Mayfair Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥109,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • Executive lounge
    Jul 11 - Jul 13

    Fairmont Chicago at Millennium Park + Flight

    Downtown Chicago
    2 nights
    4.5 star property
    8.8/10 - Excellent (2,187 reviews)
    "Clean room, overall nice hotel, restaurant was nice for happy hour. Lobby smelled like an old lady and peltons in gym were broken. Overall lovely stay."
    Reviewed June 9, 2026
    Roundtrip • Toronto (YYZ) - Chicago (ORD)
    YYZ - ORD • Nonstop ORD - YYZ • Nonstop
    ￥132,393
    ￥109,317
    per traveler
    found 1 day ago
    Fairmont Chicago at Millennium Park
  • Smart TV
    Aug 12 - Aug 18

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    6 nights
    4.0 star property
    9.2/10 - Wonderful (493 reviews)
    "Fully equipmet"
    Reviewed June 2, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥508,927
    ￥399,982
    per traveler
    found 14 hours ago
    Level Chicago Fulton Market
  • Front of property
    Jul 16 - Jul 20

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (4,401 reviews)
    "Very nice property in the middle of everything."
    Reviewed June 9, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥456,973
    ￥372,300
    per traveler
    found 1 day ago
    Hotel Riu Plaza Chicago
  • Breakfast and dinner served
    Jul 16 - Jul 20

    Omni Chicago Hotel + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.2/10 - Wonderful (1,799 reviews)
    "Best hotel in Chicago for the price. Perfect location. The staff was very friendly. The rooms are stylish and spacious. One minor inconvenience is that they do not offer room service but I was able to put an order in at the restaurant and pick up was fast and easy."
    Reviewed June 9, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥403,598
    ￥347,228
    per traveler
    found 1 day ago
    Omni Chicago Hotel
  • Terrace/patio
    Jul 16 - Jul 20

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (2,535 reviews)
    "This is an amazing place. Everything you can think of all under 1 roof. My hotel view was amazing. I am looking forward to coming annually."
    Reviewed June 8, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥427,032
    ￥370,394
    per traveler
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton

Where to stay in Mayfair

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

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 ￥21,776 per night from Jun 29 to Jun 30
￥21,776
￥25,890 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,232 reviews)
"The rooms were spacious and clean. Our room was not difficult to find. The building is old but historic. The place was well maintained and the staff were very helpful. Housekeeping only comes every other day unless requested. It worked for us. I would stay here again."

Reviewed on Jun 9, 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The price is ￥25,568 per night from Jul 1 to Jul 2
￥25,568
￥30,396 total
Jul 1 - Jul 2
includes taxes & fees
7.8/10 Good! (1,549 reviews)
"The hotel was amazing, the room was clean and big, the only bad thing was the check in… your employees are rude and disgusting… The girl from the breakfast and the guy from the rooftop were nice and respectful, we really like them"

Reviewed on Jun 9, 2026

The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is ￥25,505 per night from Jun 28 to Jun 29
￥25,505
￥29,070 total
Jun 28 - Jun 29
includes taxes & fees
8.8/10 Excellent! (2,640 reviews)
"Hotel was clean, very friendly staff and conveniently located from the airport"

Reviewed on Jun 9, 2026

Hyatt Regency O'Hare Chicago
See all 4,779 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 , 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

Wrigley Field

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

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.

Naval Base Great Lakes
Navy Pier

Navy Pier

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

Navy Pier

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥4,236
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

￥6,276
per adult
92% of travellers recommend
Art Institute of Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥6,354
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.