Getting from Milwaukee to Chicago

Transportation Options from Milwaukee to Chicago

Chicago and Milwaukee are just two hours away from one another by car, and it’s easy and cheap to travel between them. Inexpensive flight, bus, and train routes connect the two cities with frequent service.

Milwaukee to Chicago

  • Driving distance – 94 miles/150 kilometers


Delta, United, Southwest, American, Continental, and several other airlines offer frequent service from Milwaukee to Chicago. As always, prices go up around the holidays and peak travel times, but with advance purchase, you can usually get cheap tickets to Chicago for under $150 per person, round trip.

Journey time: Around 30 minutes
Typical price: $80 to $150 round-trip per person


Amtrak connects Chicago to Milwaukee several times a day. The trip is quick and easy, the trains are comfortable and they usually run on time.  Tickets range from $60 to $120 per person, round-trip.

Journey time: About 2 hours.


Megabus operates multiple routes between Chicago and Milwaukee. The buses are double-deckers and offer free Wi-Fi on board. With advance purchase, you can often get tickets for less than $10 per person round trip.

Journey time: 2 hours.


The drive between Chicago and Milwaukee can take 90 minutes to two hours, depending on traffic. Weekday traffic from 7am to 9am and 4pm to 7pm can be especially heavy.

Journey time: About 2 hours.

Driving from Milwaukee to Chicago: Pros and Cons

Driving from Milwaukee to Chicago is a popular option for transportation, and there are several pros and cons to consider before deciding whether to take this route. One of the main advantages of driving is that it allows you to stop and explore different areas, which can be a great way to break up a long journey. Also, driving can be more convenient if you have a lot of luggage or travel with a group.

However, there are also some downsides to driving. One of the biggest issues is traffic, which can be heavy, especially during peak times. This can significantly increase the time it takes from Milwaukee to Chicago. Another issue is parking – Chicago is a busy city, and finding affordable parking can be challenging. Also, driving can be stressful, especially if you are unfamiliar with the area. If you are uncomfortable driving in heavy traffic or unfamiliar areas, it may be best to consider other transportation options.

Public transportation: train and bus options

Public transportation is a great option for those who don’t want to drive or deal with the hassle of traffic. Luckily, several train and bus options are available for those traveling from Milwaukee to Chicago.
One popular train option is Amtrak’s Hiawatha Service, which runs between Milwaukee and Chicago several times daily. This service offers comfortable seating, Wi-Fi, and power outlets, making it a great option for those who need to work or stay connected during their journey.

Another popular train option is the Metra, which operates commuter trains between Chicago and its suburbs. The Milwaukee District North line runs from Chicago Union Station to Fox Lake, with several stops in between.

If you prefer taking a bus, several options are also available. Greyhound and Megabus operate daily services between Milwaukee and Chicago, with fares starting at just a few dollars. These buses offer comfortable seating, air conditioning, and free Wi-Fi, making them a great option for budget-conscious travelers.

Flying between Milwaukee and Chicago: Is it worth it?

Many consider flying between Milwaukee and Chicago a transportation option due to its convenience and speed. However, it’s important to consider if it’s worth it for you since there are some drawbacks to flying between the two cities.

Firstly, if you consider the time it takes to get to the airport, check-in, go through security and wait for your flight, flying may not be any faster than driving or taking the train. The travel time may be longer due to the additional steps involved in air travel.

Secondly, the cost of flights can be higher than other transportation options, especially if you book last minute or during peak travel times. Additionally, there may be additional fees for checked baggage, seat selection, and other add-ons that can quickly add up.

However, there are some advantages to flying. Flying can be a good option if you’re short on time or need to get to your destination quickly. Additionally, flying may be the only practical option if you’re traveling internationally or to a far-off destination.

Ride-sharing options: Uber and Lyft

Ride-sharing options like Uber and Lyft have become increasingly popular as convenient and affordable transportation options in recent years. Both Uber and Lyft operate in Milwaukee and Chicago, making it easy to get a ride from one city to the other.

You only need a smartphone and the Uber or Lyft app to use these services. Simply enter your pickup location and destination, and the app will match you with a nearby driver. The ride cost will depend on factors such as the distance traveled, the time of day, and the level of ride demand.

One benefit of ride-sharing is that it’s often faster than public transportation, as you can be picked up and dropped off exactly where you need to go. Additionally, ride-sharing services are available 24/7, so you can travel anytime or at night.

However, ride-sharing isn’t always the most cost-effective option, especially for longer trips. You may also experience surge pricing during times of high demand, which can significantly increase the cost of your ride. It’s always a good idea to compare prices between ride-sharing and other transportation options to determine what works best for your needs and budget.

Private car services and limousines

When it comes to private car services and limousines, plenty of options are available for transportation from Milwaukee to Chicago. These services offer a luxurious and comfortable ride, making them a great option for special occasions or business travel.

One of the benefits of using a private car service or limousine is the convenience. You can schedule your pick-up and drop-off times around your schedule, eliminating the need to wait for public transportation or deal with the hassle of driving and finding parking. Private car services and limousines also offer a more personalized experience, with drivers who are knowledgeable about the area and can offer recommendations for restaurants, attractions, and other points of interest along the way.

Another benefit of using a private car service or limousine is comfort. These services typically offer spacious and luxurious vehicles with amenities like leather seats, climate control, and entertainment systems. This can make your ride more enjoyable, whether traveling for business or pleasure.

When choosing a private car service or limousine, it is important to research and choose a reputable company with a track record of providing reliable and safe transportation. Look for companies with a fleet of well-maintained vehicles and licensed, insured, and experienced drivers. You should also check customer reviews and ratings to get a sense of the level of service you can expect. You can enjoy a stress-free and comfortable ride from Milwaukee to Chicago with the right private car service or limousine.

Cost comparison and tips for getting the best deals

When it comes to traveling from Milwaukee to Chicago, various transportation options are available, each with its own costs and benefits. It’s important to compare the options and get the best deals possible to save money while traveling.

If you’re traveling by train, Amtrak is the most popular option, with fares starting at around $25 one-way. However, booking your tickets in advance is important to get the best deals and avoid inflated prices closer to the travel date.

If you prefer to drive, renting a car can be cost-effective, especially if traveling with a group. Car rental companies often offer discounts and promotions, so compare prices and book in advance for the best deals.

Another option is to take a bus, with companies like Greyhound and Megabus offering affordable fares starting at around $10 one-way. Like trains, booking your tickets in advance is important to get the best deals.

When comparing costs, it’s important to consider additional expenses like parking or tolls if you’re driving or baggage fees if traveling by bus or train. Additionally, watch for special promotions or discounts, such as student or military discounts.

How to plan your trip and book your transportation

Planning your trip from Milwaukee to Chicago can be a breeze if you know the available transportation options and how to book them. First, decide which mode of transportation you prefer. If you want to fly, check out airlines that offer flights from Milwaukee’s General Mitchell International Airport to Chicago’s O’Hare International Airport or Midway International Airport.

Be sure to compare prices and schedules to find the best deal and fit for your schedule. If you prefer to drive, consider renting a car from Milwaukee or taking your own car and parking it in one of Chicago’s many parking lots or garages. However, be aware that parking can be expensive in the city and traffic can be heavy, especially during rush hour.

Another option is taking the train. Amtrak offers several daily routes from Milwaukee’s Intermodal Station to Chicago’s Union Station. This is a popular option for commuters and travelers who want to avoid driving and navigating through traffic. You can also consider taking a bus, with companies such as Greyhound and Megabus offering affordable and convenient options from Milwaukee to Chicago.


We hope you found our ultimate guide to transportation options from Milwaukee to Chicago helpful. Whether you’re a local or a visitor to the area, navigating all the different transportation options available can be overwhelming. We hope that we’ve provided you with all the information you need to decide which mode of transportation is best for you. Safe travels, and let us know in the comments which option you choose!

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