Mayfair Holidays from £1,100

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Your Mayfair Holiday

Take the fuss out of planning your next getaway by booking a Mayfair holiday package. Soak in the sights and sounds of this unique neighbourhood and experience all it has to offer. Your trip to Mayfair wouldn't be complete without a stop at popular attractions nearby such as Portage Park, Milwaukee Avenue and Six Corners. Expedia is here to help put your plans into action. Book your dream Mayfair holiday today.

Price found within the past 48 hours. Click for updated prices.
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Price was £1,398, price is now £1,100 per person
£1,100
per person
19 Apr - 25 Apr
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,266 reviews)
Everything was great. Love the restaurant and bar, staff was friendly and helpful

Reviewed on 14 Jan 2026

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,155, price is now £1,445 per person
£1,445
per person
19 Apr - 25 Apr
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.

Reviewed on 26 Jan 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £1,950, price is now £1,424 per person
£1,424
per person
19 Apr - 25 Apr
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.

Reviewed on 3 Feb 2026

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was £1,569, price is now £1,242 per person
£1,242
per person
19 Apr - 25 Apr
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,129 reviews)
I’ve had the pleasure of a stay at this hotel more than a few times now and it’s right up there with the Four Seasons and Peninsula, which I adore, but the design is a step above. Friendly but demure staff and a fabulous location…steps away from a number of gorgeous restaurants and my go-to and frequented boutiques when I’m in town. ⭐️⭐️⭐️⭐️⭐️

Reviewed on 3 Feb 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £1,443, price is now £1,184 per person
£1,184
per person
27 Mar - 1 Apr
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.

Reviewed on 31 Jan 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 featuring 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
Fully refundableReserve now, pay when you stay
The price is £77 per night from 8 Feb to 9 Feb
£77
8 Feb - 9 Feb
includes taxes & fees
8/10 Very Good! (9,848 reviews)
Wonderful hotel

Reviewed on 4 Feb 2026

Congress Plaza Hotel
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
300 E Ohio St Chicago IL
Fully refundableReserve now, pay when you stay
The price is £79 per night from 16 Feb to 17 Feb
£79
16 Feb - 17 Feb
includes taxes & fees
8.6/10 Excellent! (2,281 reviews)
Cleanliness, service

Reviewed on 4 Feb 2026

DoubleTree by Hilton Chicago - Magnificent Mile
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 £88 per night from 22 Feb to 23 Feb
£88
22 Feb - 23 Feb
includes taxes & fees
8.4/10 Very Good! (5,634 reviews)
Great Staff Clean Hotel! The heated pool was NOT heated but overall my stay was GREAT

Reviewed on 2 Feb 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 5,075 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

Why should I book my Mayfair holiday with Expedia?
Expedia has you covered for every detail of your next Mayfair holiday. You'll always get the best deal possible, but when you bundle your hotel, flights and/or car hire into a holiday package, you'll save even more. Keen to really make the most of your escape? Add some tours and activities to your customised package. We offer flexible cancellation policies on most bookings, so there's no need to worry if you have to change your plans. Visit our Customer Service Portal link to find out more.
How do I get a cheap holiday to Mayfair?
Lock in flights that fit in with your schedule, add a hotel to your booking and see how much you save with a Mayfair holiday. It's as simple as that! From hotels and flights to hire cars and activities, Expedia is where your cheap getaway begins. And with more than 400 airlines and 321,000 hotel options throughout the world to choose from, you won't be short of choice. Learn more about how you can save money on your next holiday when you book a flight and hotel together with Expedia.
What should I do on my Mayfair holiday?
There's an almost endless list of things to do and see while enjoying a holiday in Mayfair. Portage Park, Walt Disney House, Six Corners and Community First Medical Centre are among this city's best attractions.
Do I need a visa for my Mayfair holiday?
Visa requirements for Mayfair vary based on your nationality and reason for your visit. Be sure to check official government websites to determine if you need a visa for your trip. They'll give you the most up-to-date information, including details about application procedures or any supporting documentation that might be necessary. Enquire about your visa requirements well ahead of time to ensure a smooth travel experience. Finally, double-check to see that your passport has at least six months validity from your planned return date.
What should I wear on my Mayfair holiday?
Consider the sorts of activities you have planned during your Mayfair holiday and choose versatile pieces that you can mix and match. For fashion inspiration or even information on dress codes, browse a few style blogs or social media accounts.
What does an Expedia Mayfair holiday include?
Hotels, flights and a reliable car for your road trip adventures. Simply mix and match your favourite bundle and gain access to great discounts. Once you've made your booking, add on a few sightseeing tours and watch your savings pile up. When it comes to creating your Mayfair holiday, you're the boss! Explore a variety of styles on Expedia and discover the perfect one for you and your guests. From the most popular property types, like apartments and private holiday homes, to many other options, you'll find plenty of holiday rentals in Mayfair to select from so you can plan your adventure just the way you like it.
Does Expedia offer Book Now, Pay Later Mayfair holidays?
Expedia has joined forces with online lender Klarna to make booking your next break a bit easier on the wallet. Paying by instalment means you can spread the costs of your next big holiday, leaving you with more money to spend while you're away. Klarna has several payment plans to choose from, so you're sure to find one that suits your budget. Consider these flexible payment options:

  • Pay monthly holidays: If paying across multiple transactions sounds best for you, Klarna offers just that! Paying in multiple instalments will make that dream getaway possible.
  • No-deposit holidays: When you want to jump on an awesome deal but your budget doesn't quite cover it yet, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to get what you want.

Can I choose my airline with a Mayfair Expedia holiday?
Yes — that's the beauty of an Expedia holiday package. You're in control. We have access to more than 400 airline partners around the world, so you have lots of choice when organising your Mayfair adventure.

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

4.5/5(40 reviews)

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

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

4.5/5(14 reviews)

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 featuring a sunset and rides

Navy Pier

4/5(125 reviews)

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

Navy Pier

Things to do

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Flyover in Chicago

Flyover in Chicago

£28
per adult
98% of travellers recommend
Flyover in Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
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. Flight-inclusive packages are ATOL protected.