Northwest Side Holidays
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Top Flight + Hotel Deals in Northwest Side
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was €921, price is now €686 per person
€686
per person
31 Oct - 4 Nov
found 20 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
Nice hotel but room was extremely small.
Reviewed on 11 Sept 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was €1,831, price is now €1,190 per person
€1,190
per person
31 Oct - 4 Nov
found 20 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Great bar on the 16th floor. Staff was great
Reviewed on 10 Sept 2025
Pendry Chicago
Downtown Chicago
Price was €1,257, price is now €924 per person
€924
per person
31 Oct - 4 Nov
found 20 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,070 reviews)
The property is gorgeous! Lovely rooms and the staff were fantastic, could not fault them at all! My only issue would be the roads outside are very noisy, we needed ear plugs to sleep. Other than that, absolutely fantastic stay! Would return and would highly recommend
Reviewed on 8 Sept 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was €1,138, price is now €853 per person
€853
per person
31 Oct - 4 Nov
found 20 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,363 reviews)
Hotel was wonderful. Staff was excellent. Great location with lots of walkable activities.
Reviewed on 11 Sept 2025
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was €919, price is now €695 per person
€695
per person
31 Oct - 4 Nov
found 20 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,115 reviews)
Property was in a very convenient and walkable location. Staff was very friendly and attentive.
Reviewed on 11 Sept 2025
Where to stay in Northwest Side
Find the best Northwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Northwest Side
Irving Park
2 out of top 10 points of interest in this area
Appreciated for its restaurants and live music, you might consider exploring Irving Park. Check out the variety of things to see and do like Milwaukee Avenue, and jump on the metro at Irving Park Station (Blue Line) or Montrose Station (Blue Line) to get around the city.
Top hotels in Northwest Side
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €198 per night from 4 Oct to 5 Oct
€198
4 Oct - 5 Oct
includes taxes & fees
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is €176 per night from 22 Sept to 23 Sept
€176
22 Sept - 23 Sept
includes taxes & fees
Freehand Chicago
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €137 per night from 22 Sept to 23 Sept
€137
22 Sept - 23 Sept
includes taxes & fees
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 Northwest Side
Wendella's 90-min Chicago River Architecture Tour
€35
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
€39
per adult
96% of travellers recommend
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Flights
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
