Northwest Side Vacation Packages
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Top Northwest Side Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Omni Chicago Hotel
Downtown Chicago
Price was CA $1,561, price is now CA $1,139 per person
CA $1,139
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
This was a very clean and nice hotel. I enjoyed the room.
Reviewed on Jul 6, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,565, price is now CA $1,710 per person
CA $1,710
per person
Sep 16 - Sep 20
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We stayed in a Spacious one bedroom suite with full kitchen. Very clean and modern. The facilities are great but the steam room was out of order and the pool is not heated. I think you’d get more use if the pool if it was not so cold even in the end of June. The coffee/wine shop is really convenient. Will stay here again!
Reviewed on Jul 5, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,873, price is now CA $1,315 per person
CA $1,315
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back.
The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.
Reviewed on Jul 2, 2026
The Emily Hotel
Downtown Chicago
Price was CA $1,779, price is now CA $1,277 per person
CA $1,277
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)
Great boutique hotel in a great location! Definitely will stay here again when visiting Chicago.
Reviewed on Jul 5, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $1,760, price is now CA $1,278 per person
CA $1,278
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,013 reviews)
This location is ideal for families. The amenities provided are exceptional, scoring a perfect ten out of ten. It offers ample space for a family, including two bathrooms, which was greatly appreciated by my children. The property is well-equipped to ensure a comfortable stay. My only reservation pertains to its distance from Michigan Avenue and the Riverwalk, necessitating a vehicle to access these popular destinations. Otherwise, the experience was flawless.
Reviewed on Jul 2, 2026
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
3 out of top 10 points of interest in this area
Irving Park is well-liked for its restaurants and live music. If you're hoping to get in some sightseeing, Milwaukee Avenue and Irish American Heritage Center are top spots, and you can jump on the metro at Irving Park Station (Blue Line) or Addison Station (Blue Line) to get around.
Northwest Side Hotel Deals
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $247 per night from Jul 26 to Jul 27
CA $247
CA $294 total
Jul 26 - Jul 27
includes taxes & fees
8.2/10 Very good! (1,695 reviews)
"Tried to use the very small hair dryer only to find out it quite in a puff of black smoke and smelled up the whole room."
Reviewed on Jul 5, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from Jul 7 to Jul 8
CA $172
CA $205 total
Jul 7 - Jul 8
includes taxes & fees
8/10 Very good! (10,175 reviews)
"Good location, our shower didn't have much pressure but we managed, we will definitely be back. Bed was comfortable. Air was nice and ice cold lol"
Reviewed on Jul 6, 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from Jul 7 to Jul 8
CA $217
CA $305 total
Jul 7 - Jul 8
includes taxes & fees
9.2/10 Wonderful! (1,857 reviews)
"This was a very clean and nice hotel. I enjoyed the room."
Reviewed on Jul 6, 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 Side attractions
What to do in Northwest Side
Chicago: Navy Pier Centennial Wheel Ticket
CA $35
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $58
per adult
94% of travellers recommend
Frequently asked questions
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- Chicago Theatre
- Grant Park
- Visit Chicago
- Montrose Beach
- Northwestern University
- Water Tower Place
- Garfield Park Conservatory
- Lincoln Park Zoo
- Lakeview Vacations
- Chicago Riverwalk
- Buckingham Fountain
- Downtown Chicago Vacations
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- Unity Temple
- Ernest Hemingway Museum and House
- Frank Lloyd Wright Historic District
- United Center
- Golf Vacations
- Willis Tower
- Legoland® Discovery Center
- Wrigley Field
- 875 North Michigan Avenue
- Art Institute of Chicago
- Ann and Robert H. Lurie Children's Hospital
- Visit Downtown Chicago
- Rosemont Vacations
- Navy Pier
- Marina City
- Visit The Loop
- International Museum of Surgical Science
- The Loop Vacations
- Millennium Park
- Robie House
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
