Weekend Getaway From Chicago

Your Complete, Two-Day Itinerary for a Michigan Weekend Getaway From Chicago


Kalamazoo, Michigan is just over two hours from Chicago, making it the perfect weekend getaway. Escape the hustle and bustle of the city for a smaller-town experience with big-town vibes. From local eats and craft brews to hiking and biking trails for every skill level, you can rest assured that you will discover new adventures and hidden gems all weekend long. Be sure to check out @busybeatravels on Instagram for a more in-depth look at what a weekend getaway from Chicago can really look like! 


Whether you’re looking for an outdoor adventure, exciting attractions, or relaxation and retail therapy, Kalamazoo has something for everyone. Bring your family, a special someone, or even just yourself, and see what a Michigan weekend getaway from Chicago looks like in Kalamazoo.


Your Michigan Weekend Getaway Itinerary at a glance: 

Day 1: Check out Factory Coffee to fuel up before your first day in Kalamazoo! Then, get outside and explore the Kalamazoo Nature Center where you can hike and enjoy wildlife! And finally, grab a bite to eat at Cosmo's Cucina, an affordable, gourmet dining experience with creative dishes. 

Day 2: Relax & Shop Local - Try our local favorite breakfast spot, Nina’s Cafe, before shopping at the Downtown Kalamazoo Mall. After you’ve worked up an appetite, stop into Cookie’s Five Star Grill, for some delectable soul food. End your Michigan weekend getaway from Chicago at Twine Urban Winery or Dabney & Co. depending on what you’re in the mood for!



The perfect kickoff to your weekend getaway from Chicago is sipping some locally brewed specialty coffee and filling up on both savory and sweet treats at Factory Coffee. This family-owned roastery features ethically roasted coffee in two convenient locations, one of them being in the heart of downtown. Their limited-edition food items and coffee and tea options are sure to get your day–and weekend–off to a great start.


Factory Coffee


From there, head about five miles north to the Kalamazoo Nature Center and enjoy more than 14 miles of hiking trails winding through various landscapes. These trails range from easy to difficult, with all sorts of adventures along the way including wildlife, scenic views, and animal ambassadors that are being rehabilitated. The center also features rotating educational exhibits and activities, local arts, and featured programs for kids and adults. Admission is $7 for adults and $4 for kids ages 4+.


Exterior view of the nature center in fall


To conclude day one of your Michigan weekend getaway from Chicago, head 15 minutes down the road to Cosmo’s Cucina. This locally-owned business offers a contemporary oasis with affordable, gourmet cuisine. Serving up the community since 1992, this Kalamazoo hidden gem restaurant works with local farmers to source the best, freshest ingredients. Their menu features creative dishes from kimchi fried rice to oven-roasted duck to classic burgers! After your belly is full, head back to your hotel to catch some Z’s and rest up for an exciting day two. 



Since day one of your Michigan weekend getaway from Chicago focused on getting outside and exploring the Southwest Michigan scenery, day two is all about unwinding and showing support to some of Kalamazoo’s local and black-owned businesses. Start this relaxing day off with one of Kalamazoo’s classic breakfast favorites, Nina’s Cafe. This family-owned diner has been serving their generously sized pancakes since 1991. Their flavors are nearly limitless, from traditional buttermilk to blueberry or even pumpkin! They also offer all the savory favorites you could imagine. There’s no better place to fill up before shopping and exploring the day away on your weekend getaway from Chicago! 




Just five minutes up the road is the Kalamazoo Valley Museum, a free, interactive museum that is fun for everyone! The Kalamazoo Valley Museum was voted the top small museum in Michigan by readers of Michigan Living Magazine and it offers “adventures you can touch” while celebrating history, science and technology! It features a planetarium, a 2,300 year-old mummy, and an interactive history gallery. You definitely don’t want to miss out on experiencing the Kalamazoo Valley Museum on your weekend getaway from Chicago. 

After you’re done learning about Kalamazoo and the surrounding regions, make your way down to the first outdoor pedestrian mall in the US, the Downtown Kalamazoo Mall. Here, you’ll find more of Kalamazoo’s staple shops, eateries and activities.


Cherri's Chocol'art


Located in the heart of it all is a chocolate lover’s paradise, Cherri's Chocol'art. This unique store features a full coffee bar, ice cream bar, and handmade chocolate treats. It is also home to the Monster Shake, a milkshake with custom flavors and toppings! Stop in and taste their high-quality chocolate art! One of Kalamazoo’s newest sustainable shops, and Michigan’s first Zero Waste shop, Bee Joyful, is also located along this mall. Sustainability, being Earth-friendly and leaving things better than how you found them, are the heart and soul of Bee Joyful, where you can find self-care products, home goods, and cleaning supplies. The Downtown Kalamazoo Mall is filled with all sorts of local shops and hidden gems you won’t want to miss during your Michigan weekend getaway from Chicago.

The day isn’t over yet! After you’re sure to have worked up an appetite, head down the street to Cookie’s Creole ‘N’ Soul Five Star Grill for some of the best soul food you’ve ever tasted! This spot is always packed and serves up some of the most delicious seafood and creole-inspired dishes with their daily specials and entree items. Don’t worry about the potential long lines, we promise it’s more than worth it for your last meal on your Michigan weekend getaway from Chicago! 

Another local business worth visiting on your weekend getaway from Chicago is Twine Urban Winery. Their tasting room offers reservations to taste flights, wine by the glass, wine cocktails, or their famous wine slushie! They also offer cheese, chocolate and other light appetizers. Make sure to book your reservation to not miss out on this opportunity! 


Dabney & Co. drink service


Looking for a crafted cocktail instead? Check out one of Kalamazoo’s newest lounges, Dabney & Co. and try their signature Mint Julep, an homage to the first renowned Black bartender, John Dabney. Black-owned and operated, Dabney & Co. is an elegant, moody space where patrons will indulge in fresh, hand-crafted beverages and savor classic soul food with a unique spin, served á la carte.

Our friend Busy Bea Travels (@BusyBeaTravels) visited many of these recommended places on her recent Michigan weekend getaway from Chicago. Be sure to check out her videos for more information on things to do while you’re here! 


We can’t wait to host you on your next weekend getaway from Chicago! The hustle and bustle of city life sometimes calls for an escape– Kalamazoo is the perfect spot being just a short two hour drive away. Plan your trip and get exploring (or relaxing). After spending your day exactly how you need to, catch some rest at one of the places to stay in Kalamazoo or book one of our specialty hotel packages.

For more information to aid your trip planning, be sure to request a visitor’s guide and subscribe to our e-newsletter to get the latest and greatest Kalamazoo. And, don’t forget to check out our calendar of upcoming events to see what’s going on in the area during your visit!

Find unbelievable deals that come with everything you need to enjoy a trip to Kalamazoo, including overnight accommodations, free hotel parking and more.

Experience exciting new flavors at distilleries and cocktail bars throughout Kalamazoo, discover the popular Downtown Social District, or attend one of the many tastings, happy…

Downtown Kalamazoo boasts the nation’s first outdoor pedestrian mall, complete with unique restaurants, breweries, shops, DIY experiences, and live entertainment.