7 Easy Chicagoland Weekend Getaways Within 200 Miles

If wanderlust is starting to take hold put away your passports because you won’t need airfare to travel to these places. You probably won’t even need a hotel, but we’ll leave that up to you. Pick any weekend and go on a mini-vacation with these seven easy Chicagoland weekend getaways.

1. Indiana Dunes National Lakeshore – Distance from Chicago: 47 miles

Indiana Dunes National Lakeshore is perfect for a day trip or a full outdoor weekend adventure. In addition to 15 miles of protected lakeshore beach, the park has 50 miles of hiking over 14 distinctive trails.

Taking in The Sunset

Where to stay: The Dunewood Campground features 54 drive-in sites and 12 walk-in sites. The campgrounds only cost $18 per night, but they are first come, first serve. If you can’t get a campsite (or camping isn’t your thing) there are several hotels within spitting distance of the park. Spring House Inn is fairly reasonably priced and features amenities including a pool and ease of access to hiking. The DunesWalk Inn is a bit on the higher end, but it’s a mansion from 1881 and is quaint AF. If you can stretch your pennies it comes highly recommended. If you have 10-20 friends the whole building is available for around $800 per night.

What to do: In addition to the ample hiking mentioned above other activities include kayaking, biking, fishing, birdwatching and more. Check out the Old Lighthouse Museum or head to Michigan City’s Washington Park Zoo. If you’re looking for a cozy nighttime experience away from the campground head down Route 49 to the classic 49er  Drive-in.

Where to eat:

If you aren’t eating at your campground you’ll need to drive into one of the nearby towns.

  • Breakfast: Northside Diner might not look like much on the outside, but the breakfast/brunch gets thumbs up.
  • Lunch: Ivy’s Bohemia House in Chesterton is adorable and has an eclectic menu. The spanakopita could compete with some of the best in Greek Town.
  • Dinner: Shoreline Brewery is the top choice for great food and beer. Try the Old World Pierogis or the Bourbon Pork.
  • Dessert: If you’re checking out the 49er Drive-in you might as well as add Chesterton’s Dog Days Ice Cream Parlour to the itinerary.

2. Rockford, Ill. – Distance from Chicago: 90 miles

Rockford is a simple and relaxing escape from Chicago. An easy drive west on 90, Rockford makes for a great day or weekend trip.


Where to stay: Rockford struggles a bit when it comes to hotels. You’ll probably end up at a Comfort Inn unless you can find a decent AirBnB.

What to do: Rockford has a cute downtown for exploring. Be sure to check out the public gardens, including the serene Andersonerson Japanese Gardens and Nicholas Conservatory and Gardens. Meander along the Rock River Recreation Path and view mansions leftover from when Rockford was an industrial titan.

Where to eat:

  • Brunch: We’re attracted to puns, so Eggsclusive made it to the top of our list. Thankfully, the food is worth it with the Butcher Benedict being a top choice. Fresco at the Gardens has the best brunch view in the city.
  • Dinner: Can’t go wrong with Social Urban Bar and Restaurant. Not only is the food astounding, but the cocktail program would fit well within Chicago city limits. Also worth checking out is Carlyle Brewing Company which pairs craft beer with pub-style food. Also, worth checking out is Prairie Street Brewhouse next to the marina.
  • Dessert: La Michocana is Instagram ice cream heaven. Bella Luna Bakery has a killer cheesecake. sugarjones is the place to go for cupcakes.

3. Milwaukee, Wis. – Distance from Chicago: 95 miles

Ah, Milwaukee, much like Chicago you suffer from dismissive coastal stereotypes that write you off as a second rate city. In reality, Milwaukee is a laid-back city with beautiful architecture (admire those cream-colored bricks that give Milwaukee the nickname Cream City) and set on a stunning lake. The culture is strong and proud but also inviting. Milwaukee is bikeable, has excellent museums and alternative theater, a growing cocktail culture, some okay sports teams, a thriving music scene, and is easy to navigate. Bonus, in comparison to Chicago it’s cheap thanks to a lower sales tax. You can go out and do many of the things you’d do on a typical night in Chi-town and still go home with cash in your wallet.


Where to stay: Sure Milwaukee has the usual chains, but for some reason, this city also has a lot of cool and unusual hotels. I mean, we could do an entire post focused solely on Milwaukee hotels. That said, one of the oldest, most interesting, and best priced is The Astor. It isn’t even a debate. This classic hotel is not only a quaint step back into Milwaukee history, but it’s ridiculously affordable. Rooms are often in the $90 range. However, if you’re feeling spendy (we’re talking an average of $350 per night in the summer and $250 range in the winter) consider the Iron Horse Hotel. In addition to putting you up in a fancy loft room, the Iron Horse offers affordable packages like the “museums and motorcycles” which gets you into the Milwaukee Art Museum and the Harley Museum. In the middle of the road of pricing, you’ll find the Brewhouse Inn and Suites. This Inn describes itself as “post-Victorian steampunk meets urban-contemporary elegance.” It’s a beautiful hotel and is sure to inspire romance.

What to do: Milwaukee is one of those weekend trips that deserve an entire post, so expect that shortly. If you love Chicago’s Field Museum you’ll want to prioritize the Milwaukee Public Museum. Although the MPM suffers from one of the most boring names for a museum it’s actually incredibly fascinating. You’ll stroll through the streets of Old Milwaukee, immerse yourself in the rainforest, and explore the African Serengeti. You’ll also want to visit the Milwaukee Art Museum and the Harley-Davidson Museum (even if you don’t like motorcycles). Milwaukee is also a bike friendly city, so rent a bike and grab a bike map. Much like Chicago, Milwaukee takes a great deal of pride in neighborhood festivals, so do some research and celebrate like a local.

Where to eat:

  • Brunch: If this is your first time brunching in Milwaukee it’s hard to not send you to Comet Cafe. Comet practically invented Milwaukee’s hipster brunch.  Mad Rooster Cafe is a rising star in Milwaukee’s brunch scene and you should probably just take our advice and order the Stuffed French Toast. Looking for something a little different for brunch? Try the Korean BBQ Breakfast Bowl at Simple Cafe. Engine COmpany 3 has one of the coolest brunch spaces in MKE and you’ll want to devour one of the restaurants many french toast options.
  • Lunch: Milwaukee is second-only to Chicago when it comes to pizza (NYC who?). We recommend the Hot Marmont pizza at Wy’East or the vegan Anne Curry at Classic Slice (yeah, we said vegan, but it is so damn good). Tandem is a fun blend of Detroit and Milwaukee. Grab an order of hushpuppies to go with the Detroit dog (they also have a Chicago dog, but ffs you’re on vacation).
  • Dinner: Ramen might not be the first thing to spring to mind when you think of Wisconsin, but Red Light Ramen will give most Chicago ramen places a good run for their money. Third Coast Provisions is killin’ it with seafood option. The menu has a decent selection of small plates with standouts like lobster potholes and oyster sliders. Sanford is a little bit on the higher end but definitely worth the cost. If you visit during the week consider taking advantage of the “exploration menu” or the “surprise menu.”
  • Dessert: “I’m going to visit Milwaukee and not eat custard,” said Noone Ever. You could spend an entire day doing it, but we recommend sticking with tradition and hit Kopp’s or Leon’s.
  • Drink: This is so difficult. Southern Wisconsin, thanks mostly to Milwaukee and Madison (as you’ll see in a moment), has been experiencing a cocktail boom for nearly a decade. It’s actually rather shocking Wisconsin doesn’t make this drinking corridor part of tourism marketing. Cheese is cool and all, but no one talks about the bomb-ass cocktail culture. On top of that, you have all of the fantastic breweries in and surrounding those two cities. Here’s a quick but hardly complete list of where you need to go to kill your liver.

4. Starved Rock State Park – Distance from Chicago: 100 miles

One of the most beautiful locations in Illinois. THis is the perfect day or weekend trip for getting away from the hustle and bustle of city life.


Where to stay: If you want to stay in Starved Rock there’s a campground. If you prefer a roof and bed check out Grizzly Jack’s Grand Bear Resort (they have water slides) or the Starved Rock Lodge. You can also try the Willows Hotel in nearby North Utica.

What to do: Be outside! Starved Rock has 18 canyons, 14 waterfalls, and 13 miles of hiking trails. You could do it all in one day or break it up over the weekend.

Where to eat:

  • Brunch: We’re a little lost when it comes to straight up breakfast in this area of Illinois. We can recommend Pink Chihuahua for lunch.
  • Dinner: Head to nearby Ottawa for The Lone Buffalo. Eat from a farm fresh seasonal menu and sample craft beer from Tangled Roots Brewing Company.

5. Madison, Wis. – Distance from Chicago: 147 miles

Madison is a city undergoing an identity crisis thanks to a growing tech industry fueled in part by health care IT giant Epic. There’s a solid population of millennials with cash to burn, but also with humble Midwestern values. Instead of spending that money on fancy clothes and flashy clothes, Madisonians are more likely to spend it on food and drink. As a result, Madison has become a foodie destination city. On top of that, although Madison is only 76 square miles, this small Midwestern city supports a healthy music and arts scene which attracts a surprising amount of touring acts. That reality often earns Madison (to the chagrin of local curmudgeons) the misplaced title of “Austin of the Upper Midwest.” Madison is Madison, dammit.

Madison Capitol

Where to stay: The Livingston Inn is the definition of “cozy.” This gothic revival bed and breakfast is on the edge of Lake Monona providing easy access to downtown and watersports on the lake. Over by Madison’s other lake, Mendota, you’ll find the equally charming Ruby Marie.  COnsider asking for Room 23 which comes with a hot tub, fireplace, and view of the lake. The Graduate is what you’d get if Wes Anderson gave up filmmaking and instead designed a hotel. The chic boutique hotel is located right on the edge of the UW campus, but don’t let that deter you. If you’re looking for something a little bit more traditional try Madison’s Concourse Hotel right next to the Wisconsin State Capitol Building or the colorful Hyatt Place.

What to do: Is it summer? Check the schedule at Breese Stevens Field and see if you can catch an outside concert. Check the Marquette Neighborhood festival calendar and check out one of the city’s many summer block parties. Or maybe you’re lucky enough to be in town for one of the many free concerts on King Street or the Wisconsin Film Festival.

As the headquarters of Trek, Madison is a top-notch bike friendly city, so take advantage of the numerous bike trails. If you like the water, rent a canoe or paddle boat and hit the lakes. Of course, you’ll want to check out the state capitol for both the architecture and the Saturday Farmer’s Market (there’s a high probability you’ll also catch a protest or rally, because Madison). Check out the free Madison Zoo or head north to the Olbrich Botanical Gardens. If you’re into art stop by the Chazen Museum of Art or the Madison Museum of Contemporary Art.

Where to eat:

6. Kalamazoo, Mich. – Distance from Chicago: 150 miles

Besides having the coolest name in Michigan, Kalamazoo is also notable for having a burgeoning foodie and beer scene. This little industrial city has more than a dozen craft brewers.


Where to stay: The Kalamazoo House Bed and Breakfast is an adorable escape right in the middle of downtown. Otherwise, Kalamazoo has a number of affordable chains peppered around the city.

What to do: We’re sending you to Kalamazoo for the beer. Of course, you’ll make Bell’s a priority but don’t skip out on Arcadia Brewing Co., Boatyard Brewing Co., One Well Brewing Co., Gonzo’s BiggDogg Brewing, and Tibbs. As for non-beer activities be sure to make time for Air Zoo which features “50 rare and historic aircraft, amusement park-style rides, Full-Motion Flight Simulators, and RealD 3D/4D Missions Theater.”

Where to eat: Many of the breweries mentioned above have kitchens, but here are other options for eating around Kalamazoo.

  • Brunch: Kzoo has a surprising number of places to grab brunch. Recommended: Coexist Cafe or Crow’s Nest.
  • Dinner: Bold has a delicious selection of small plates. Standouts include the lollipop lamb chops, risotto fritters or the shrimp remoulade. Rustica is Kalamazoo’s destination restaurant. The Roasted Maple Leaf Farms Duck Breast and Braised New Zealand Lamb Shank are must eats.
  • Dessert: Sweetwater’s Donut Mill would give any Chicago donutmaker a run for their money. The Spirit of Kalamazoo is where you want to go downtown for ice cream (and Kalamazoo themed merchandise).
  • Drinks: See “what to do.”

7. Indianapolis, Ind. – Distance from Chicago: 183 miles

Indianapolis is Indiana’s state capital. This is the birthplace of Kurt Vonnegut and home to Kurt Vonnegut Memorial Library. The city has more monuments to veterans and war dead than any other city outside of Washington, D.C.

IndianapolisWhere to stay: If you want a unique experience then check out the Stone Soup Inn. This charming home features 10 rooms with slightly varied themes. The Victorian Room, as the name implies, is decked out in high Victorian style. Also, consider the castle-like Inn at the Villa.

What to do: Take in the arts by visiting the Kurt Vonnegut Memorial Library, the Indianapolis Museum of Art, the Eiteljorg Museum of American Indians and Western Art, or the Indianapolis Art Center. Rent a bike and ride the Indianapolis Cultural Trail. If you’re into alternative sports stop by the Indianapolis Speedway and jump in a two seater car and whip around the track like a pro. If you’re into music be sure to stop in at The Rhythm! Discovery Center where you’ll learn about all things percussive.  Head to Eagle Creek Park and take advantage of the tree top obstacle course at Go Ape.

Where to eat:

  • Brunch: Honestly, you can’t visit Indy and not go to Love Handle. The menu changes daily, but you’ll be happy no matter what’s cooking. In the market for a dutch baby? Hit up Milktooth. Another perfect brunch option is Cafe Patachou which bills itself as “a student union for adults.”
  • Lunch: You’ll want to stop in for a beer at Bent Rail while in town, so why not combine it with lunch? If you’re looking for local pizza it’s hard to go wrong with Indianapolis pizza chain Greek’s Pizzeria. If you love meatballs you’ll want to seek out Mimi Blue where you can choose from a selection of six different meatball types and nearly a dozen sauces.
  • Dinner: It’s hard to go wrong with Mesh on Mass featuring selections from both the land and the sea. Or head to Cobblestone and cross your fingers that the “must-try” chicken involtini (with smoked mozzarella) is on the menu. Open Society has the 16 oz Bone-In Duck Fat Confit Chop you didn’t know you’ve been craving.
  • Dessert: For chilled desserts head to Wyliepalooza. If you want cupcakes you’ll want to find The Flying Cupcake. And sweet crepes can be found at 3 Days in Paris.

  • February 25, 2018