A Travel Price Comparison for United States of America Portland, Maine vs. Milwaukee for Food, Nightlife, Families, and Couples

Should you visit Portland, Maine or Milwaukee?

Which is cheaper to visit? Which is more expensive for vacation?

Should I visit Portland, Maine or Milwaukee? This is a common question asked by many travelers. By figuring out which city has activities that align with your interests along with knowing which is more affordable, you'll understand where you can get more bang for your buck. So, let's dive into the details and the data, which all comes from actual travelers.

Portland, Maine

Portland, Maine is a scenic, picturesque, and seaside coastal town. The beauty of this spot is also one of the main reasons why visitors come. Visitors also love the nightlife, food, and beaches.

Milwaukee

Milwaukee is a undiscovered, friendly, and welcoming city. Other popular activities here include museums, nightlife, and shopping.

Portland, Maine and Milwaukee: Pros and Cons

Pros
  • Active nightlife
  • Popular beach
  • Good for hiking
  • Popular at Christmas
  • Family-friendly
  • Good for couples and romance
  • Impressive beauty
Things to Consider
  • Less popular with backpackers
Pros
  • Popular museums and historical sights
  • Active nightlife
  • Family-friendly
  • Good for students
Things to Consider
  • Less popular with couples
  • Less popular with backpackers


Is there more to do in Portland, Maine or Milwaukee?

Travelers will generally find more things to do in Portland, Maine than Milwaukee. While Milwaukee is larger than Portland, Maine, Portland, Maine has more sights and attractions for tourists. Portland, Maine is more popular for its food, beaches, hiking, and impressive beauty, while Milwaukee is known for its museums. Portland, Maine is more touristy than Milwaukee and is popular for its seafood restaurants, scenic lighthouse, and coastal walks. It is also home to The Portland Head Light. Milwaukee is popular for its many breweries and its baseball culture.

How is Portland, Maine different from Milwaukee?

Which is Better for a Holiday?

Let's take a look at the differences and similarities between Milwaukee and Portland, Maine. Then, you can decide for yourself which place is better for your next trip.

Are the Museums and Historical Sights Better in Portland, Maine or Milwaukee?

Portland, Maine
Milwaukee

Milwaukee is a popular place for its museums and landmarks. However, Portland, Maine does not have museums and landmarks.

If you're looking for an educational opportunity, there are a decent number of museums and historical sights around Milwaukee. There are several unique museums like the Harley-Davidson Museum, the National Bobblehead Hall of Fame and Museum, and the Milwaukee Public Museum. There's also the Milwaukee Art Museum and the Grohmann Museum as well as outdoor sculpture parks and other cultural and historic museums.

Portland, Maine does not have museums and landmarks.


Is the Food Better in Portland, Maine or Milwaukee? Which Destination has the Best Restaurants?

Portland, Maine
Milwaukee

Portland, Maine is a coastal town with good options for its restaurants. However, Milwaukee is lacking in options for its restaurant scene.

Portland, Maine has a delicious restaurant scene that relies on local flavors. The town has grown into a foodie destination that takes advantage of its waterfront setting. Many restaurants make use of the fresh seafood with lobster rolls and oysters on the half shell being popular. You'll also find a lot of dishes that use haddock and whole lobsters.

Milwaukee may not make the list for most foodies, but you'll find what you need while you're in town. The Midwest is known for its artery clogging comfort foods, and Milwaukee is no exception. Cheese curds, fried fish, fruit dumplings, and frozen custard are all popular.

Is Portland, Maine or Milwaukee Better for Nightlife?

Portland, Maine
Milwaukee

Party-goers will find similar levels of energy in Portland, Maine and Milwaukee.

Portland, Maine has an active nightlife scene for those who seek it out. The city has many microbreweries, wine bars, taverns, and pubs. You'll find many places concentrated in the Old Port, which has a charming and fun atmosphere.

If you're looking for night time activities Milwaukee has a few options to choose from. You'll find a decent number of breweries around town. There are also wine bars, nightclubs, and live music venues that are worth checking out.

Is Portland, Maine or Milwaukee Better for Beaches?

Portland, Maine
Milwaukee

Portland, Maine is an excellent place to visit for the beache. However, Milwaukee is not a beach destination.

The beaches at Portland, Maine attract visitors from all over. It has many sandy and calm beaches. The water may be too cold to swim, but the beaches are perfect for flying a kite or hanging out with family.

Milwaukee is not a beach destination.


Is Portland, Maine or Milwaukee Better for Hiking?

Portland, Maine
Milwaukee

Portland, Maine is a coastal town with good options for its hiking trails. However, Milwaukee is not a hiking destination.

Plenty of visitors go hiking around Portland, Maine. In addition to bike trails, there are several good hikes in the area.

Milwaukee is not a hiking destination.

Is the Shopping Better in Portland, Maine or Milwaukee?

Portland, Maine
Milwaukee

Shopping is a popular activity in both Milwaukee and Portland, Maine.

Many visitors go to Portland, Maine to go shopping. The town has many nice local boutiques to explore. Head downtown for the best local venues and the most interesting shopping opportunities.

Plenty of visitors enjoy shopping while in Milwaukee. You'll find the standard shopping centers and shopping malls around town, but if you want some more local vendors, check out the areas around the Historic Third Ward and The Village in Wauwatosa.

Is Portland, Maine or Milwaukee Better for Christmas?

Portland, Maine
Milwaukee

Portland, Maine is a decent place to visit for its Christmas holiday experiences. However, Milwaukee does not offer Christmas activities.

The Christmas holiday can be fun in Portland, Maine. Watch the Christmas tree lighting or listen to the symphony at Christmas time.

Milwaukee does not offer Christmas activities.


Is Portland, Maine or Milwaukee Better for Families?

Portland, Maine
Milwaukee

Kids will enjoy a visit to either Portland, Maine or Milwaukee.

You'll find plenty of kid-friendly things to do in Portland, Maine. It is a charming town with a number of kid-friendly museums, walks, and waterfront activities. You can visit the Portland Observatory, Bug Light Park, or grab ice cream in the Old Port. There are also children's museums such as the Children's Museum & Theatre of Maine.

Milwaukee offers lots of family activities. Kids will enjoy a visit to Discovery World, which is a science center with hands-on exhibits. There's also the Milwaukee County Zoo and the Milwaukee Public Museum. Younger kids will also enjoy a stop at Betty Brinn Children's Museum.

Is Portland, Maine or Milwaukee Better for Couples?

Portland, Maine
Milwaukee

Portland, Maine is a coastal town with good options for its romantic activities. However, Milwaukee is lacking in options for couples.

Portland, Maine makes for a fun place to visit for a couple. Couples will enjoy the beautiful waterfront setting, the fine dining restaurants, and everything that the city has to offer. Head to the Old Port for romantic restaurants and a great atmosphere or catch a show at Portland Stage.

Milwaukee is not always the best place to visit for a couple. Take a walk or visit a local restaurant. There are also museums and performances that make for a nice outing.

Is Portland, Maine or Milwaukee Better for Students?

Portland, Maine
Milwaukee

Milwaukee is a popular place for students. However, Portland, Maine is not popular with students.

Milwaukee is popular with students. It's home to a number of colleges and universities, so there is a bit of a college town vibe.

Portland, Maine is not popular with students.


Is Portland, Maine or Milwaukee Better for Public Transit? Which Is Easier to Get Around Without a Car?

Portland, Maine
Milwaukee

Milwaukee is a city with a few options for its public transit. However, Portland, Maine is not particularly known for times when you don't have a car.

Public transit is generally limited in Milwaukee. There are buses that travel around town.

Public transit is quite limited in Portland, Maine. There is a very basic bus system but you really must have a car to explore the city.

Is Portland, Maine or Milwaukee a more walkable city?

Portland, Maine
Milwaukee

Milwaukee is a popular place for its ease of walking around. However, Portland, Maine is not particularly known for its walkability.

Milwaukee is a somewhat walkable city. Parts of the city are relatively compact and walkable. The most walkable neighborhoods are East Side, Riverwest, Brewers Hill, Downtown, Avenues West/Marquette, Third Ward, Walker's Point, and Bay View.

Portland, Maine is generally not a very walkable coastal town. Downtown is very walkable but if you want to travel to other areas you'll need a car.

For even more information, also check out Is Portland, Maine Worth Visiting? and Is Milwaukee Worth Visiting?.

Should I spend more time in Milwaukee or Portland, Maine?

How long in Portland, Maine or Milwaukee?

You'll be able to find lots of things to do in Portland, Maine or Milwaukee to fill your time. Many travelers usually spend more of their time in Portland, Maine than Milwaukee because of the number of activities and things to do in the area. Usually, 2-3 days is a good amount of time for Portland, Maine, and 1-2 days is enough time in Milwaukee.

Families should spend more time in Portland, Maine than Milwaukee. Because of the many family-friendly attractions and fun things to do for kids in Portland, Maine, it's a great place to visit with the whole family.

Couples should spend more time in Portland, Maine than Milwaukee. You'll find plenty of romantic sights and fun activities in Portland, Maine that are great for a weekend getaway or a longer couple's trip.

Backpackers and budget travelers should spend more time in Milwaukee than Portland, Maine if your budget allows for it. With a larger number of budget-friendly sights, good nightlife, and active things to do, anyone traveling on a budget would have a good time in Milwaukee.


  • How many days in Portland, Maine or Milwaukee? Ideal Length of Stay
    Portland, Maine 2-3 
    Milwaukee 1-2

One day in Portland, Maine or Milwaukee?

You'll find food and shopping around the coastal town of Portland, Maine. Many visitors spend time at the beach while visiting the area. Since there is so much to do in the area, one day is probably not enough for all of it. It has many unique tourist attractions and fascinating things to do.

The friendly destination of Milwaukee offers shopping and museums. Take your pick from the many activities offered here. One day is usually enough time to experience most activities.


A weekend in Portland, Maine or Milwaukee?

You'll find shopping and nightlife around the scenic destination of Portland, Maine. People usually spend lots of time at the beach. This is a popular place to visit for a weekend.A weekend should give you a good understanding of everything this coastal town has to offer. This coastal town offers a variety of activities to choose from.

The city of Milwaukee offers museums and nightlife. A weekend here is typical. The entire region has so many activities, and you'll want time to do everything. A weekend is often enough time to do most activities.

Five days in Portland, Maine or Milwaukee?

Travelers enjoy the nightlife and food when visiting the picturesque coastal town of Portland, Maine. The length of your ideal trip is an individual decision. It's also a great beach destination, too. Five days is plenty of time to see everything, even with extra days to spare.

Milwaukee is a great place to explore. This city offers something for everyone. Most people find that five days is more than enough time to see everything.

A week in Portland, Maine or Milwaukee?

Portland, Maine is a popular choice for travelers. It's a great spot for a beach vacation. One week is usually plenty of time to spend here with extra days to spare. With this much time, visitors often visit nearby destinations or take day trips. It will give you the chance to have new experiences.

Many people enjoy the shopping and museums when visiting Milwaukee. The length of your trip often depends on your style of travel. One week is plenty of time to see everything, even with extra days to spare.


For some great organized tour ideas, see The Best 10-Day Tours in United States of America, The Best One Week (7-Day) Tours in United States of America, The Best 2-Week Tours in United States of America, and The Best 3-Week Tours in United States of America.


Which place is cheaper, Milwaukee or Portland, Maine?

These are the overall average travel costs for the two destinations.

The average daily cost (per person) in Portland, Maine is $192, while the average daily cost in Milwaukee is $176. These costs include accommodation (assuming double occupancy, so the traveler is sharing the room), food, transportation, and entertainment. While every person is different, these costs are an average of past travelers in each destination. What follows is a categorical breakdown of travel costs for Portland, Maine and Milwaukee in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Portland, Maine $115
    Milwaukee $99
  • Accommodation Typical double-occupancy room
    Portland, Maine $230
    Milwaukee $198
Compare Hotels in Portland, Maine and Milwaukee

Looking for a hotel in Portland, Maine or Milwaukee? Prices vary by location, date, season, and the level of luxury. See below for options and compare which is best for your budget and travel style.

Hotels in Portland, Maine


Hotels in Milwaukee


Kayak helps you find the best prices for hotels, flights, and rental cars for destinations around the world. Compare prices for multiple destinations when planning your next trip.


Our Analysis
We've analyzed the average and typical hotel prices based on guest reviews, star ratings, and hotel amenities here: Portland, Maine Hotel Prices and Milwaukee Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Portland, Maine $34
    Milwaukee $38

Is it cheaper to fly into Portland, Maine or Milwaukee?

Prices for flights to both Milwaukee and Portland, Maine change regularly based on dates and travel demand. We suggest you find the best prices for your next trip on Kayak, because you can compare the cost of flights across multiple airlines for your prefered dates.





Food
  • Food Meals for one day
    Portland, Maine $48
    Milwaukee $52
Typical Food Prices in Portland, Maine

Below are a few samples from actual travelers for food and meal costs in Portland, Maine:


  • Breakfast for 2
    $17
  • Dinner for 2
    $30

Food Tours and Cooking Classes in Milwaukee

For Milwaukee, here are some samples of tours and activities related to meals and dining experiences:

  • Family Fun Food Tour: $80
  • Local Food Tour: $97
  • Milwaukee Walking Food Tour With Secret Food Tours: $99
  • Original Milwaukee Guided Brewery Tour with Lunch or Dinner: $139

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Portland, Maine $39
    Milwaukee $26

Tours and Activities in Portland, Maine

Here are a few actual costs in Portland, Maine for available activities, ticket prices, and tours:

  • 2 Hours | Portland, Maine Black History Walking Tour: $49
  • 2 Hours | Portland, Maine Hidden Histories Walking Tour: $49
  • A Walk Through Time Tour in Portland: $49
  • Around The Peninsula Bike Tour: $79
  • Audio Guided Walking Tour from Old Port of Portland, Maine: $6.75
  • Casco Bay Half-Day Sea Kayak Tour: $75
  • Central Coastal Maine Private Day Tour: $250
  • Discover Portland City and Lighthouse Tour: $48
  • Donut Tasting Walking Tour in Portland’s Old Port: $48
  • Downtown Portland In-App Audio Tour (ENG): $9.00
  • Downtown Portland, Maine City and Lighthouse Tour-2.5 hour Land Tour: $70
  • Guided RIB Boat Adventure of Casco Bay: $75

Tours and Activities in Milwaukee

For Milwaukee, here are a few prices for actual activities, tours, and tickets provided by various companies:

  • Skip the Line: Museum Admission Ticket - Grohmann Museum: $5.00
  • The Grand Milwaukee Walk: A Self-Guided Audio Tour: $6.99
  • The Grand Walk: A Self-Guided Audio Tour through Milwaukee: $6.99
  • Unique Scavenger Hunt Experience in Milwaukee by Operation City Quest: $10
  • Geneva Lake Shore Path: Uncover 21 miles of stories on a self-guided audio tour: $10
  • Milwaukee Brewers Baseball Game Ticket at American Family Field: $11
  • Skip The Line: Harley-Davidson Museum Admission Ticket with Audio Guided Option: $22
  • Macabre Milwaukee Walking Tour: $26
  • Shakers Original Historical Ghost Tour: $27
  • Downtown Kenosha Urban Art and Photography Walking Tour: $30
  • Brew City Ghosts: Macabre Milwaukee By US Ghost Adventures: $30
  • Milwaukee Private or Public Pedal Tavern Tour : $35

Alcohol
  • Alcohol Drinks for one day
    Portland, Maine $24
    Milwaukee $33

Sample the Local Flavors in Portland, Maine

Here are a few nightlife and alcohol tours and activities from local tour providers in Portland, Maine:

  • Old Port Brewery & Pub Walking Tour: $89
  • Local Brewery & Spirits Bus Tour: $99

Sample the Local Flavors in Milwaukee

Also in Milwaukee, these are the prices for nightlife and alcohol related activities from various tour providers:

  • Sip of Milwaukee Guided Brewery Tour with Snack: $99


When comparing the travel costs between Portland, Maine and Milwaukee, we can see that Portland, Maine is more expensive. However, the two cities are actually relatively comparable in price, as the difference is somewhat minimal. Generally, this means that you could travel with generally the same travel style and level of luxury in each place. Since both cities are in North America, it's no surprise that their costs are relatively close, as many destinations here have somewhat similar travel prices overall.

If you're trying to decide if either of these two destinations are within your price range, also see Is Portland, Maine Expensive? and Is Milwaukee Expensive?.


Which is Bigger, Portland, Maine or Milwaukee?

Milwaukee has a larger population, and is about 9 times larger than the population of Portland, Maine. When comparing the sizes of Portland, Maine and Milwaukee, keep in mind that a larger population does not always imply the destination has more attractions or better activities. So, always research the type of place that you want to visit along with the activities and attractions that interest you.


When is the best time to visit Portland, Maine or Milwaukee?

Both places have a temperate climate with four distinct seasons. As both cities are in the northern hemisphere, summer is in July and winter is in January.

Should I visit Portland, Maine or Milwaukee in the Summer?

The summer brings many poeple to Portland, Maine as well as Milwaukee. Many visitors come to Portland, Maine in the summer for the beaches, the hiking, and the family-friendly experiences. Also, most visitors come to Milwaukee for the family-friendly experiences during these months.

In July, Portland, Maine is generally cooler than Milwaukee. Daily temperatures in Portland, Maine average around 69°F (20°C), and Milwaukee fluctuates around 74°F (23°C).

The sun comes out a lot this time of the year in Milwaukee. People are often attracted to the plentiful sunshine in Portland, Maine this time of the year. In the summer, Portland, Maine often gets less sunshine than Milwaukee. Portland, Maine gets 282 hours of sunny skies this time of year, while Milwaukee receives 321 hours of full sun.

Portland, Maine usually gets less rain in July than Milwaukee. Portland, Maine gets 2.6 inches (66 mm) of rain, while Milwaukee receives 3.4 inches (87 mm) of rain this time of the year.


  • Summer Average Temperatures July
    Portland, Maine 69°F (20°C) 
    Milwaukee 74°F (23°C)

Should I visit Portland, Maine or Milwaukee in the Autumn?

Both Milwaukee and Portland, Maine are popular destinations to visit in the autumn with plenty of activities. Most visitors come to Portland, Maine for the hiking trails, the shopping scene, and the natural beauty of the area during these months. Also, the autumn months attract visitors to Milwaukee because of the shopping scene.

Portland, Maine is cooler than Milwaukee in the autumn. The daily temperature in Portland, Maine averages around 49°F (9°C) in October, and Milwaukee fluctuates around 53°F (12°C).

Portland, Maine usually receives more sunshine than Milwaukee during autumn. Portland, Maine gets 196 hours of sunny skies, while Milwaukee receives 174 hours of full sun in the autumn.

In October, Portland, Maine usually receives more rain than Milwaukee. Portland, Maine gets 3.3 inches (84 mm) of rain, while Milwaukee receives 2 inches (50 mm) of rain each month for the autumn.


  • Autumn Average Temperatures October
    Portland, Maine 49°F (9°C) 
    Milwaukee 53°F (12°C)

Should I visit Portland, Maine or Milwaukee in the Winter?

Both Milwaukee and Portland, Maine during the winter are popular places to visit. The winter months attract visitors to Portland, Maine because of the Christmas ambience, the shopping scene, and the cuisine. Furthermore, the museums, the shopping scene, and the cuisine are the main draw to Milwaukee this time of year.

It's quite cold in Milwaukee in the winter. The weather in Portland, Maine can be very cold. In the winter, Portland, Maine is around the same temperature as Milwaukee. Typically, the winter temperatures in Portland, Maine in January average around 21°F (-6°C), and Milwaukee averages at about 21°F (-6°C).

In the winter, Portland, Maine often gets more sunshine than Milwaukee. Portland, Maine gets 163 hours of sunny skies this time of year, while Milwaukee receives 138 hours of full sun.

Portland, Maine usually gets more rain in January than Milwaukee. Portland, Maine gets 3.4 inches (86 mm) of rain, while Milwaukee receives 1.6 inches (41 mm) of rain this time of the year.


  • Winter Average Temperatures January
    Portland, Maine 21°F (-6°C) 
    Milwaukee 21°F (-6°C)

Should I visit Portland, Maine or Milwaukee in the Spring?

The spring attracts plenty of travelers to both Portland, Maine and Milwaukee. The beaches and the natural beauty are the main draw to Portland, Maine this time of year.

In April, Portland, Maine is generally cooler than Milwaukee. Daily temperatures in Portland, Maine average around 43°F (6°C), and Milwaukee fluctuates around 47°F (8°C).

People are often attracted to the plentiful sunshine in Milwaukee this time of the year. In Portland, Maine, it's very sunny this time of the year. Portland, Maine usually receives around the same amount of sunshine as Milwaukee during spring. Portland, Maine gets 212 hours of sunny skies, while Milwaukee receives 211 hours of full sun in the spring.

In April, Portland, Maine usually receives more rain than Milwaukee. Portland, Maine gets 3.3 inches (85 mm) of rain, while Milwaukee receives 2.8 inches (70 mm) of rain each month for the spring.


  • Spring Average Temperatures April
    Portland, Maine 43°F (6°C) 
    Milwaukee 47°F (8°C)

Typical Weather for Milwaukee and Portland, Maine

Portland, Maine Milwaukee
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 21°F (-6°C) 3.4 inches (86 mm) 21°F (-6°C) 1.6 inches (41 mm)
Feb 24°F (-5°C) 3.5 inches (89 mm) 26°F (-4°C) 1.1 inches (29 mm)
Mar 33°F (1°C) 3.6 inches (91 mm) 36°F (2°C) 2.2 inches (57 mm)
Apr 43°F (6°C) 3.3 inches (85 mm) 47°F (8°C) 2.8 inches (70 mm)
May 53°F (12°C) 3.3 inches (85 mm) 58°F (14°C) 2.9 inches (73 mm)
Jun 63°F (17°C) 3.1 inches (79 mm) 68°F (20°C) 3.6 inches (91 mm)
Jul 69°F (20°C) 2.6 inches (66 mm) 74°F (23°C) 3.4 inches (87 mm)
Aug 67°F (20°C) 2.6 inches (66 mm) 72°F (22°C) 2.7 inches (68 mm)
Sep 59°F (15°C) 3.1 inches (78 mm) 65°F (18°C) 3 inches (77 mm)
Oct 49°F (9°C) 3.3 inches (84 mm) 53°F (12°C) 2 inches (50 mm)
Nov 39°F (4°C) 4.8 inches (123 mm) 41°F (5°C) 2 inches (51 mm)
Dec 27°F (-3°C) 4.1 inches (103 mm) 27°F (-3°C) 1.7 inches (44 mm)