Upper East Side Holidays from £1,722

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Your Upper East Side Holiday

Our Upper East Side holiday packages are a speedy and practical way to organise and book your next escape. Experience the magic of this unique neighbourhood without the hassle of organising it all yourself. When it's time to explore the sights, you'll find loads of top attractions nearby including Milwaukee Art Museum, Discovery World and Charles Allis Art Museum. Visit one or all during your trip to Upper East Side. Stop dreaming and start doing. When you're ready to book your next holiday to Upper East Side, Expedia will help you get there.

Price found within the past 48 hours. Click for updated prices.
Doubletree by Hilton Pleasant Prairie Kenosha

Doubletree by Hilton Pleasant Prairie Kenosha

£1,722
per person
25 Nov - 2 Dec
found 8 hours ago
Return flight included
London (LHR) to Milwaukee (MKE)
8.8/10 Excellent! (1,002 reviews)
Would definitely stay here again!

Reviewed on 8 Oct 2026

Where to stay in Upper East Side

Find the best Upper East Side areas and neighborhoods for the activities you enjoy most. Learn more about Upper East Side
A river with a city skyline, including a tall building with a pointed roof, and a park with yellow trees.

Downtown Milwaukee

Lake Michigan and Cathedral Square are a few top attractions in Downtown Milwaukee. Hop around the city on the metro at Michigan & Jackson Tram Stop or Clybourn & Jefferson Tram Stop and check out the area's fantastic nightlife, stunning river views and acclaimed art galleries.

Find hotels in Downtown Milwaukee
A stone bridge with a wooden walkway surrounded by lush greenery.

Wauwatosa

1 out of top 10 points of interest in this area

Travellers come to Wauwatosa for its abundant dining options, and you can see top attractions like Mayfair Mall and The Mayfair Collection while you're in town.

Find hotels in Wauwatosa
A river with buildings reflecting on the water, a bridge, and a tall building with a green roof.

West Allis

West Allis is noteworthy for its restaurants, and you can make a stop at top attractions like Milwaukee Mile Speedway and Wisconsin State Fair Park.

Find hotels in West Allis
A river with boats, a marina, and historic buildings along the waterfront.

Historic Third Ward

Experience Milwaukee’s hot spot for art and fashion when you check out the dynamic boutiques, restaurants, theaters and galleries that fill this exciting district.

Find hotels in Historic Third Ward
A pedestrian bridge over a river with a city skyline in the background, including a prominent bank building.

East Town

Lake Michigan and Cathedral Square are top sights in East Town, and you should be sure to explore the fantastic nightlife. Hop aboard the metro at Michigan & Jackson Tram Stop or Clybourn & Jefferson Tram Stop to see more sights in the area.

Find hotels in East Town

Top hotels in Upper East Side

Hyatt Regency Milwaukee

Hyatt Regency Milwaukee

333 W Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
£83
1 Nov - 2 Nov
includes taxes & fees
8.6/10 Excellent! (1,521 reviews)
"Staff were incredibly helpful and kind"

Reviewed on 8 Oct 2026

Hyatt Regency Milwaukee
Sheraton Milwaukee Brookfield Hotel

Sheraton Milwaukee Brookfield Hotel

375 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
£55
8 Nov - 9 Nov
includes taxes & fees
Sheraton Milwaukee Brookfield Hotel
Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown

700 N. Water Street Milwaukee WI
Fully refundableReserve now, pay when you stay
£106
9 Nov - 10 Nov
includes taxes & fees
9.6/10 Exceptional! (2,406 reviews)
"The meals and drink cards are a wonderful perk. Parking can add up, but typical for area"

Reviewed on 8 Oct 2026

Drury Plaza Hotel Milwaukee Downtown
See all 1,133 properties in Upper East Side
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.
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Frequently asked questions

How much does an Upper East Side travel package cost?
Be ready to book, because a trip to Upper East Side starts from an affordable £1,722. When you bundle your flights, hotels and car rentals into a package, you'll walk away with the best prices.
If I'm not able to travel, can I cancel my Upper East Side travel package?
Yes, you can. We understand that even the best-laid plans can go awry, so we're here to help if you need to make changes to your Upper East Side travel package. You may be able to amend or cancel your itinerary at no cost if you've booked in the last 24 hours. Your airline, hotel or car rental company may impose a fee if you booked more than 24 hours ago. Have a look at our Customer Service Portal for more information. Also, check your itinerary for the nitty-gritty on change fees.
How do I get a cheap travel package to Upper East Side?
Imagine all the fun things you could do in Upper East Side with a wad of extra cash in your wallet. Watch your savings stack up when you bundle your hotel and airfare bookings into an Upper East Side travel package. You have plenty of choice when it comes to booking with Expedia too. In fact, you can take your pick of over 550 airlines and 1,000,000 properties worldwide. Whether you're enjoying a break with the entire family or adventuring alone, planning a trip to Upper East Side is better with a package.
Does Expedia offer Book Now, Pay Later Upper East Side holidays?
Expedia has teamed up with online lender Klarna to make booking your next getaway easier on your hip pocket. Paying by instalment means you can spread the costs of your next adventure, leaving you with more cash to spend while you're travelling. Klarna has several payment plans to choose from, so you're sure to find something that fits your budget. Consider these flexible payment options:
  • Pay monthly holidays: Escape on that dream holiday sooner with Klarna's convenient monthly instalment plans. If paying small amounts each month sounds right for you, pick this option at checkout.
  • Pay in instalments holidays: Into the idea of paying off your holiday in multiple transactions? Consider this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: Hitting the "book now" button is easier with this payment plan. Simply put down a small deposit on your holiday and then start packing your suitcase.
Where should I stay in Upper East Side?
A visit to Upper East Side has to include Milwaukee Art Museum and American Family Field. Stay somewhere nearby so you can easily access these impressive sights.
What are the top hotels in Upper East Side?
If this will be your first time in Upper East Side, make a reservation at Hilton Milwaukee City Centre or Hyatt Regency Milwaukee. Both offer friendly service and are popular options with lots of travellers.
How far in advance should I book my Upper East Side holiday?
It's tricky picking the ideal time for airfares, but we generally say the earlier, the better. Most international journeys on Expedia become available up to 12 months in advance. If you're booking at the last minute, fear not. Budget prices occasionally appear within a few weeks of departure dates.
What does an Expedia Upper East Side travel package include?
Select from any combination of rental cars, flights and hotels. Once you've made your booking, you can add the fun stuff like experiences and activities. Want to pick your fare class? That's possible too. The choice is all yours when it comes to planning your perfect Upper East Side escape.
What should I know before booking an Upper East Side travel package?
So many places to explore, so many things to see and do. With a travel package, you'll be able to tick more of them off your list. Combine your hotels, flights and rental cars and see how much you save.
Can I choose my airline with an Upper East Side Expedia travel package?
Expedia offers access to more than 550 partner airlines globally, so you certainly can. Just choose your preferred carrier and craft your ideal Upper East Side trip.

Stay near popular Upper East Side attractions

Miramar Theatre

You can make plans for a show at Miramar Theatre during your trip to Milwaukee.
See properties

Things to do

Grohmann Museum

Skip the Line: Museum Admission Ticket - Grohmann Museum

£4
per adult
Skip the Line: Museum Admission Ticket - Grohmann Museum
Milwaukee Morbid Mirrorlight Ghost Tours

Milwaukee Morbid Mirrorlight Ghost Tours

£19
per adult
Milwaukee Morbid Mirrorlight Ghost Tours
View of E. Wisconsin Ave. looking towards Lake Michigan

Downtown Milwaukee Walking Tour

£12
per adult
Downtown Milwaukee Walking Tour
See all activities in Milwaukee

* 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.