Northwest Chicago Vacation Packages
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Top Northwest Chicago Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,121, price is now CA $782 per person
CA $782
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Staff was very friendly and helpful. Room was clean. Free coffee and fruit in the AM.
Reviewed on Jul 9, 2026
Omni Chicago Hotel
Downtown Chicago
Price was CA $1,834, price is now CA $1,264 per person
CA $1,264
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
Room was clean and large, staff were helpful and polite. Would definitely stay again!
Reviewed on Jul 10, 2026
JW Marriott Chicago
Downtown Chicago
Price was CA $1,768, price is now CA $1,221 per person
CA $1,221
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
What a great excellent and friendly welcome front desk personnel. The lady on who worked on Saturday afternoon was amazing. Didn’t catch her name but she was very nice and welcoming
Reviewed on Jul 5, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,287, price is now CA $1,612 per person
CA $1,612
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.
Reviewed on Jul 9, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $1,693, price is now CA $1,216 per person
CA $1,216
per person
Sep 12 - Sep 15
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Amazing and beautiful hotel with caring and helpful staff!
Reviewed on Jul 8, 2026
Northwest Chicago Hotel Deals
The Westin Chicago Northwest
400 Park Blvd Itasca IL
Fully refundableReserve now, pay when you stay
The price is CA $216 per night from Aug 9 to Aug 10
CA $216
CA $241 total
Aug 9 - Aug 10
includes taxes & fees
8.8/10 Excellent! (1,016 reviews)
"Clean and big rooms very friendly staff"
Reviewed on Jul 8, 2026
Eaglewood Resort and Spa
1401 Nordic Rd Itasca IL
The price is CA $156 per night from Aug 9 to Aug 10
CA $156
CA $204 total
Aug 9 - Aug 10
includes taxes & fees
8.8/10 Excellent! (1,207 reviews)
"95 decrease and we had a room with no air. The front desk manager was very rude. Not interested at all in transferring us to another room. We were told to be patient or check out. We arrived at 1:30 and it wasn’t until 7:00 we were finally transferred to another room."
Reviewed on Jul 10, 2026
Hyatt Place Itasca
1150 North Arlington Heights Road Itasca IL
Fully refundableReserve now, pay when you stay
The price is CA $180 per night from Aug 9 to Aug 10
CA $180
CA $200 total
Aug 9 - Aug 10
includes taxes & fees
8.8/10 Excellent! (1,184 reviews)
"Muy bien todo deben varias un poco el desayno ya que nos quedamos una semana y era lo mismo. Lo demas muy bueno tido y limpio y el aerea super accesible."
Reviewed on Jul 9, 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.
Stay near popular Northwest Chicago attractions
What to do in Northwest Chicago
Chicago: Navy Pier Centennial Wheel Ticket
CA $35
per adult
88% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $64
per adult
94% of travellers recommend
Frequently asked questions
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- Ernest Hemingway Museum and House
- Golf Vacations
- Morton Arboretum
- Northwestern University
- Woodfield Mall
- Algonquin Vacations
- Chicago Theatre
- Unity Temple
- Visit The Loop
- United Center
- Willis Tower
- Lakeview Vacations
- Visit Hoffman Estates
- Visit Elk Grove Village
- Art Institute of Chicago
- Buckingham Fountain
- Grant Park
- Chicago Riverwalk
- Chicago Vacations
- Rosemont Vacations
- Garfield Park Conservatory
- Santa's Village
- Downtown Chicago Vacations
- Frank Lloyd Wright Historic District
- Visit Schaumburg
- Water Tower Place
- Millennium Park
- Legoland® Discovery Center
- Lincoln Park Zoo
- Six Flags Great America
- Wrigley Field
- Centennial Beach
- Navy Pier
- Visit Downtown Chicago
- Montrose Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
