Chicago vs. Milwaukee, Which City Should You Visit?

When it comes to choosing between visiting Chicago or Milwaukee, people often find themselves weighing various factors to make the best decision. These two sister cities both sit on the coast of the beautiful Lake Michigan only 97 miles apart, and because of this, they both have a lot in common due to their close proximity.

However, both cities also have their own brands of unique charm, rich histories, and urban atmospheres, making them great destinations no matter what your choice ends up being. In this article, we compare the costs, transportation, nightlife, activities, and food scenes of Chicago and Milwaukee to help you decide which city is best for you.

Chicago is well known for its towering skyline and busy city life, which comes with a higher cost of living compared to Milwaukee. Accommodations, dining out, and attractions can be pricier, making it a bit more challenging for budget travelers to navigate. However, the city has thousands of retail and restaurant options so there is a large range of price points to choose from, allowing for some budget flexibility depending on your spending plan.

Milwaukee, on the other hand, is generally more affordable. Whether it’s finding a place to stay, grabbing a drink, or visiting a museum, your dollar tends to stretch a little further here. This affordability may make Milwaukee an attractive option for those who want to explore a city without breaking the bank.

Chicago has a great public transportation network, at least for a city in the United States. The city’s extensive L train and bus system make it easy to navigate without a car. Additionally, Chicago is very bike-friendly, with 18.5 miles of barrier-protected bike lanes and the Divvy bike-share system available for use throughout the city. The city’s grid layout is straightforward, making it accessible for visitors to find their way around.

Milwaukee has a reliable bus system and a new streetcar system, The Hop, which opened in 2018 and is great for exploring the downtown area. However, Milwaukee is much less dense than Chicago, meaning stores, restaurants, and attractions may be farther apart. In many areas of the city, it may be more convenient to have a car to get around.

Chicago’s nightlife is energetic and varied, offering everything from jazz clubs and dive bars to high-end nightclubs and theaters. Neighborhoods like River North, Wicker Park, and Logan Square are all hotspots for those looking to experience the city’s well-known bar and club scene.

Milwaukee may be smaller, but its nightlife shouldn’t be underestimated. The city has a strong brewing heritage, which is reflected in its numerous beer gardens and brewery tours.

Chicago is a global city and is therefore home to world-class museums like the Art Institute of Chicago, the Field Museum, and the Museum of Science and Industry. The architectural river cruise is a must-do and features a tour guide narrating the history of the city’s architecture as you cruise along the Chicago River. The city also has 26 miles of lakefront access along Lake Michigan for residents and visitors to enjoy. Visitors making their way to Chicago should have a general plan for the things they most want to see and experience because it is next to impossible to accomplish everything the city has to offer in just one day.

Milwaukee also offers a good cultural experience but on a more manageable scale. The Milwaukee Art Museum, the Milwaukee Children’s Museum, and the Harley-Davidson Museum are just a few of the highlights that the city offers. Milwaukee also makes use of its proximity to Lake Michigan with 10.2 miles of Lakefront access of its own.