8/10 Good! (9,338 reviews)
"This was our second stay at this hotel and we will probably stay here for all our future trips to Chicago. It's very conveniently located, making it very easy to get to and from Midway Airport and all the things we want to see and do in town. There are tons of great restaurants within walking distance ..."
Reviewed on 28 Sept 2025
Freehand Chicago
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €139 per night from 27 Oct to 28 Oct
€139
27 Oct - 28 Oct
includes taxes & fees
7.8/10 Good! (2,388 reviews)
"It felt cozy and comfortable. The room was a little bit dusty and the night light was not working."
Reviewed on 24 Sept 2025
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is €195 per night from 19 Oct to 20 Oct
€195
19 Oct - 20 Oct
includes taxes & fees
8.4/10 Very Good! (4,985 reviews)
"Clean room, staff was friendly & helpful. Location was perfect for us"
Reviewed on 25 Sept 2025
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 Des Plaines
Chicago By Night River & Lake Cruise
€38
per adult
96% of travellers recommend
Chicago Sightseeing River and Lake Cruise
€38
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
