Mayfair Holidays

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    Better together

    Save up to €185 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was €1,041, price is now €730 per person
€730
per person
17 Nov - 24 Nov
found 10 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (291 reviews)
Had a great uneventful stay

Reviewed on 22 Sept 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €2,036, price is now €1,291 per person
€1,291
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Perfect location, beautiful view, nice staffs, excellently maintained room and facility!

Reviewed on 28 Sept 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,484, price is now €962 per person
€962
per person
17 Nov - 24 Nov
found 10 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
Good location not far from all the big attractions. But it was noisy in the evening.

Reviewed on 29 Sept 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was €1,545, price is now €1,032 per person
€1,032
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
Beautiful hotel in great walkable area. There were major renovations going on while we were there so our actual floor was a bit messy/busy, although the common areas remained lovely. Would stay again for the good location. All staff very nice.

Reviewed on 29 Sept 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was €1,269, price is now €859 per person
€859
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The WIt was everything. The Roof at the Wit, was amazing, be sure to make reservations. I love this hotel and Chicago it was safe and close to everything!!

Reviewed on 26 Sept 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 which includes 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

Top hotels in Mayfair

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
7.8/10 Good! (9,338 reviews)
"This was our second stay at this hotel and we will probably stay here for all our future trips to Chicago. It's very conveniently located, making it very easy to get to and from Midway Airport and all the things we want to see and do in town. There are tons of great restaurants within walking distance ..."

Reviewed on 28 Sept 2025

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Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €139 per night from 27 Oct to 28 Oct
€139
27 Oct - 28 Oct
includes taxes & fees
7.8/10 Good! (2,388 reviews)
"It felt cozy and comfortable. The room was a little bit dusty and the night light was not working."

Reviewed on 24 Sept 2025

Freehand Chicago
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
The price is €195 per night from 19 Oct to 20 Oct
€195
19 Oct - 20 Oct
includes taxes & fees
8.4/10 Very Good! (4,985 reviews)
"Clean room, staff was friendly & helpful. Location was perfect for us"

Reviewed on 25 Sept 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,709 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 holiday package cost?
Maybe less than you imagined — from only €730, 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 holiday 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 holiday 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 fulfil those holiday 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 holiday?
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 organising a ritzy city getaway or a low-cost family road trip, browse our holiday packages today.
Can I choose my airline with a Mayfair Expedia holiday 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 holiday package?
It's impossible to predict what tomorrow might bring, so it's good to know that you can cancel or change your Mayfair holiday 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.

Popular places to visit

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

Wrigley Field

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

Wrigley Field
Magnificent Mile - River North showing street scenes, signage and night scenes

Michigan Avenue

You can find the perfect gifts to bring home 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

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

Navy Pier

Things to do

See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

€38
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

€38
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
River tour boat in Chicago

Architecture River Tour

€42
per adult
96% of travellers recommend
Architecture River 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.