Mayfair Vacation Packages

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Top Holiday Package Deals in Mayfair

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was CA $1,018, price is now CA $551 per person
CA $551
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
Everything was very good; however, the soundproofing could be improved as we could clearly hear what was happening in the neighboring rooms

Reviewed on Sep 9, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,194, price is now CA $1,304 per person
CA $1,304
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
We picked the Trump Hotel-Chicago to celebrate our 35th Wedding Anniversary mainly for the location and the amenities. The hotel EXCEEDED our expectations in every way. (1) The staff is so warm, kind, compassionate and extremely professional in such a friendly down-to-earth way. (2) The property itself is immaculate. (3) The amenities: Terrace 16- the view will take your breath away! The food/cocktails were fabulous as was the service. (3) Pablo - Director of Rooms, Curtis -Concierge were off the charts fabulous. I wish I could remember all the staff names that went out of their way to make our weekend so special. I cannot wait to stay here again. As another reviewer said: put any political opinions aside and treat yourself to a stay here. YOU WILL LOVE IT. (There is no political aura here...only a fantastic team that wants you to enjoy your stay and they go out of their way to make sure you do).

Reviewed on Sep 8, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,137, price is now CA $699 per person
CA $699
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (347 reviews)
Pool area was great

Reviewed on Sep 4, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,124, price is now CA $694 per person
CA $694
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,014 reviews)
First time but won’t be the last. Very nice place with lots to do right around there.

Reviewed on Sep 9, 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was CA $955, price is now CA $609 per person
CA $609
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (2,078 reviews)
TV didn’t work correctly(Guide kept sticking). Need microwaves and better iron in rooms.

Reviewed on Sep 8, 2025

Where to stay in Mayfair

Find the best Mayfair areas and neighborhoods for the activities you enjoy most. Learn more about Mayfair
Downtown Chicago showing a city

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.

Find hotels in Downtown Chicago

Mayfair Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $204 per night from Sep 22 to Sep 23
CA $204
CA $239 total
Sep 22 - Sep 23
includes taxes & fees
Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $254 per night from Sep 22 to Sep 23
CA $254
CA $298 total
Sep 22 - Sep 23
includes taxes & fees
Embassy Suites by Hilton Chicago Downtown River North
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from Sep 23 to Sep 24
CA $168
CA $221 total
Sep 23 - Sep 24
includes taxes & fees
Freehand Chicago
See all 4,662 properties in Mayfair
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Mayfair vacation package cost?
Maybe less than you imagined — from only CA $551, as a matter of fact! By combining hotels, flights and car rentals into a tailor-made travel package, your trip to Mayfair is just a few clicks away.
How do I get a cheap travel package to Mayfair?
Bundle, bundle, bundle. Hotels, rental cars and flights — combine whatever you need into a Mayfair vacation package to save loads of cash. Score even bigger bargains when you add extras such as tours or experiences to your booking. But that's not the only good part. You have the flexibility to put together your vacation your way. We offer more than 550 partner airlines and 1,000,000 properties throughout the world, so that everyone has a chance to travel and fulfill those vacation dreams.
Where should I stay in Mayfair?
With fascinating attractions like Portage Park and Six Corners in this area, look for a hotel situated near them. Walt Disney House is another sight in Mayfair that people flock to.
How far in advance should I book my Mayfair vacation?
While not all airlines release tickets early, it's usually possible to look up international airfares on Expedia up to 12 months in advance. This is the time you'll nab some incredible deals. If you've left everything to the last minute, you may still be in luck. Sometimes the lowest prices appear only weeks prior to departure.
What should I know before booking a Mayfair travel package?
You'll score impressive savings when you bundle your flights, hotels and rental cars into a package. Not just that, booking everything together simply makes planning easier. So why waste your money or time? Whether you're organizing a ritzy city getaway or a low-cost family road trip, browse our vacation packages today.
Can I choose my airline with a Mayfair Expedia vacation package?
You can, and with over 550 airlines to choose from around the world, you've got lots of choice. Scroll through the available options and find out which airline suits your budget and needs.
If I'm not able to travel, can I cancel my Mayfair vacation package?
It's impossible to predict what tomorrow might bring, so it's good to know that you can cancel or change your Mayfair vacation package. If you made your booking in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to learn more.

Discover the most popular places to visit in Mayfair

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

4.5/5(19 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier

Navy Pier

4.5/5(459 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

CA $67
per adult
96% of travellers recommend
Architecture River Tour
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $47
per adult
94% of travellers recommend
Color Factory Chicago Ticket
Relax and enjoy the view

Chicago Architecture Center River Cruise aboard First Lady

CA $77
per adult
96% of travellers recommend
Chicago Architecture Center River Cruise aboard First Lady
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.