10 Best Weekend Trips From Chicago, Illinois

weekend getaways from chicago
Swadeep Singh
Swadeep Singh

Chicago is an incredible metropolis, and it is hard to imagine that someone could even get bored here. From the downtown fun to outdoor adventures, this city is truly a complete package. However, we also cannot deny the fact that eventually, you will cover most of its goodness and then desire for more. This reality will apply to the residents as well as the outsiders, who have lived here for a longer time. Gladly, the geographic positioning of Chicago makes it possible that you will ever get exhausted from a tour plan. There are so many amazing destinations near the city and around the lake, which could serve the purpose of your short-vacation desire. In the same vein, we are going to share a list that will help you plan the best weekend trips from Chicago, Illinois. Stay with us on this page to get some valuable information.

1. Madison, Wisconsin

Madison, Wisconsin
Source: Pixabay

Madison is located approximately 150 miles (236 kilometers/ 2-hour drive) to the northwest of Chicago. Madison is the capital city of the state of Wisconsin and it possesses tonnes of tourism opportunities. Nicknamed ‘the city of four lakes’, it literally sits between an isthmus between the two major ones which are Lake Mendota and Lake Monona. The state parks, in addition to these lakes, make this city a wonderful destination for nature lovers. Then, the downtown region has several museums, for instance; The Children Museum, Veteran Museum, Physics Museum, and Mustard Museum. Besides, Madison has one of the oldest synagogues in the world.

2. Saugatuck

Saugatuck MI from Mount Baldhead
Source: Photo by user Robert Moore used under PUBLIC DOMAIN

The name of this city was taken from the Native American term, Saw-gu-tuck, which literally means the mouth of a river. Situated on the east coast of Lake Michigan at 140 miles (225 miles/ 2-hour drive) from Chicago, Saugatuck has served as a lumber town and a port for very long, and thus, it was given this unique name due to its proximity to the Kalamazoo River. Today, the city has been developed into a famous tourist destination of this state. The art and craft movement of the previous century provided this city with over a dozen galleries. However, if you’re not very interested in history, you will definitely like the Oval Beach, Dune Rides, and hiking trails.

3. Door County

Door County, Wisconsin
Source: Photo by user Deb Nystrom used under CC BY 2.0

Door County is one of the top tourist destinations in the state of Wisconsin, and it’s at least 244 miles (390 kilometers) from Chicago. It was established on a peninsula between the two massive water bodies, Lake Michigan and Green Bay. This region is world-renowned for pristine splendors that can be appreciated throughout the years. However, representing each of them will be totally unattainable inside of this one paragraph, but we are also confident that you will get an idea. Door County presents you over 300 miles (480 kilometers) of coastline, 19 county parks, 5 state parks, 11 historic lighthouses, over 10 communities, and more wonders.

4. Ottawa

Grand Haven MI - outer light
Source: Photo by user Sandysphotos2009 used under CC BY 2.0

Ottawa County is based approximately 166 miles (267 kilometers/2.5-hour drive) away from Chicago, and it is positioned on the east coast of Lake Michigan. Long ago, this region was the home of the population of Ottawa, Chippewa, and Potawatomi Indians, and touring this side should help you to learn the aboriginal heritage of these tribes. Besides, there are at least 15 communities and several historic sites scattered around in this county. And for nature lovers, Ottawa features lake recreation and hiking opportunities in many state and local parks, for instance - Hoffmaster, and Grand Haven State Park.

5. Rockford

Rockford, IL Jefferson Street Bridge
Source: Photo by Wikimedia Commons user Kranar Drogin used under CC BY 2.5

Rockford is the third-largest city in the state of Illinois, and it comes at about 88 miles (141 kilometers/1.5-hour drive) from Chicago while en-route to Madison. But it’s not just the nearness of this city to Chicago that makes it an appropriate part of our list; the city of Rockford is itself an attraction. It’s the city of gardens and rivers, and there are a number of places worth visiting. To name a few, you might want to consider Anderson Japanese Gardens, Klehm Arboretum, Burpee Museum, and Midway Village Living Museum. The Art Deco and Prairie School architecture of the historic commercial area is also a sight to see.

6. Grand Rapids

Downtown Grand Rapids from River House
Source: Photo by user Rachel Kramer used under CC BY 2.0

Grand Rapids is 179 miles (288 kilometers/2.5-hour drive) distance to the city of Chicago, and it is located right next to the Ottawa County. Nicknamed the ‘River City’ for the very obvious reason, Grand Rapids is also called the ‘Furniture City’ due to its furniture-manufacturing heritage. It’s the second-largest city in the state of Michigan, and you truly have endless tourism opportunities in its metropolitan. Starting with the museums in its downtown, the Grand Rapids Public Museum, Grand Rapids Art Museum, and Grand Rapids Children Museum are the most notable. Besides, you must also not skip Frederik Meijer botanical garden and outdoor sculpture park, and John Ball Zoological Garden.

7. Geneva, Illinois

Geneva IL State Street Streetscape
Source: Photo by user Karla Kaulfuss used under CC BY 2.0

Being at 42 miles (67 kilometers/ 45-minute drive) west of Chicago, Geneva is the nearest of all the locations which we have listed on this index. This small scenic town is settled on the banks of Fox River and it has a wonderful historical past from the 19th century. While touring this place, we recommend you set your priority to the Geneva History Museum, Fabyan Forest Preserve, and Fox River Trail. Then, BAPS Shri Swaminarayan Mandir in Bartlet Village can also be visited to check out its glorious architecture. You can also take tours of breweries, distilleries, and chocolate factories.

8. Mackinac Island

Mackinac Island Overlook
Source: Photo by user Lynnanderson used under CC BY-SA 3.0

Located at 413 miles (664 kilometers/ 8-hour drive) from Chicago, Mackinac Island is the farthest of all the locations which we have listed. It can be reached via Mackinaw City, after which, you would have to take a ferry ride. You’ll find this location very unique, as an ordinance has restricted the use of any kind of automobile on this island (except for the emergency service), for over a century. The island can only be explored on foot, bicycles, or on a horse. Mackinac Island State Park and Round Island Lighthouse are the two more famous attractions here, and Mackinac Island fudge is the best souvenir of this place.

9. Milwaukee

Downtown Milwaukee
Source: Photo by user

Milwaukee is located on the western shores of Lake Michigan at 92 miles (148 kilometers/ 1.5-hour drive) north of Chicago. Milwaukee is the largest city in the state of Wisconsin, and it’s often referred to as the city of little neighborhoods. And since the districts are dissimilar in their styles, they contribute alternative reasons to visit this big city. For instance, Walker’s Point is artistic, Clarke Square has cultural communities, and Bay View has retro vibes. But if you still require some more places to visit, head to Milwaukee Art Museum, Harley Davidson Museum, and tour the breweries in Milwaukee.

10. Traverse City

Traverse City Skyline
Source: Photo by user Phoenix-Five used under CC BY-SA 4.0

On the final spot of our list, we would like to show you a really good tourist destination in Northern Michigan: Traverse City. Located at 318 miles (511 kilometers/4.5-hour drive) distance to Chicago, Traverse City is worth visiting in every month. Nicknamed as ‘the cherry capital of the world’, this region grows up to 160,000 tonnes of cherries annually and has over 50 wineries. Traverse City also features several beautiful beaches like West End Beach, and a cycling trail network named TART trail system. And it’s world-renowned for its film and cherry festival.

Memorable weekend getaways await

Downtown Milwaukee from Pier Wisconsin
Source: Photo by Wikimedia Commons user Yk Yk Yk used under CC BY-SA 3.0

As you must have seen in this article, our index covers different tourist destinations. We have presented you sightseeing opportunities in big cities like Milwaukee, as well as in remote places like Mackinac Island. While there are some places appropriate for just summer, you should have also read about Traverse City, which is worth visiting throughout the year. Let’s hope that our article of the best weekend trips from Chicago, Illinois, will help you.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Nicknamed Bobby, Swadeep Singh is a businessman since 2013, but he has forever been a writer. Traveling places never makes him exhausted, that is why he never say no to any travel plan. If he’s not...Read more

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