Mayfair Vacations from ￥295,940

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  • Better together

    Save up to ￥85,000 when you book a flight and hotel together*

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

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The Latest Mayfair Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥379,770, price is now ￥295,940 per person
￥295,940
per person
Jul 9 - Jul 13
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,914 reviews)
Great staff, very attentive to needs, very helpful

Reviewed on Apr 24, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥480,293, price is now ￥375,986 per person
￥375,986
per person
Jul 9 - Jul 13
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Great staff, facilities, esp the fitness & spa

Reviewed on Apr 23, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was ￥503,980, price is now ￥400,476 per person
￥400,476
per person
Jul 9 - Jul 13
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
Beautiful hotel, I will be returning

Reviewed on Apr 21, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was ￥405,438, price is now ￥330,630 per person
￥330,630
per person
Jul 9 - Jul 13
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,137 reviews)
Great hotel! Very central location, helpful staff. The speak easy was a great surprise

Reviewed on Apr 20, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was ￥394,981, price is now ￥332,408 per person
￥332,408
per person
Jun 11 - Jun 15
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great staff, full kitchen and living room, good location, friendly people, safe. I would stay here again.

Reviewed on Apr 23, 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

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 ￥19,915 per night from Apr 26 to Apr 27
￥19,915
￥23,380 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (10,133 reviews)
wifi wouldn’t connect, when we called the front desk to ask (I had work I needed to do, and specifically checked before booking that the room included wifi) was met with attitude to “just connect” even though the wifi network wasn’t visible or available. also, you have no control over the temperature ...

Reviewed on Apr 24, 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is ￥18,831 per night from May 26 to May 27
￥18,831
￥22,390 total
May 26 - May 27
includes taxes & fees
8.8/10 Excellent! (5,125 reviews)
Wonderful and helpful sstaff. Excellent location

Reviewed on Apr 24, 2026

River Hotel
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥13,834 per night from Apr 26 to Apr 27
￥13,834
￥21,102 total
Apr 26 - Apr 27
includes taxes & fees
8.2/10 Very Good! (2,636 reviews)
The staff were extremely impressed and helpful. Help me with restaurant choices, where to go for tours. Only thing I regretted was not packing the proper clothes for the chance of weather. It was my personal birthday present to me and I did enjoyed myself.

Reviewed on Apr 24, 2026

Hotel Felix River North/Magnificent Mile
See all 4,917 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 ￥295,940, 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

￥4,289
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

￥7,012
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

￥6,375
per adult
92% of travellers recommend
Art Institute of Chicago
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.