Mayfair Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Top Holiday Package Deals in Mayfair

Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile

Downtown Chicago

CA $935

per person

Nov 27 - Dec 2

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.2/10 Very good! (3,105 reviews)

Great place to stay! The location is excellent, close to plenty of restaurants and just one mile from Millennium Park. Subway and bus stations are also nearby, making it easy to get around the city. The staff is very friendly and welcoming. I would definitely recommend this place!

Reviewed on Oct 20, 2026

The Talbott, Autograph Collection

Downtown Chicago

Save 100% on your flight

CA $1,159

per person

Nov 27 - Dec 2

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (179 reviews)

Nice property overall Room was very nice Location excellent

Reviewed on Oct 19, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

CA $1,336

per person

Nov 27 - Dec 2

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (576 reviews)

Hotel Saint Clair- Magnificent Mile

Downtown Chicago

CA $1,151

per person

Nov 27 - Dec 2

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.6/10 Excellent! (2,274 reviews)

Good location, small rooms,

Reviewed on Oct 20, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

CA $1,754

per person

Dec 5 - Dec 8

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (2,035 reviews)

Where to stay in Mayfair

Find the best Mayfair areas and neighborhoods for the activities you enjoy most. Learn more about Mayfair

A busy city street with tall buildings, a bus, and cars.

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.

A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

A wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

Mayfair Hotel Deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

CA $147

CA $175 total

Nov 10 - Nov 11

includes taxes & fees

8/10 Very good! (10,170 reviews)

"Room was great. They are doing some remodeling. Could not find a thermostat in my room."

Reviewed on Oct 20, 2026

River Hotel

75 East Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

CA $215

CA $255 total

Nov 1 - Nov 2

includes taxes & fees

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

CA $170

CA $202 total

Nov 11 - Nov 12

includes taxes & fees

8/10 Very good! (2,544 reviews)

"Basically no amenities"

Reviewed on Oct 20, 2026

See all 4,859 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.

Frequently asked questions

How much does a Mayfair vacation package cost?

Maybe less than you imagined — from only CA $935, 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.