Chicago is the United States' third largest city with a population of nearly 3 million. The larger Cook County is the second-most-populous county (right behind Los Angeles County) with over 5 million people. Geographically, Chicago spans more than 25 miles from north to south and 15 miles east to west, boasting 200 neighborhoods and two airports. To say Chicago can feel a bit crowded at times is quite an understatement!
Only an hour and a half train ride away is a city that resembles more of a Chicago suburb but still offers much of the same quality entertainment, dining, diversity, and cool midwest weather. If you're looking for a weekend getaway from the hustle and bustle from Chicago, consider taking a ride on the red line to Union Station, and pay for a $25 ticket toward Milwaukee. Not only is the train a great way to get from downtown Chicago to downtown Milwaukee, it's generally an underestimated way to travel. As a matter of fact, the train between these two cities is so popular, several Chicago employees live in Milwaukee and use the train as their daily commute.
Not only is the train economically and environmentally friendly, the Metra has extra leg room, an electrical outlet at each seat, and a "quiet car" for passengers requiring a calm and peaceful travel. It makes a limited number of stops between Chicago and Milwaukee (one is the Milwaukee airport if you need a 3rd option for flying) and just earlier this year, they've taken extra steps to protect against COVID-19. You can easily plan your weekend getaway to leave on a Saturday morning and return that evening. If you need a longer escape, consider booking an Air BnB or finding a downtown hotel in Milwaukee for a single night.
As a rich mix of cultures, Milwaukee celebrates a different nationality each weekend throughout the summer. In addition to the big outdoor concert known as SummerFest (similar to Chicago's Lalapalooza), the other summer weekends feature groups from Milwaukee's rich history. Look up weekends celebrating the Polish, Germans, Native Americans, Mexicans, Scottish and Italians. At these festivals (all in Milwaukee's 3rd ward, just a few blocks from the train station), visitors can try foods from each culture, learn about traditions and customs, hear live music performed with native instruments (I can still hear the Scottish Festival bagpipes in my head!), and most importantly, celebrate a culture with the Milwaukee residents that reside there. Even just hearing a different language during casual conversation as I walk through the festival grounds is testament to the diversity and seems to enrich the celebration.
If heritage festivals aren't your thing, Milwuakee also features Pride, Film Fest, Beer Brews, has their own casino, baseball team, basketball team, outdoor hiking trails, river walks, and alot of the other familiar events Chicago celebrates each year. Known as the City of Festivals, it's easy to find something to do in Milwaukee on any given weekend.
After a fun afternoon, Milwaukee's nightlife offers plenty of options. It's easy to find restaurants near the festival grounds, bars for every demographic, and if you're staying overnight, consider spending the next morning visiting one of the museums or taking a quiet outdoor walk (or bike ride) along one of the nearby hiking trails (yes, you can arrange to take your bike on the train from Chicago to Milwaukee).
With minimal effort and less than $100, you can easily take a break from the crowded, noisy, city life Chicago offers, hop a train to downtown Milwaukee and enjoy a day or weekend in an undiscovered (or at least, underrated) gem of the midwest. By the time you return to your routine in the big city, you'll feel a bit more relaxed, a bit more calm, and a bit more settled. For me, taking this break left me feeling a bit more balanced and refreshed.
Even though the suggestion here is to visit Milwaukee during the summer months, its a fun city to visit all year round. Who knows, you might even find some new friends and connect with some strangers that soon become travel buddies (they can come visit you in Chicago!) If you're on a tight budget, can't afford to take time off work, but like so many of us, need an occasional break from our routine, consider a trip to Milwaukee Wisconsin one weekend. You just might be surprised.
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