A Travel Price Comparison for United States of America Chicago vs. Milwaukee for Vacations, Tours, and Honeymoons

Should you visit Chicago or Milwaukee?

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

Which city is more affordable and which is best for your travel style? If you're trying to figure out where to go next, comparing the travel costs between Chicago and Milwaukee can help you decide which place is right for you.

Where Should I go: Chicago or Milwaukee?

Chicago

Located in the Midwest, Chicago is the third largest city in the United States. It has a population of almost 3 million and a metropolitan area that covers more than 10,000 square kilometers. It is also a hub for music, comedy and theater. It's skyline is beautiful with modern skyscrapers and Lake Michigan as a backdrop. It is easy to stay entertained in Chicago for weeks. There are world class museums, upscale or eclectic shopping opportunities, and impressive architecture.

Milwaukee

Milwaukee is a city in the U.S. state of Wisconsin on Lake Michigan's western shore. It's known for its breweries, many of which offer tours chronicling its role in the beer industry. Overlooking the Menomonee River, the Harley-Davidson Museum displays classic motorcycles, including one of Elvis Presley's. Nearby is the Milwaukee Public Museum, with its large-scale European Village and a recreation of old Milwaukee. In summertime, festivals let loose by the lake almost every weekend. These attractions along with stylish eating and shopping areas have turned Wisconsin's largest city into an interesting and attractive destination.

Which city is cheaper, Milwaukee or Chicago?

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

The average daily cost (per person) in Chicago is $221, while the average daily cost in Milwaukee is $141. 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 city. What follows is a categorical breakdown of travel costs for Chicago and Milwaukee in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Chicago $152
    Milwaukee $79
  • Accommodation Typical double-occupancy room
    Chicago $304
    Milwaukee $158
Compare Hotels in Chicago and Milwaukee

Looking for a hotel in Chicago 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 Chicago


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.


Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Chicago $29
    Milwaukee $31
Typical Local Transportation prices in Chicago

Here are some examples of typical transportation prices from actual travelers in Chicago:


  • Parking
    $19
  • Taxi Ride
    $10
  • Taxi from Airport
    $45

Hired Cars and Shuttles in Chicago

Some specific examples of transportation prices in Chicago:

  • Transfers in Chicago: $107
  • Transfer to Chicago Premium Outlets: $288
  • Transfer from O'Hare International Airport to Chicago: $93
  • Private transfer: Chicago to Chicago International Airport (MDW): $105
  • Private transfer: Chicago International Airport (MDW) to Chicago: $105
  • Private Transfer: O'Hare International Airport (ORD) to Chicago: $133
  • Private Transfer: Chicago to O'Hare International Airport (ORD): $133
  • Private Transfer from Chicago City to Chicago (ORD) Airport: $113
  • Private Transfer from Chicago City to Chicago (MDW) Airport: $113
  • Private Transfer from Chicago (ORD) Airport to Chicago City: $113
  • Private Transfer from Chicago (MDW) Airport to Chicago City: $113
  • Private Sedan Transfer from Chicago Downtown to O`Hare airport: $100

Hired Cars and Shuttles in Milwaukee

Also for Milwaukee, here are a few examples of actual transportation services:

  • Milwaukee - General Mitchell Airport One Way Transfer: $64
  • Private Transfer Milwaukee Airport MKE to Milwaukee in Business Class Car: $67
  • Private Transfer Milwaukee Airport MKE to Milwaukee in Luxury Class Car: $100
  • Private Transfer Milwaukee Airport MKE to Milwaukee in an SUV: $83
  • Private Transfer Milwaukee to Milwaukee Airport MKE in Business Class Car: $67
  • Private Transfer Milwaukee to Milwaukee Airport MKE in a Luxury Car: $100
  • Private Transfer Milwaukee to Milwaukee Airport MKE in an SUV: $83

Is it cheaper to fly into Chicago or Milwaukee?

Prices for flights to both Milwaukee and Chicago 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
    Chicago $37
    Milwaukee $41
Typical Food prices in Chicago

Below are a few samples from actual travelers for food and meal costs in Chicago:


  • Dinner for 1
    $24
  • Dinner for 3
    $118

Food Tours and Cooking Classes in Chicago

Also, here are some specific examples of food and dining related activities in Chicago.

  • Traveling Spoon Chicago-Style Deep Dish Pizza Private Online Cooking Class: $27
  • Learn to Make Chicago Deep-Dish Pizza with a Local: $49
  • Lonely Planet Experiences: River North Historical Food Tour: $61
  • Private Fusion Cooking Class in Downtown Chicago: $64
  • Best in Chow: Chicago River North Food Tour: $64
  • Signature Food Tour at Chicago's Navy Pier: $64
  • Skip the Line: Tommy Gun's Garage Dinner and Show Ticket: $67
  • Small-Group Chicago Food Tour: Gold Coast and Old Town: $75
  • Best of Chicago Tour Including a Deep-Dish Pizza: $75
  • River North Walking Food Tour: $75
  • Chicago's Wicker Park Food Tour: $75
  • Private Indian-Mexican Fusion Cooking Class with a Modern Cook: $78

Food Tours and Cooking Classes in Milwaukee

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

  • Private Tour: Secret Food Tours Milwaukee: $90
  • Milwaukee Secret Food Tour w/ Private Tour Option: $193

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Chicago $34
    Milwaukee $21
Typical Entertainment prices in Chicago

Here are a few typical costs in Chicago for activities, ticket prices, and tours that come from previous visitors:


  • Sears Tower (family of 4)
    $102
  • Aquarium for 4
    $118
  • Water Taxi (family of 4)
    $22
  • IMAX Movie for Two
    $35
  • Shakespeare Play (2)
    $116
  • Art Institute (2)
    $36
  • U-Boat Tour (2)
    $8.00

Tours and Activities in Chicago

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

  • 2 Hours Chicago Sightseeing Tour - Luxury Private Stretch Limo / 8 Passengers: $250
  • 2-Hour Chicago City Lights and Skyline Segway Tour: $76
  • 2-Hour Chicago Fireworks Segway Tour: $76
  • 2-Hour Chicago Lakefront and Museum Campus Segway Tour: $73
  • 2-Hour Haunted Segway Tour of Chicago: $76
  • 2-Hour History of Chicago Architecture and Art Segway Tour: $75
  • 3 Hours Chicago Sightseeing Tour - Luxury Private SUV, ALL Inclusive: $392
  • 4 Hours Chicago Sightseeing Tour - Luxury Private SUV, ALL Inclusive: $220
  • 4 Hours Chicago Sightseeing Tour - Luxury Private Sedan: $215
  • 4 Hours Chicago Sightseeing Tour - Luxury Private Stretch Limousine/8 passengers: $728
  • A Most Magnificent Mile Shopping and Sightseeing Tour: $40
  • A Storied Neighborhood: Dance the dialectic with Bill Ayers on an audio tour: $5.00

Tours and Activities in Milwaukee

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

  • The Grand Walk: An audio tour through Milwaukee's historical and cultural heart: $5.00
  • Skip the Line: Museum Admission Ticket - Grohmann Museum: $5.00
  • Skip the Line: Chudnow Museum of Yesteryear Admission Ticket: $6.00
  • Skip the Line: North Point Lighthouse Admission Ticket: $8.00
  • Harley-Davidson Museum General Admission Ticket with Audio Guided Option: $22
  • Hop On Hop Off Sightseeing Bus Tour: $35
  • Ticket: $40
  • Cruisin' Karaoke Tour: $41
  • Discover Iconic Milwaukee Tour: $41
  • Fun Milwaukee Tours: $45
  • Fun Public Milwaukee Tours: $45
  • Christmas Past, Present and Future Light Tour: $70

For more ideas for your next trip, check out The Best Free Things to Do in Chicago, Chicago Bucket List: The Best Places to See, and The Best Museums in Chicago.


Alcohol
  • Alcohol Drinks for one day
    Chicago $20
    Milwaukee $26

Sample the Local Flavors in Chicago

Here are a few nightlife and alcohol tours and activities from local tour providers in Chicago:

  • Haunted Chicago Ghost and Pub Walking Tour: $25
  • Walking tour to Chicago dive bars: $41
  • Chicago Barrel Bus Craft Distillery Tour: $90
  • Chicago Craft Brewery Barrel Bus Tour: $90
  • Ultimate Girl's Night Out in Sparkling Wine, Photo Shoot, Burlesque: $900

Sample the Local Flavors in Milwaukee

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

  • Milwaukee Bar Hunt: Milwaukee Bar Crawl: $12
  • Operation Mindfall Brewery District in Downtown Milwaukee: $35
  • Operation Mindfall Bar Crawl on Brady Street: $35


When we compare the travel costs of actual travelers between Chicago and Milwaukee, we can see that Chicago is more expensive. And not only is Milwaukee much less expensive, but it is actually a significantly cheaper destination. So, traveling to Milwaukee would let you spend less money overall. Or, you could decide to spend more money in Milwaukee and be able to afford a more luxurious travel style by staying in nicer hotels, eating at more expensive restaurants, taking tours, and experiencing more activities. The same level of travel in Chicago would naturally cost you much more money, so you would probably want to keep your budget a little tighter in Chicago than you might in Milwaukee.


When is the best time to visit Chicago 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 Chicago or Milwaukee in the Summer?

The summer brings many poeple to Chicago as well as Milwaukee. Many travelers come to Chicago for the beaches, the city activities, the music scene, and the family-friendly experiences.

In July, Chicago is generally around the same temperature as Milwaukee. Temperatures in Chicago average around 77°F (25°C), and Milwaukee stays 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 Chicago this time of the year. In the summer, Chicago often gets around the same amount of sunshine as Milwaukee. Chicago gets 326 hours of sunny skies this time of year, while Milwaukee receives 321 hours of full sun.

Chicago receives a lot of rain in the summer. Chicago usually gets more rain in July than Milwaukee. Chicago gets 3.9 inches (100 mm) of rain, while Milwaukee receives 3.4 inches (87 mm) of rain this time of the year.


  • Summer Average Temperatures July
    Chicago 77°F (25°C) 
    Milwaukee 74°F (23°C)

Should I visit Chicago or Milwaukee in the Autumn?

Both Milwaukee and Chicago are popular destinations to visit in the autumn with plenty of activities. Many visitors come to Chicago in the autumn for the city's sights and attractions, the shopping scene, the music scene, and the natural beauty of the area.

Chicago is a little warmer than Milwaukee in the autumn. The temperature in Chicago is usually 56°F (14°C) in October, and Milwaukee stays around 53°F (12°C).

Chicago usually receives more sunshine than Milwaukee during autumn. At this time of the year, Chicago gets 195 hours of sunny skies, while Milwaukee receives 174 hours of full sun.

In October, Chicago usually receives more rain than Milwaukee. At this time of the year, Chicago gets 2.2 inches (56 mm) of rain, while Milwaukee receives 2 inches (50 mm) of rain.


  • Autumn Average Temperatures October
    Chicago 56°F (14°C) 
    Milwaukee 53°F (12°C)

Should I visit Chicago or Milwaukee in the Winter?

Both Milwaukee and Chicago during the winter are popular places to visit. Most visitors come to Chicago for the museums, the Christmas ambience, the shopping scene, the theater shows, and the cuisine during these months.

The weather in Milwaukee can be very cold. Chicago can be very cold during winter. In the winter, Chicago is a little warmer than Milwaukee. Typically, the winter temperatures in Chicago in January are around 25°F (-4°C), and Milwaukee is about 21°F (-6°C).

In the winter, Chicago often gets around the same amount of sunshine as Milwaukee. Chicago gets 134 hours of sunny skies this time of year, while Milwaukee receives 138 hours of full sun.

Chicago usually gets more rain in January than Milwaukee. Chicago gets 1.9 inches (47 mm) of rain, while Milwaukee receives 1.6 inches (41 mm) of rain this time of the year.


  • Winter Average Temperatures January
    Chicago 25°F (-4°C) 
    Milwaukee 21°F (-6°C)

Should I visit Chicago or Milwaukee in the Spring?

The spring attracts plenty of travelers to both Chicago and Milwaukee. The spring months attract visitors to Chicago because of the beaches, the activities around the city, and the natural beauty.

In April, Chicago is generally a little warmer than Milwaukee. Temperatures in Chicago average around 52°F (11°C), and Milwaukee stays around 47°F (8°C).

People are often attracted to the plentiful sunshine in Milwaukee this time of the year. In Chicago, it's very sunny this time of the year. Chicago usually receives around the same amount of sunshine as Milwaukee during spring. At this time of the year, Chicago gets 218 hours of sunny skies, while Milwaukee receives 211 hours of full sun.

Chicago gets a good bit of rain this time of year. In April, Chicago usually receives more rain than Milwaukee. At this time of the year, Chicago gets 4.3 inches (108 mm) of rain, while Milwaukee receives 2.8 inches (70 mm) of rain.


  • Spring Average Temperatures April
    Chicago 52°F (11°C) 
    Milwaukee 47°F (8°C)

Typical Weather for Milwaukee and Chicago

Chicago Milwaukee
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 25°F (-4°C) 1.9 inches (47 mm) 21°F (-6°C) 1.6 inches (41 mm)
Feb 29°F (-2°C) 1.4 inches (35 mm) 26°F (-4°C) 1.1 inches (29 mm)
Mar 41°F (5°C) 3.7 inches (93 mm) 36°F (2°C) 2.2 inches (57 mm)
Apr 52°F (11°C) 4.3 inches (108 mm) 47°F (8°C) 2.8 inches (70 mm)
May 63°F (17°C) 3 inches (75 mm) 58°F (14°C) 2.9 inches (73 mm)
Jun 73°F (23°C) 3.9 inches (100 mm) 68°F (20°C) 3.6 inches (91 mm)
Jul 77°F (25°C) 3.9 inches (100 mm) 74°F (23°C) 3.4 inches (87 mm)
Aug 76°F (24°C) 3.5 inches (90 mm) 72°F (22°C) 2.7 inches (68 mm)
Sep 68°F (20°C) 3.8 inches (96 mm) 65°F (18°C) 3 inches (77 mm)
Oct 56°F (14°C) 2.2 inches (56 mm) 53°F (12°C) 2 inches (50 mm)
Nov 44°F (7°C) 2.2 inches (56 mm) 41°F (5°C) 2 inches (51 mm)
Dec 31°F (-1°C) 2.8 inches (71 mm) 27°F (-3°C) 1.7 inches (44 mm)


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Chicago vs. Milwaukee Travel Comparison

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