As amazing as Chicago is, with its food, amazing sites to visit and all that, it’s always nice for a little weekend getaway.
So, are you looking for a weekend escape away from the busy streets of Chicago? Are you looking for a small hidden paradise, where you can easily stroll down narrow cobblestone streets?
Or are you wondering what are other great cities near the Windy City that you could visit and explore for just a few days?
Keep reading for a little inspiration whether you are in the mood for a couple’s weekend trip, girls weekend trip or even a solo r&r trip as a personal treat. Below are our top 10 best weekend trips from Chicago.
10 Perfect Weekend Getaways From Chicago
We have already talked about the cool and amazing state parks near Chicago for those up for a little more adventure, in this post it’s all about those cool city breaks that you can easily do with a moments notice.
Those last-minute weekend getaways from Chicago that you can easily plan on a Thursday or Friday and be out on the road Saturday morning or even Friday night straight after work.
Many of these places are a couple of hours from Chicago so you can chill and for the weekend and come back relaxed to start a new week.
Amazing lakes views, beautiful parks, shopping, delicious food are what the weekends are all about. Another place that is is also stunning but wasn’t included on the list as I have covered it on the blog before is St Joesph, Michigan.
Less than 2 hours drive from Chicago is another little gem worth considering, particularly for those looking for weekend train trips from Chicago. Below are some fun and easy to arrange weekend getaways near Chicago.
1. Lake Geneva, Wisconsin
Located just an hour and a half away from Chicago, Lake Geneva is a real weekend paradise, especially during the hot summer months.
Known as one of the best lake towns in America, the resort offers everything from luxurious cruises to 30-mile hiking loops running along the lake.
With a huge number of colorful restaurants and bars, visitors can also enjoy world-class fine-dining experiences.
Besides relaxing and sunbathing by the beach, make sure to take a stroll through the downtown area and admire the old-style Victorian houses. Find the perfect stay around Lake Geneva here.
2. Galena, Illinois
If you are looking for a small picturesque town, you should make your way to Galena, Illinois. Getting lost in between the narrow cobblestone streets lined with beautiful historic mansions and admiring the views of green hills in the distance is a real treat after an entire week spent in between the busy streets of Chicago.
Regardless, if you just want to relax and sip on some delicious wine or you are looking for some outdoor activities, the quaint town of Galena has it all!
During the summer months, outdoor enthusiasts can choose between the meandering trails along the Mississippi River, while during the winter they can head to the Chestnut Mountains and the ski slopes nearby. Find the perfect stay in Galena here.
3. Saugatuck, Michigan
Known as one of the best summer weekend trips from Chicago, Saugatuck will greet you with its pristine beaches along Lake Michigan.
After spending an entire morning enjoying the well-known Oval Beach, head to the downtown area to experience the art and creative vibe of the town.
From the various art galleries to the small workshops, you cannot miss immersing yourself into the artistic and inspiring atmosphere.
Later in the afternoon, admire the stunning warm colors of the sunset before heading to the quaint downtown area to enjoy a delicious dinner. Find the perfect stay in Saugatuck here.
4. Elkhart Lake, Wisconsin
Approximately 140 miles away from Chicago, visitors can find a real hidden gem surrounded by crystal clear waters and peaceful and quiet nature.
Elkhart Lake, Wisconsin is just a small village in Sheboygan County, however, its laid-back and relaxing atmosphere is the perfect spot for a weekend getaway.
While the lake is perfect for water activities, such as fishing, boating and swimming, the popular Road America racetrack welcomes any racing fans.
Outdoor enthusiasts can also choose between numerous hiking, biking and running trails winding through the nearby Kettle Moraine State Forest. Find the perfect stay in Elkhart Lake here.
5. Indianapolis, Indiana
Art galleries, vibrant nightlife, green urban parks and much more welcomes anyone who is planning a weekend trip to Indianapolis, Indiana.
Those traveling with kids should pay a visit to the Children’s Museum of Indianapolis and the Zoo with its beautiful botanical garden.
Those that would like to spend a fun weekend, on the other hand, can head to the rooftop garden at the Fountain Square Theater Building, where they can sip on delicious cocktails.
Depending on what time of the year you are visiting, check the Hi-Fi Indy as they regularly host various music concerts. Find the perfect stay in Indianapolis here.
6. Milwaukee, Wisconsin
For anyone who loves beer tastings, the city of Milwaukee, Wisconsin is the best weekend trip from Chicago! Visitors can choose between the various craft breweries in the area and immerse themselves in the beer heritage of the city.
Art lovers, should make sure to stop by the Milwaukee Art Museum that is home to more than 25,000 of art pieces and displays.
If you are planning a family trip visit the 200-acres zoo or the butterfly garden at the Milwaukee Public Museum. Find the perfect stay in Milwaukee here.
7. Holland, Michigan
If you want to feel like you have traveled to another country, while still being in the United States of America and spending less than 3 hours to travel, you should visit Holland, Michigan!
Massively influenced by the Dutch heritage and culture, the small town is extremely picturesque and will certainly surprise you with its unique charm and atmosphere.
The Windmill Island Gardens and the Nelis’ Dutch Village are among the most popular sights across the city. A good idea is to plan a weekend trip from Chicago to Holland during the spring, so you can witness the six million tulips that are being planted yearly for the tulip time festival! Find the perfect stay in Holland here.
8. St. Louis, Missouri
You might wonder why would you change one big city for another! Well, St Louis, Missouri is like no other American city.
Despite its tall modern skyscrapers, the town has managed to preserve its charm and more peaceful atmosphere, thanks to the large green spaces along the Mississippi River.
Start the day by visiting what is known as America’s smallest national park with its symbolic 630-feet gateway arch. In the afternoon make sure to try some of the locally crafted beer that the city is known for.
If you are a baseball fan, you should certainly check the calendar if the Cardinals have some upcoming games! Find the perfect stay in St Louis here.
Get out to this beautifil city is super easy. You can take the train from Chicago to St Louis.
9. Detroit, Michigan
One of the best weekend trips from Chicago, especially during the summer months is the largest city in the state of Michigan – Detroit!
During the last few years, the city has become a synonym for a world-class dining experiences, so be prepared to treat your taste buds with at least one special dinner.
Known as the “Motor City”, due to its connections with the automobile industry, Detroit offers some extremely interesting sights, such as the Henry Ford Museum and the Detroit Institute of Art. Find the perfect stay in Detroit here.
10. Woodstock, Illinois
Just 60 miles away from the Windy City, Woodstock is one of the best weekend trips from Chicago. The small town is the perfect family-friendly retreat after a long busy week.
With its historic downtown district, Woodstock is a fantastic spot to take a step back in time and enjoy a laid-back afternoon while admiring the beautiful architecture.
As the town is located close to a number of natural parks and conservation areas, such as Pleasant Valley and Boone Creek, it is also hikers favorite location for some outdoor adventures and activities! Find the perfect stay in Woodstock here.
“47 miles from Chicago, Woodstock, Illinois is on the edge of the Chicago metropolitan area. We’re close to the city with a small town, rural personality all our own. Rich with Victorian architecture, a town square that seems frozen in time, and a world-renowned Opera House, Woodstock also has an independent streak brimming with creativity. We have the state’s largest concentration of apple orchards and berry farms. Our weekly Farmers’ Market is ranked one of Illinois’ best. And music, whether rock, folk, jazz, country or classical, fills the air indoors and out most every night.“
Essentials For The Perfect Weekend Getaway
- If you don’t already have you own car, you can easily get a rental car in Chicago.
- Have the perfect Weekender Bag at the ready!
- Book a tour or weekend experiences whether its food, music, photography or even cooking.
- Book an Airbnb or a hotel and you are good to go.
Did you manage to get some inspiration? Are you already planning your next weekend getaway? Which one of the above listed 10 best weekend trips near Chicago would you like to take first?
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