Palmer Square Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in Palmer Square
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,003, price is now CA $755 per person
CA $755
per person
Jun 22 - Jun 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,144 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!
Reviewed on May 5, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,968, price is now CA $1,453 per person
CA $1,453
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,122 reviews)
Great staff and perfect place to be in the middle of everything!
Reviewed on Apr 27, 2026
Hilton Chicago O'Hare Airport
O'Hare
Price was CA $1,123, price is now CA $834 per person
CA $834
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (2,281 reviews)
Wonderful location, staff were very helpful and room was clean. Older hotel but well maintained. Pricey but worthwhile for convenience sake.
Reviewed on May 5, 2026
Where to stay in Palmer Square
Find the best Palmer Square areas and neighborhoods for the activities you enjoy most. Learn more about Palmer Square
Downtown Chicago
4 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.
Palmer Square Hotel Deals
Hotel Felix River North/Magnificent Mile
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $429 per night from Jun 7 to Jun 8
CA $429
CA $552 total
Jun 7 - Jun 8
includes taxes & fees
8.2/10 Very Good! (2,697 reviews)
great location
Reviewed on May 9, 2026
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 11 to May 12
CA $183
CA $217 total
May 11 - May 12
includes taxes & fees
8/10 Very Good! (10,189 reviews)
Room was clean, coffee maker didn’t work but was replaced quickly. Staff all very helpful, especially Steve the doorman/security. Very helpful getting us a cab!
Reviewed on May 8, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $423 per night from May 19 to May 20
CA $423
CA $502 total
May 19 - May 20
includes taxes & fees
8.8/10 Excellent! (5,187 reviews)
As soon as we arrived Hotel Staff was very friendly and helpful. Valet parking was very convenient.
Reviewed on May 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.
Frequently asked questions
Discover the most popular places to visit in Palmer Square
Wrigley Field
4.5/5(159 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
4.5/5(3 reviews)
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
4.5/5(460 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Skydeck - Willis Tower Admission
CA $61
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.