Chicago Day Trips

How to get there using Google Maps

Evanston

14 miles. About 25 minutes
(from State & Madison intersection)

Accessible via CTA and Metra

Evanston is ostensibly a suburb, given the fact that it's about a 30 minute drive north of downtown Chicago, but this cozy town is certainly it's own.

It's the perfect place for a weekend getaway that's not really that far away. The town, which houses prestigious Northwestern University, is loaded with boutiques, progressive restaurants, cafes and has some beautiful homes and a quaint downtown. We love too many restaurants here to list, but The Stained Glass, Space and Jilly's are my favorites.

There's some great art at the Mary and Leigh Block Museum of Art. And I stumbled across the cute Shakespeare Garden, which immediately became one of my favorite spots in all of the Chicago area. I loved my stays at the Margarita European Inn and the Orrington Hotel.

How to get there using Google Maps

Naperville

29.9 miles. About 31 minutes
(from State & Madison intersection)

Accessible via Metra

Another far flung Chicago "suburb" that was much much more than just a place for urban sprawl during the early 1900s. And while the area has been overrun with strip malls and retail chains, it's managed to retain much of its original character.

And when we spent a weekend there a couple months back, we tried to soak as much of that in as we could. It started with going for a walk in the Riverwalk downtown, which was quiet and pleasant. Our first night out we had dinner at the Naf Naf Grill, a Middle Eastern restaurant that has a reputation beyond the Chicago area. We took the kids to Odyssey Fun World to play some video games and later checked out the Comedy Shrine, which was entertaining even for our teenagers.

The visit we took with the kids we stayed at the Wyndham in nearby Lisle, but when we went back for a Saturday night getaway with just the two of us, we got a great room at the lovely Harrison House Bed & Breakfast.

How to get there using Google Maps

Schaumburg

30.6 miles. About 55 minutes
(from State & Madison intersection)

Accessible via Metra

To some, Schaumburg is a punchline. If you're from the city and one of your friends tells you they're moving there, the joke is they might as well be moving to Timbuktu, because you'll hardly ever see them again. But maybe that's not really as true as most from the city think. Schaumburg does have some things going for it these days, namely the best shopping mall in all of Chicagoland; the Woodfield Shopping Center.

Woodfield has everything a shopper would want. And there's also a Medieval Times, which admittedly is one of the most ridiculously themed forms of entertainment in the United States, but it's fun checking out if only for the joke. We had quite a bit of fun there, actually. As far as hotels go, there's not a lot of unique places.

Both times I've stayed there, I had rooms at the Quality Inn Elk Grove and the Chicago Marriott Schaumburg. Another thing that Schaumburg has going for it is one of the best comedy clubs in the area - one that actually rivals its city counterparts - the Improv Comedy Club. Lots of laughs there. We had some great, affordable sushi at Sushi Ya, and some great Indian food at the Saffron Restaurant.

How to get there using Google Maps

Saint Charles

39 miles. About 1 hour
(from State & Madison intersection)

Accessible via Metra

Just far enough outside of Chicago to make it feel like a genuine getaway. But at roughly 40 miles away, the drive won't take too much out of you. It's one of our favorite weekend getaways because we can be back home within an hour most weekends. The main draw of the place is its cozy old fashioned town atmosphere, which starts with the Hotel Baker, which is where we usually stay when we go. It's right on the banks of the Fox River that runs through town. We've also spent a lot of time at the Pheasant Run Resort, a sort of ‘wanna be’ Mardi Gras themed hotel.

Perusing the aisles of Town House Books is always a good way to spend a couple hours; we always end up finding some unique buys there. We also toured the Fox River via a St. Charles Paddlewheel River Boat, which is the best way to explore the quaint river.

We checked out a concert at the Arcadia Theater, a throw-back movie house that books all sorts of shows these days. We dined at Francesca's by the River, which isn't actually that close to the river, but it's got some great food. We had after-dinner drinks at the Beehive, a cozy neighborhood bar and grill.

How to get there using Google Maps

Waukegan

41.4 miles. About 48 minutes
(from State & Madison intersection)

Accessible via Metra

Waukegan is ostensibly one of the largest suburbs of Chicago, as it's the ninth largest city in the state of Illinois, but it's honestly very much its own city. It's located right near the Illinois- Wisconsin border, which makes it roughly a 45 minute drive from downtown Chicago if the traffic's light.

It's a very working-class town, located right on Lake Michigan, but the place has some truly unique stops. Namely Horsefeathers Inc., a unique bohemian nick-nack store. There's also the Waukegan Harbor House, an affordable Lake Michigan charter boat (which is much cheaper than its Chicago counterparts). The Brunswick Zone-Lakehurst is one of the area's largest and most unique bowling alleys, and the Sundance Saloon is one of the more "interesting" clubs on the North Shore.

The Sweet Basil Hill Farm Inn is a great, affordable place to get a bed and breakfast room. And two quirky restaurants we grabbed some grub at were El Famous Burrito and Ming Toy Restaurant, a hole-in-the-wall Chinese joint.

How to get there using Google Maps

Aurora

41.9 miles. About 43 minutes
(from State & Madison intersection)

Accessible via Metra

Aurora , Ill., may be best known as the dull hometown of the guys from Wayne's World. But that was back in the 1990s. Since then the town's managed to carve out a niche as a destination for Chicagoans looking to get out of the city but not spend three hours in a car (the town's about a 50 minute drive from downtown Chicago). As far as hotels go, there aren't a lot of unique choices. Your best bets are the Hampton Inn and the Candlewood Suites (both chains, sadly).

But if you're with kids, you can't get too fancy. Two great destinations for the young and old, we discovered, are the Sci-Tech Hands-on Museum and the Aurora Skate Center, which the whole family had fun at. We had a great breakfast at the Blueberry Hill Pancake House, and took in some comedy, a light dinner and some micro brews at Walter Payton's Roundhouse (which was started by the late legendary Bears running back). The unique historic building provides for a great sports watching environment.

We got away from the kids for a couple hours and a had a splendid dinner at Chef Amaury Epicurean Affair, one of the better fine dining experiences I've had. On Sunday, we let the boys watch some football at the Foundry while we did some shopping.

How to get there using Google Maps

Geneva

46.1 miles. About 51 minutes
(from State & Madison intersection)

Accessible via Metra

Considered a suburb technically, but it's really a historical city that stands out on its own. It's full of unique shops, bed and breakfasts and locally-run restaurants and shops.

Our visit there included a stop at the breathtaking Fabyan Forest Preserve for some nature-seeing and some shopping at Cocoon, a great vintage shop.

We also checked out some art at Gallery 28 and did some sweet shopping at Sweet Nostalgia, an old fashioned candy store. Our most memorable dining experience was at Foxfire, a great steakhouse. We stayed at the Herrington Inn & Spa and The Oscar Swan, a bed and breakfast.

How to get there using Google Maps

Joliet

47.4 miles. About 47 minutes
(from State & Madison intersection)

Accessible via Metra

Joliet, Ill., is a working class town if there ever was one. Located 40 miles south of Chicago, it was long home to many manufacturing companies. Many of those companies have left, forcing the city to diversify itself both in its workplace and its residents, seeing many new transplants from Chicago.

The city is undergoing a renovation of much of its downtown, which features the Joliet Area Historical Museum. The Empress Casino Joliet is also a big hit for out-of-towners that don't live near a casino. There's surprisingly some really great food in Joliet, namely Truth, and Hey Hot Dog. The Ven-U is one of the better music clubs in all of Illinois.

Chester Manor, which is in nearby Wilmington, is a lovely bed and breakfast that's an easy drive from Joliet. Dellwood Park, which is nearby Lockport, is nearly a century old. It's a great place to spend a lazy afternoon.

How to get there using Google Maps

Kenosha

57.3 miles. About 57 minutes
(from State & Madison intersection)

Accessible via Metra

Kenosha's the first decently sized city you hit in the state of Wisconsin if you head north of Chicago, and it's also one of the last stops on the Metra train (which services Chicago and its suburbs), so you can get to and from this town without even needing a car. Though if you do drive, it takes no longer than an hour to get there.

The best draw to this town is its easy access to Lake Michigan, which is evidenced by the great lakefront hotels and marinas. Namely, the Best Western Harborside Inn and the Southport bed and breakfast, which are both right on the water.

There are also some great museums such as the Kenosha Public Museum and the Anderson Arts Center. And one of the more unique stops in Kenosha is the Jelly Belly Center, the jellybean factory just outside of town. We had a great dinner at Lazybird, and had some of the best greasy diner food I've ever had at Franks Diner.

How to get there using Google Maps

Harbor Country

70.8 miles. About 1 hour and 11 minutes
(from State & Madison intersection)

The main draw to Harbor Country in southwestern Michigan is the sand dunes at Warren Dunes State Park. On a really clear day, you can climb on top of them and off in the distance 70 miles to the west, you can see the Chicago skyline. There's also some great swimming on these beaches.

Aside from the dunes, we checked out the Round Bar Winery, considered one of the most unique wineries in Michigan. We caught a concert at the eclectic Acorn Theater, a converted old corset factory.

We grabbed some meat for grilling out at Drier's Old Fashioned Meat Market and picked up some fruit at Jackson's Fruit Stand. We stayed at the Frank Lloyd Wright inspired Harbor Grand Hotels and Suites, and also spent a night gambling at the Four Winds Casino.

How to get there using Google Maps

Racine

77.9 miles. About 1 hour and 23 minutes
(from State & Madison intersection)

For many, Racine, Wis., is merely a stopping point between Chicago and Milwaukee. Many don't think of it as a bona fide tourist attraction, which is a shame, because it's an extremely cheap (and, considering it's just over an hour north of Chicago; easy) destination.

It's home to one of Frank Lloyd Wright's loveliest designs, the Wingspread. You can't sleep in Wingspread, but you can stay at a great bed and breakfast in the Hughes House Bed and Breakfast.

The Racine Art Museum is small, but packs a punch. Lots of Great Depression era artwork there. Kewpee Lunch and Hobnob Restaurant are great small town-ish restaurants. And Paul's Video Arcade is one of the few true video arcades that's left (or at least that I've found). It's a real gem.

How to get there using Google Maps

Rockford

88.8 miles. About 1 hour and 30 minutes
(from State & Madison intersection)

Accessible via Amtrak

People go to Rockford, which is a little more than an hour outside of the city, primarily for the museums and gardens: Anderson Gardens is one of the most unique gardens in the state of Illinois.

The Klehm Arboretum, Discover Center Museum, Burpee Museum of Natural History and Tinker Swiss Cottage Museum are also great visits.

The best restaurant we ate at in town was the Pearl Bistro, and we got a great room at the Baymont Inn and Suites.

How to get there using Google Maps

South Bend

95.6 miles. About 1 hour and 34 minutes
(from State & Madison intersection)

Accessible via Amtrak

Known nationally as the home of the University of Notre Dame. And honestly, little else. Which is sad, because this tiny working class town actually has a lot to offer outside the prestigious university.

Of course, the main attraction here is Notre Dame football, and while it's optimal to visit while the Fighting Irish football team is in town, if you're there in the off-season, it's still worth checking out historic Notre Dame Stadium.

South Bend is also the home to the College Football Hall of Fame, as well as a handful of obscure museums like the RV/MH Hall of Fame and the Studabaker National Museum, must sees for any car enthusiast. When we're not feeling sports-y, we check out the Circa Arts Gallery. There's a number of cozy bed and breakfasts, our two favorites being the Innisfree Celtic Bed and Breakfast and the Oliver Inn B&B.

There's plenty of bar food in South Bend, but if you want a good meal, try Elia's and The Vine or Indulgence pastry shop & café.

How to get there using Google Maps

Champaign

138 miles. About 2 hours and 11 minutes
(from State & Madison intersection)

Accessible via Amtrak

Champaign, Ill., is home to the largest state university in the state of Illinois, and it's considered one of the better (and largest) college towns in the Midwest.

It's a pretty easy couple hour drive south from Chicago. And there's no shortage of things to do. I've always enjoyed myself on trips to the town over the years, especially the bar scene – the Blind Pig Company is my favorite. I usually grab some grub at Ecsobar's or Zorba's Restaurant. To get my art fix I usually visit Boardman's Art Theater and the Krannert Art Museum. I usually pay a visit to Curtis Orchard. Both the Historic Lincoln Hotel and The Avenue Bed & Breakfast are two of my favorite hotels/B&Bs in all of Illinois.

How to get there using Google Maps

Madison

148 miles. About 2 hours and 21 minutes
(from State & Madison intersection)

Accessible via Amtrak

Known as one of the craziest party college towns in the country, but it's much, much more than that. It's also a cultural hotbed loaded with unique, locally-run businesses. One of our favorite draws is the Madison Museum of Contemporary Art, which pound for pound, is as good as any contemporary art museum in the US. We usually like to make a visit to the State Street Gallery before or after hitting up the MMCA.

Madison has a lot of knick knack shops downtown, but Pop Deluxe is the most refined. It's such a beautiful landscape, that you can't help but want to spend some time outside, so we hit up the Henry Vilas Zoo, a rare non-profit zoo that was a ton of fun. We stopped off at Genna's Lounge for some super cheap happy hour drinks, had some great Mediterranean food at Husnu's and some great locally-made pizza at The Roman Candle Pizzeria. We got a wonderful room at the eco-friendly Arbor House, that was surprisingly cheap considering all its amenities.

How to get there using Google Maps

Galena

164 miles. About 3 hours and 18 minutes
(from State & Madison intersection)

One of the best well-kept old fashioned little towns in the entire country. Just three hours west of Chicago, it's a massively popular tourist destination for Chicagoans looking to get away from the hustle and bustle of city life. It's known for its spectacular turn of the century homes, and they were the highlight of our trip there.

We visited the historic Dowling House and Belvedere Mansion and Gardens, which are two of the finest estates in town. We spent an afternoon at the Linmar Gardens, a century-old flower garden. We spent some time at the Galena Cellars Winery, which was very quaint. We had some drinks at Miss Kitty's Grape Escape, a cute little wine bar owned by a spunky Chicago transplant.

Our top dining experiences were at Fritz & Frites, a unique German/French bistro, and Fried Green Tomatoes, a kitschy Italian/American joint. We stayed at the Farmer's Guest House, a cute, cozy bed and breakfast.

How to get there using Google Maps

Peoria

168 miles. About 2 hours and 40 minutes
(from State & Madison intersection)

Accessible via Amtrak

If you could draw up an average American city, it'd probably look a lot like Peoria, Ill. But don't take this town of just over 100,000 that's roughly three hours south of Chicago as being too ordinary. It's got an identity; from some hopping college bars/restaurants to historic hotels and landmarks.

We got a room at the vintage Randolph Terrace Inn, a delightful and affordable bed and breakfast. We checked out the cheap Glen Oak Zoo, then grabbed an ice cream cone at the old fashioned Emo's Dairy Mart. The highlight of our trip, I would say, was the river boat trip we took on the Spirit of Peoria, an authentic paddle-wheeler steamboat.

We had two superb dining experiences: the German Peoria Hofbrau and Sizzling India (my favorite of the two; surprisingly some really great Indian food in a town not exactly famous for it). We spent Saturday night at Martini's on Water Street, probably the most upscale bar in town.

How to get there using Google Maps

Dubuque, Iowa

179 miles. About 2 hours and 43 minutes
(from State & Madison intersection)

It isn't the first town you think of if you're looking to take a day trip from a big Midwestern city. Even people in small towns probably don't think much of this old river town - the oldest in the state of Iowa - that's seen some rough times over the last half decade.

But it has some gems, most notably the National Mississippi River Museum and the Fourth Street Elevator. There's also a surprisingly great restaurant in Pepper Sprout, which features standard American fare.

I had a great room at the historic Hancock House Bed and Breakfast and also had some great Italian food at Mario's Italian Restaurant and Lounge. Other highlights include the Dubuque Museum of Art and Crystal Lake Cave.

How to get there using Google Maps

Wisconsin Dells

195 miles. About 3 hours and 4 minutes
(from State & Madison intersection)

Accessible via Amtrak

The Wisconsin Dells, roughly three hours from Chicago, have a reputation for being a tourist trap, and it pretty much is. So while maybe it's not always the best place for a getaway for adults, the kids love it. I know I did when I was younger. The place deems itself the water park capital of the world, and I have to imagine it is. We went later in the fall, so we stayed at the Kalahari Resort, which offers a massive in-door water park, which was a great winter getaway.

Of course, when you go to the Dells, you've also got to see the actual Dells on the scenic Wisconsin River. The best bet to view them is via the Dells Ducks, which offer tours in old WWII army ducks and souped up speed boats. Great way to spend a couple hours viewing some amazing geological formations along the river.

We did some great mini-golf playing at Pirate's Cove, which offers five different 18-hole courses. In an attempt to save as much money as we could, we prepared as many of our own meals as we could at the hotel. It can get really expensive feeding a family by eating out every day. But we did try two different restaurants: Moosejaw Pizza and Paul Bunyan's, both local mainstays. We also took a tour of the grand Al Ringling Theater, a historic movie house from the early 1900s.

If you visit the Dells area in wintertime, you have the added attraction of alpine skiing at Cascade Mountain. One of the largest skiing destinations within a three hour drive of Chicago, Cascade offers fun for the whole family, including lessons and “kids ski free” options. With a myriad of choices, including skiing, snowboarding, and snow tubing, everyone is sure to find something they’ll enjoy. There are food and drink options on site, including the Peak Bar, which is a great place to grab a warm drink and watch the action from the large picture windows. If people in our group tire early, this is where we all meet back up. Cascade is a great “all ages” option – we’ve gone with groups of college friends, and with the family ranging in age from under 10 to over 60, and always had a wonderful time.

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Appleton

196 miles. About 3 hours and 7 minutes
(from State & Madison intersection)

Accessible via Amtrak

At just 200 miles from Chicago, Appleton, Wis., is a little-known retreat from the city. It may not be quite as heralded as the Dells, Madison or some of the Lake Michigan getaways, but this decently-sized town sits on the shores of the lovely Lake Winnebago, one of the largest lakes in the state of Wisconsin.

The bed and breakfasts are the highlights here. Two of the best ones I've ever been to are here: The Roost and the Quilt'n'Be, which were both lovely.

The Fox Cities Performing Arts Center is one of the largest of its kind in the area. We went on a great trolley tour through the historic parts of town on the Downtown Cool Trolley, and had great meals at Apollon and Frank's Pizza Palace, which we really, really enjoyed. Enchanting vintage atmosphere that was lots of fun. And Dr. Jekyll's has so much character, you'd think it was in a much, much bigger city.

How to get there using Google Maps

Springfield

200 miles. About 3 hours and 12 minutes
(from State & Madison intersection)

Accessible via Amtrak

The state's capitol is roughly two and a half miles due south of Chicago and offers numerous attractions, most of which are former President Abraham Lincoln-related.

There's the prestigious President Abraham Lincoln Hotel & Conference Center, where you can get a cheap room right next to many Lincoln-related attractions.

There's the Washington Park Botanical Garden and Henson Robinson Zoo for outdoor enthusiasts. Architecture fans should stop by the Frank Lloyd Wright Dana-Thomas House and music buffs will love Penny Lane Gifts. The Muni is regarded as one of the best non-profit theater companies in the state, and The Beach and Knights Action Park and Caribbean Water Adventure are perfect summer getaways.

How to get there using Google Maps

Green Bay

205 miles. About 3 hours and 17 minutes
(from State & Madison intersection)

Accessible via Amtrak

They call Green Bay, Wis., Title Town because of all the professional football championships the Green Bay Packers won in the 1960s. But the tiny town three-and-a-half hours north of Chicago has grown up a lot over the years, yet still managed to maintain the charm that comes with being one of the smallest towns in America to host a professional sports franchise. The draw here is football, for obvious reasons.

But this little town has much more to offer, starting with two great places to spend the night; the old fashioned St. Brendan's Inn, and the Astor House, a cozy bed and breakfast. We did some gambling at Oneida Bingo & Poker, and caught a cheap second-run movie at the De Pere Theater, a throwback of a movie house if there ever was one.

We dined at Kavarna, a really unique vegetarian-themed place, and had a great bowl of chili at Chili John's. And of course, no visit to Green Bay is complete without checking out the Packers Hall of Fame, which is historically fascinating enough to keep the attention of even the mildest of football fans.

How to get there using Google Maps

Fort Wayne

205 miles. About 3 hours and 13 minutes
(from State & Madison intersection)

At roughly three hours from Chicago, Fort Wayne isn't always the first destination that people think of for a great weekend escape, but the town of roughly 250,000 does have a lot going for it. Namely, a couple great restaurants: Henry's, and Loving Cafe, which was one of the best vegetarian place I've eaten at. We found a great punk rock club in the Brass Rail and really enjoyed the Fort Wayne Museum of Art.

Our room at the Worthington Mansion was matched in excellence by the breakfast we had one morning, and just before leaving town we hit up the Coney Island Weiner Stand, which we were told was a must-visit while in Fort Wayne.

How to get there using Google Maps

French Lick

317 miles. About 5 hours and 31 minutes
(from State & Madison intersection)

French Lick, Ind., is known for mainly two things: being the home of basketball legend Larry Bird and being one of the most well-maintained vintage towns in the United States. The town, located roughly 300 miles southeast of Chicago, is laced with beautiful Victorian homes, boutiques, cafes and bed and breakfasts.

And Marengo Cave is one of the most amazing caves I've ever seen. We spent a day in the sun at the Big Splash Adventure water park with the kids, and on a second trip there a while back with just the adults, we stayed at the quaint West Baden Springs Hotel and had an amazing meal at Sinclair's Find Dining in nearby West Baden Springs.

How to get there using Google Maps

Michigan's Upper Peninsula

320 miles. About 5 hours and 20 minutes
(from State & Madison intersection)

Michigan's Upper Peninsula is one of the most beautiful places in the Midwest. And it's about as far away from society as you can get in this part of the country. You're really up in the UP (as locals refer to it).

Near Canada, in fact. One of the top towns to visit in the UP is Traverse City, a historical old town that is roughly five hours from Chicago. When we go we usually stay at the smoke-free Bayshore Resort.

We've also stayed at the Chateau Chantal, a warm and welcoming bed and breakfast. Our favorite dining spots are The Cook's House, which does some really adventurous dishes at a reasonable price, and Poppycocks, which is a great, cheap lunch spot. We love perusing the works at the Artcenter, and usually try to hit an art-house flick at the historic State Theater. No trip to Traverse City is complete without a visit to the Duncan I. Clinch Marina is a great choice too, which offers some of the best water views in the area, as well as some amazing boat watching.

How to get there using Google Maps

Des Moines

332 miles. About 5 hours and 9 minutes
(from State & Madison intersection)

Des Moines, Iowa, is an easy town to brush aside. You can drive through this place a hundred times and not think there was anything unique going on here. But you'd be mistaken. For this capital city of the state of Iowa, which is roughly a five hour drive from Chicago, has come a long way in the last ten years.

For starters, there are some great places to get rooms: The Hotel Fort Des Moines and the historic Butler House on Grand, which is one of the best bed and breakfasts in the entire state.

No visit to Des Moines is complete without a visit to both the Des Moines Botanical Center and the Des Moines Art Center, both of which are comparable to facilities in much larger cities. We caught a cheap movie at the old fashioned Fleur Cinema & Cafe and also really enjoyed the Ritual Cafe, a cozy locally-run coffee shop. We had our best meal at the progressive Flying Mango restaurant, which had lots of adventurous dishes such as dried apricots with goat cheese and pistachios.

How to get there using Google Maps

Carbondale

332 miles. About 5 hours and 18 minutes
(from State & Madison intersection)

Accessible via Amtrak

Carbondale, Ill. houses the campus of the University of Southern Illinois, which is roughly five and a half hours due south of Chicago.

The highlight of the town is the historic university, which has been around for half a century. The university's museum has an eclectic collection of art, history and geology. It's also home to an outstanding sandwich shop (Booby's) and some great bars, the best of which is PK's.

We stopped in the 710 Book Store to look for some books and SIU apparel. We also passed the supposedly haunted Hundley House in the middle of town.

Have a nice trip!