Mayfair Vacation Packages
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Top Holiday Package Deals in Mayfair
Price found within the past 48 hours. Click for updated prices.
Chicago Marriott Downtown Magnificent Mile
Downtown Chicago
Price was CA $869, price is now CA $607 per person
CA $607
per person
May 22 - May 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,001 reviews)
Staff, location, food very good but the rooms were meh… fine but was expecting more
Reviewed on Apr 10, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,834, price is now CA $1,197 per person
CA $1,197
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
We love staying at the Sable. Easy in and out parking. The Valet staff is wonderful. We enjoyed our breakfast. The room and view is always amazing.
Reviewed on Apr 11, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,376, price is now CA $968 per person
CA $968
per person
May 26 - May 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,123 reviews)
The staff at the Pendry are top notch. We arrived early and just wanted to drop our bags off, but the staff was able to check us in several hours early. Upon learning it was my birthday, the bell hop brought me a glass of wine from the bar and later, the staff sent up a bottle of prosecco and birthday cupcakes. Our room
Reviewed on Apr 7, 2026
Le Méridien Essex Chicago
Downtown Chicago
Price was CA $2,134, price is now CA $1,509 per person
CA $1,509
per person
Jun 19 - Jun 23
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.8/10 Excellent! (1,013 reviews)
Le Meridien Exxex Chicago is in the perfect location, steps from where I need to be when visiting Chicago. The staff are super helpful and friendly. The restaurant serves delicious food and the waitstaff is attentive. Keep up the good work!
Reviewed on Apr 3, 2026
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was CA $2,415, price is now CA $1,715 per person
CA $1,715
per person
May 20 - May 27
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.2/10 Wonderful! (371 reviews)
Breakfast was good. Room was clean with great air-conditioned. Staff very nice and happy. Customer service great. Had a great experience. Will be back and would recommend to everyone.
Reviewed on Apr 11, 2026
Where to stay in Mayfair
Find the best Mayfair areas and neighborhoods for the activities you enjoy most. Learn more about Mayfair
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.
Mayfair Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $171 per night from Apr 26 to Apr 27
CA $171
CA $200 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (10,096 reviews)
Storage luggage staff was great and helpful. Had to move rooms due to the shower being dirty and water was not draining. Second room had brown water coming out when you turned the shower on, after 5 minutes it would go away.
Reviewed on Apr 11, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from Apr 26 to Apr 27
CA $165
CA $194 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (4,107 reviews)
Don’t book through Expedia, I had to leave my vacation early because I had to rush my travel companion to the ER as they were struggling to breathe. Great hotel, just don’t book through Expedia. You will have problems.
Reviewed on Apr 11, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $215 per night from Apr 19 to Apr 20
CA $215
CA $253 total
Apr 19 - Apr 20
includes taxes & fees
8.6/10 Excellent! (5,844 reviews)
Ok
Reviewed on Apr 12, 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 Mayfair
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
98% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.