West Pullman Vacation Packages
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- Fairmont Chicago at Millennium Park
Jul 28 - Aug 2Fairmont Chicago at Millennium Park + Flight
Downtown Chicago5 nights8.8/10 - Excellent (2,163 reviews)"Lovely stay and we are at Toro right in the hotel. Fabulous dinner"Reviewed May 18, 2026Roundtrip • Toronto (YYZ) - Chicago (ORD)YYZ - ORD • Nonstop ORD - YYZ • NonstopCA $2,195CA $1,510found 18 hours agoper traveller - Swissotel - Chicago
Jul 28 - Aug 2Swissotel - Chicago + Flight
Downtown Chicago5 nights9.0/10 - Wonderful (3,332 reviews)"Very good Outstanding service "Reviewed May 19, 2026Roundtrip • Toronto (YYZ) - Chicago (ORD)YYZ - ORD • Nonstop ORD - YYZ • NonstopCA $3,626CA $1,987found 18 hours agoper traveller - Sable at Navy Pier Chicago, Curio Collection by Hilton
Jul 28 - Aug 2Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight
Downtown Chicago5 nights9.4/10 - Exceptional (2,506 reviews)"I loved it here and will definitely stay again."Reviewed May 18, 2026Roundtrip • Toronto (YYZ) - Chicago (ORD)YYZ - ORD • Nonstop ORD - YYZ • NonstopCA $2,965CA $1,891found 18 hours agoper traveller - LondonHouse Chicago, Curio Collection by Hilton
Jul 28 - Aug 2LondonHouse Chicago, Curio Collection by Hilton + Flight
Downtown Chicago5 nights9.4/10 - Exceptional (3,728 reviews)"Great location with a great view. Walking distance to all attractions and restaurants. The room was spacious and comfy beds"Reviewed May 18, 2026Roundtrip • Toronto (YYZ) - Chicago (ORD)YYZ - ORD • Nonstop ORD - YYZ • NonstopCA $3,410CA $2,288found 18 hours agoper traveller - Hotel Felix River North/Magnificent Mile
Jul 28 - Aug 2Hotel Felix River North/Magnificent Mile + Flight
Downtown Chicago5 nights8.2/10 - Very good (2,711 reviews)"Staff is excellent. Breakfast was below standards - muffins, fruit, juice, and a couple breakfast sandwiches the staff put in the microwave. I’d pass on the breakfast. Nice location. Rooms were okay - the bed in our room was full of cat scratches."Reviewed May 18, 2026Roundtrip • Toronto (YYZ) - Chicago (ORD)YYZ - ORD • Nonstop ORD - YYZ • NonstopCA $2,379CA $1,605found 18 hours agoper traveller
Where to stay in West Pullman
Find the best West Pullman areas and neighborhoods for the activities you enjoy most. Learn more about West Pullman
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
West Pullman Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $183 per night from May 26 to May 27
CA $183
CA $218 total
May 26 - May 27
includes taxes & fees
8/10 Very Good! (10,164 reviews)
"The cool thing about the location is that it's close to a park for scenery, the museum, the art institute and baseball field. The older side of the hotel needs updating in their rooms, and needs a bigger or faster elevator. A.C/heater panel was stuck, so needed someone to get it opened. The floor ..."
Reviewed on May 19, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $205 per night from May 25 to May 26
CA $205
CA $283 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (4,187 reviews)
"My husband and I really enjoyed staying at Hotel Riu Plaza Chicago. Staff was friendly and helpful. Hotel is very clean. Breakfast & bar is so delicious we definitely will come back. Chi Love you! Thank you so much."
Reviewed on May 19, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from May 25 to May 26
CA $167
CA $198 total
May 25 - May 26
includes taxes & fees
7.8/10 Good! (1,433 reviews)
"BEWARE: I booked and paid for this hotel a month in advance. My train was delayed a few hours, so I arrived at the hotel about 7pm. However, I completed an echeck-in at the hotels request at 1pm. Upon arriving, there was a short line of people waiting to check-in and they were upset and asking to ..."
Reviewed on May 19, 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.
Frequently asked questions
Discover the most popular places to visit in West Pullman
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Skydeck - Willis Tower Admission
CA $60
per adult
96% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.