Title: Upper East Side Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $690 Expedia.ca

[Hotels in Upper East Side](https://expedia.ca/Upper-East-Side-Milwaukee-Hotels.0-n553248635976481563-0.Travel-Guide-Filter-Hotels)[Flights to Milwaukee](https://expedia.ca/Cheap-Flights-To-Milwaukee.d602647.Travel-Guide-Flights)[Things to do in Milwaukee](https://expedia.ca/Things-To-Do-In-Milwaukee.d602647.Travel-Guide-Activities)[Upper East Side Car Rentals](https://expedia.ca/Car-Rentals-In-Upper-East-Side.d553248635976481563.Car-Rental-Guide)

![](https://images.trvl-media.com/place/553248635976481563/05e24521-643f-40d7-932c-6e2349d952ae.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Upper East Side Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
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Better together  
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- ###  
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Plan, book, and manage your trip all in one place

## Top Holiday Package Deals in Upper East Side

Price found within the past 48 hours. Click for updated prices.

![Home2 Suites by Hilton Milwaukee Downtown](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651130/449092f1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Home2 Suites by Hilton Milwaukee Downtown

Downtown Milwaukee

CA $690

per person

Apr 13 - Apr 15

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Milwaukee (MKE)

8.6/10 Excellent! (968 reviews)

They location was great, the room specious and breakfast was of high quality.

Reviewed on Mar 5, 2026

![Fairfield Inn & Suites by Marriott Milwaukee Downtown](https://images.trvl-media.com/lodging/1000000/80000/79800/79771/d678c17f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Fairfield Inn & Suites by Marriott Milwaukee Downtown

Westown

CA $994

per person

Apr 12 - Apr 15

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Milwaukee (MKE)

8.4/10 Very Good! (1,004 reviews)

Staff were very friendly. Rooms were clean.

Reviewed on Feb 28, 2026

![The Pfister Hotel](https://images.trvl-media.com/lodging/1000000/20000/19500/19467/169f18e6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Pfister Hotel

Downtown Milwaukee

CA $773

per person

Apr 13 - Apr 15

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Milwaukee (MKE)

9.6/10 Exceptional! (2,039 reviews)

Employees were phenomenal! The room was perfect for me and my sister and definitely coming back!

Reviewed on Mar 11, 2026

![Holiday Inn Express Milwaukee Downtown by IHG](https://images.trvl-media.com/lodging/58000000/57140000/57132500/57132464/cf4024e5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Holiday Inn Express Milwaukee Downtown by IHG

Downtown Milwaukee

CA $792

per person

Apr 13 - Apr 15

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Milwaukee (MKE)

9/10 Wonderful! (1,000 reviews)

Breakfast was good, coffee was good, room was clean and spacious, showerhead was perfect.

Reviewed on Mar 6, 2026

![Hampton Inn & Suites Milwaukee Downtown](https://images.trvl-media.com/lodging/1000000/470000/463900/463898/1a6e9416_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hampton Inn & Suites Milwaukee Downtown

Westown

CA $1,039

per person

Apr 12 - Apr 15

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Milwaukee (MKE)

6.6/10 (1,001 reviews)

Not a large selection for breakfast. Standard eggs potatoes waffle maker oatmeal and cereals.. no microwave in room. Microwave in lobby wasn’t so clean. But not over priced and staff was farely friendly. The maintenance man was really nice toilet clogged and he came like 2 minutes later to fix it and had housekeeping there to clean up immediately. Overall good experience and I would stay again.

Reviewed on Mar 10, 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](https://expedia.ca/Milwaukee-Upper-East-Side.dx553248635976481563)

![Downtown skyline with Buildings along the Milwaukee River, in Milwaukee, Wisconsin.; Shutterstock ID 523595590](https://images.trvl-media.com/place/6059651/1182062a-a02d-493d-b9fe-49d298b5def0.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Downtown Milwaukee

 Central business district with cultural, financial, and historical landmarks, Downtown Milwaukee offers shopping at The Shops of Grand Avenue, art galleries in the Historic Third Ward, high-end dining, and vibrant nightlife. Explore the Milwaukee Public Market and Riverwalk, or hop on the free streetcar system. 

[Find hotel + flight trips in Downtown Milwaukee](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Milwaukee&DestID=6059651&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![96144781](https://images.trvl-media.com/place/6059657/3d426080-e9b2-426a-9651-cd836ecf4e89.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Wauwatosa

 Wauwatosa is known for its abundant dining options, and you can plan a trip to Mayfair Mall and The Mayfair Collection while you're in town. 

[Find hotel + flight trips in Wauwatosa](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Wauwatosa&DestID=6059657&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Milwaukee Art Museum](https://images.trvl-media.com/place/6068277/f9df43ae-9037-4ed0-8755-204129016a40.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### East Town

4.5/5(18 area reviews)

 East Town is highly notable for its fantastic nightlife, and you might want to visit top sights like Lake Michigan and Veteran's Park. See more of Milwaukee by jumping on the metro at Michigan & Jackson Tram Stop or Clybourn & Jefferson Tram Stop. 

[Find hotel + flight trips in East Town](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=East%20Town&DestID=6338567&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Ferris Wheel Spinning Round Illuminated in Night Sky](https://images.trvl-media.com/place/7685/c9ddb0cf-39d4-4515-b334-9d7a3f73ea61.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### 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 hotel + flight trips in West Allis](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=West%20Allis&DestID=7685&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![The Milwaukee Riverwalk System began in 1993, as a means to offer public access to the river.  Once complete, the Riverwalk will extend 3.1 miles along both sides of the Milwaukee River, from the site of the former North Avenue Dam, through Downtown and the Historic Third Ward to Lake Michigan.

#LikeALocal](https://images.trvl-media.com/place/2325/e14aea82-f689-465b-a1de-58418a74a9ab.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Westown

2 out of top 10 points of interest in this area

4/5(8 area reviews)

 While visiting Westown, you might make a stop by sights like Miller High Life Theatre and UW–Milwaukee Panther Arena. 

[Find hotel + flight trips in Westown](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Westown&DestID=553248635976470851&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## Upper East Side Hotel Deals

![The Pfister Hotel](https://images.trvl-media.com/lodging/1000000/20000/19500/19467/169f18e6_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Pfister Hotel

424 E Wisconsin Ave Milwaukee WI

Fully refundableReserve now, pay when you stay

CA $204

CA $240 total

Apr 6 - Apr 7

includes taxes & fees

9.6/10 Exceptional! (2,016 reviews)

Employees were phenomenal! The room was perfect for me and my sister and definitely coming back!

Reviewed on Mar 11, 2026

[](https://expedia.ca/Hotel-Search?startDate=06%2F04%2F2026&endDate=07%2F04%2F2026&selected=19467&PinnedHotelID=19467&HadPinnedHotel=true&regionId=553248635976481563)

![Saint Kate - The Arts Hotel](https://images.trvl-media.com/lodging/1000000/30000/23300/23253/3a9f7f5d_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Saint Kate - The Arts Hotel

139 E Kilbourn Ave Milwaukee WI

Fully refundableReserve now, pay when you stay

CA $173

CA $204 total

Mar 29 - Mar 30

includes taxes & fees

9.8/10 Exceptional! (2,576 reviews)

Our room (706) was particularly spacious and had a lovely chaise for reading.

Reviewed on Mar 12, 2026

[](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=23253&PinnedHotelID=23253&HadPinnedHotel=true&regionId=553248635976481563)

![The Knickerbocker on the Lake](https://images.trvl-media.com/lodging/1000000/890000/889400/889344/0f2f3dc7_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Knickerbocker on the Lake

1028 East Juneau Avenue Milwaukee WI

Fully refundableReserve now, pay when you stay

CA $126

CA $149 total

Mar 26 - Mar 27

includes taxes & fees

8.6/10 Excellent! (1,013 reviews)

This is a lovely historic hotel close to the art and theatre district. Out room was clean but really needed an update. I understand it’s historic, but there were some soft spots on the floor in a couple of spots that were uncomfortable. The water in the shower was very touchy and unpredictable between ...

Reviewed on Mar 9, 2026

[](https://expedia.ca/Hotel-Search?startDate=26%2F03%2F2026&endDate=27%2F03%2F2026&selected=889344&PinnedHotelID=889344&HadPinnedHotel=true&regionId=553248635976481563)

[See all 1,123 properties in Upper East Side](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=13%2F03%2F2026&endDate=14%2F03%2F2026&regionId=553248635976481563)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

## Frequently asked questions

### How much does an Upper East Side vacation package cost?

### How do I get a cheap travel package to Upper East Side?

### Where should I stay in Upper East Side?

### What are the top hotels in Upper East Side?

### How far in advance should I book my Upper East Side vacation?

### What does an Expedia Upper East Side travel package include?

### What should I know before booking an Upper East Side travel package?

### Can I choose my airline with an Upper East Side Expedia vacation package?

### If I'm not able to travel, can I cancel my Upper East Side vacation package?

### Discover the most popular places to visit in Upper East Side

![Harley-Davidson Museum featuring interior views](https://images.trvl-media.com/place/6279040/52cab404-1cac-4be9-bd03-910682810f03.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Harley-Davidson Museum

Delve into the history of one of the world’s most famous motorcycle brands via interactive exhibits, photo galleries, workshops and behind-the-scenes tours.

[](https://expedia.ca/Harley-Davidson-Museum-Menomonee-River-Valley.d6279040.Vacation-Attraction)

![Milwaukee Art Museum](https://images.trvl-media.com/place/6068277/1fe18a15-7f30-4ecc-8164-b72f9b7fcfed.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Milwaukee Art Museum

Peruse a vast collection of classic European and American art in this gallery that is housed in a striking modern building.

[](https://expedia.ca/Milwaukee-Art-Museum-East-Town.d6068277.Vacation-Attraction)

#### Potawatomi Bingo Casino

Why not roll the dice with a visit to Potawatomi Bingo Casino during your time in Milwaukee? Attend a sporting event or simply enjoy the lively breweries while you're in the area. 

[](https://expedia.ca/Potawatomi-Bingo-Casino-Menomonee-River-Valley.d6335076.Vacation-Attraction)

### Things to do

![2 Hour Milwaukee Scavenger Hunt Game](https://mediaim.expedia.com/localexpert/49296611/4017c436-a1bb-44c8-9945-447fa08e21b1.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Milwaukee Scavenger Hunt Walking Tour and Game

CA $67

per adult

[](https://expedia.ca/things-to-do/milwaukee-scavenger-hunt-walking-tour-and-game.a49296611.activity-details)

[See all activities in Milwaukee](https://expedia.ca/things-to-do/search?rid=553248635976481563)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.