Northwest Side Vacation Packages
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Top Northwest Side Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hilton Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,986 reviews)
For a four star hotel in chicago it is very pricy only good for location as the amenities and extras are what you gt in a 3 star hotel outside of the city. The carpet is dated and dusty, the bathroom was clean and more modern than expected, but it is not as expected.
Reviewed on Jul. 16, 2025
Virgin Hotels Chicago
Downtown Chicago
Save 100% on your flight
per person
Sep 4 - Sep 9
found 22 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I loved the location of the property, and the overall concept of something fun and funky, but I had a "higher end" room, and it was right near the elevator, so I got a lot of noise on that side, plus the El from the other side. The rug wasn't super clean (although the bedding and the rest of the room were a delight). The most annoying thing was the TV. Anything I turned it to, 10 minutes later to the minute, it went back to the Virgin channel #1, here are all our hotels in the world. I really hated having to stay on top of a show, when usually I want the tv on as background while I'm getting ready, etc. Also, this hotel's amenities were oversold, i.e., good luck getting on the rooftop, especially if you just wanted a quiet sip of a drink. I loved the cafe and the staff, though, everyone was very pleasant.
Reviewed on Jul. 15, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
Sep 4 - Sep 9
found 22 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Excellent stay - outstanding Director of Rooms and valet staff made my daughters wedding an amazing experience - just outstanding !!
Reviewed on Jul. 16, 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.
Northwest Side Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $202 per night from Aug 5 to Aug 6
CA $202
CA $238 total
Aug 5 - Aug 6
includes taxes & fees
7.8/10 Good! (8,979 reviews)
"The hotel is an old property, but the bedrooms were nicely renovated. The location is the highlight... nice views, close to everything, walkable distance to downtown and the lake."
Reviewed on Jul. 15, 2025
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is CA $289 per night from Aug 10 to Aug 11
CA $289
CA $383 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (2,045 reviews)
"Very close to popular places."
Reviewed on Jul. 16, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $199 per night from Aug 10 to Aug 11
CA $199
CA $234 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (2,444 reviews)
"clean...close to attractions.."
Reviewed on Jul. 14, 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.
Discover the most popular places to visit in Northwest Side
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
What to do in Northwest Side
Wendella's 90-min Chicago River Architecture Tour
CA $62
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
CA $62
per adult
94% of travellers recommend
Frequently asked questions
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Flights
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.