The 9 Best Weekend Getaways From Chicago

April 30th, 2014
The 9 Best Weekend Getaways From Chicago

We love our fair city but sometimes all the noise, traffic, politics and people make us feel a little anxious, craving for a change of scenery just for a few days. Thankfully we’ve got plenty of options for weekend getaways that are just a short trip from Chicago.

We shared some of our favorites last year and added even more this time around. Whether you crave nature, a relaxing weekend of wining and dining or just a different skyline to enjoy, we share some of our favorite spots to check out the next time you feel a bit restless in the city.

Union Pier & Three Oaks Michigan
Sometimes you just need a breath of fresh air and a slightly slower pace compared to the daily hustle of life in Chicago. But if I’m heading outside the city for the weekend, I want to maximize my relaxing and minimize my travel time. Just less than 1.5 hours away right across the border of Michigan I’ve found the perfect spot to spend the weekend relaxing by a fire, soaking in a hot tub and enjoying a bottle of local wine. Union Pier is one of the many small communities right on the edge of the Michigan and Indiana border that are close enough to each other to drive and explore. I enjoy staying at the Sweethaven Resort in Union Pier. It’s right off the highway and a quick walk or bike ride down to the beach. It’s also just down the road from Round Barn Winery so stop in and grab a bottle of cherry wine on your way to your cabin. Sweethaven is ran by a lovely couple who make sure you have everything you need for your stay. Most of the cabins have private hot tubs which is the perfect place to relax and enjoy that cherry wine you picked up. Pick up a thin crust pizza from Mario’s and tuck in for a night by the fireplace with a good book.

After an evening of relaxing, spend the next day doing two of my favorite pastimes; drinking and eating. Round Barn has a great tasting room with a large selection of their wines, spirits and beer. And if you do a tasting they offer a discount on purchases. Next drive over to neighboring town Three Oaks and enjoy lunch at Pleasant House. These Bridgeport royal pies have many fans in Chicago and their second location also offers their own beer selections. My favorite meal to order is their chicken balti pie, flakey buttery crust packed with curry spices and chicken, some mash and buttered peas with mint. Afterwards head over to Journeyman Distillery just around the corner and grab a tour of the facility. At the end try some of the spirits they offer, grab a few bottles (my personal favorites are their Silver Cross whiskey and their Snaggle Tooth coffee liqueur) and then head to the bar for a seasonal cocktail or two. It’s nice to find a place so close to the city that still feels like a true getaway. — Lisa White

Union Pier And Three Oaks (Part of the Harbor County region) are located about 75 miles Southeast from Chicago off I-94.

Even if you don’t like to drive you can have a stellar weekend getaway in this Kane County town as it’s a quick Metra ride from Chicago. Spend a day or two checking out Geneva’s restaurants like Niche, Preservation Bread & Wine, Nobel House and The Sugar Path. There’s plenty of lodging available for a last-minute trip and shopping to burn a hole in your budget. But the main reason I’m dying to visit Geneva is to spend a day at the newly opened Penrose Brewing Co. Spending a weekend at their tap room and taking a train back to Chicago seems like a sound, common-sense idea. —Chuck Sudo

Geneva, Ill. is located 42 miles west of downtown Chicago and is accessible via Metra’s Union Pacific West Line.

While some like to escape the big city for weekend getaways, others like to explore other urban areas. Just two hours to our north, Milwaukee is an excellent option. A Rust Belt town that hasn’t kept pace with Chicago, an urban vibrancy is developing across the “Cream City” still most well known for beer and motorcycles. Chicagoans are perhaps best acquainted with Milwaukee’s SummerFest, which runs from June 25-July 6 and includes a roster of big name concerts. Don’t miss the Milwaukee Art Museum, whose most impressive work of art is the building itself. Starchitect Santiago Caletrava designed a new wing for the museum in 2001 that soars over the lakefront like a giant white bird. inside the museum is a combination of permanent collections and visiting exhibitions. Harley-Davidson calls Milwaukee home, and the Harley-Davidson Museum should be near the top of the list to visit if you have any interest in Hogs. Dining options include long time standard treats like Kopp’s Frozen Custard, while Alterra’s Colectivo’s (ed. note: Alterra changed their company name to Colectivo. Still the same great coffee!) loft-like Coffee houses dot the city. Standout meals include a visit to HoneyPie for their comfort food favorites and St. Paul Fish Company, in the Milwaukee Public Market, which features a daily $13.95 Lobster Dinner special. Drinking holes include countless taverns and dive bars. Get into the spirit of Milwaukee’s German heritage at Old German Beer Hall, or have a proper Mai Tai at Foundation Tiki Bar.— Benjy Lipsman

Milwaukee is located about 90 miles up I-94 north of Chicago.

Egg Harbor & Door County Wisconsin
We’ve mentioned Door County before, and there’s lots to see, from lighthouses to parks to restaurants with goats on the roof. But while most flock to Sister Bay and its larger siblings, we’d like to humbly recommend Egg Harbor. It’s a quieter town not without its own amenities. Located close to the middle of the peninsula, you can still wander to the larger towns and attractions without much effort. If you do wander, we recommend a dinner out at the small but satisfying Chop steakhouse up in Sister Bay, a pizza or really anything from Wild Tomato, which features wood-fired pizzas and grill items. Explore cheese shops and take a ferry to Washington Island if the mood suits you. The great thing about Egg Harbor is that it’s *not* the center of attention. We loved staying at the Newport Resort. It features apartment-style rooms, with large balconies, fireplaces and in some cases, whirlpool tubs en suite. We found the Main Street Market, which is in walking distance of the Newport, to be a surprising little gem that made us want to stay in and use our kitchenette more. It boasts wonderful produce and local offerings, and just about anything else you might need if you find yourself wanting to dodge the usual influx of tourists and relax for the evening. If you’re staying in town, there’s a small downtown area to wander, and another good dinner pick is Casey’s BBQ Smokehouse. They’ve got an extensive menu, some local Wisconsin watering-hole flair and a view of the lake from a tiny picture window that at sunset will leave you quite sated. If you’re looking for a Door County escape that’s a bit less touristy, we couldn’t recommend Egg Harbor more. –Marielle Shaw

Egg Harbor, WI is a 4 hour trip, 263 miles north of Chicago.

Wisconsin River Canoeing
In need of a back to nature retreat? Ditch the cabins and campgrounds in favor of spending the night on a sandbar along the Wisconsin River. A few different companies will outfit you with canoes or kayaks for a fairly lazy river ride, but I’d recommend Wisconsin Canoe Co. just outside of Madison for day and overnight trips. Be sure to check the river conditions, which can be found on their website, a few days before your trek and reserve your equipment online (don’t forget to include firewood, a dry bag and a cup holder). Take a shuttle to your drop in and you’re left to the devices of the elements, your new river friends and Wisconsin’s only legal public nude beach. — Jessica Mlinaric

Wisconsin Canoe Company shuttles depart from Peck’s Landing located at the intersection of Hwy 23 and the Wisconsin River.

Saugatuck & Douglas Michigan
Saugatuck and the smaller neighboring town Douglas are popular tourist spots for Chicagoans. Just two hours from the city, there’s a ton to do between the beaches, restaurants, art galleries and shopping. Stay in one of their many bed & breakfasts or in a small inn on the shore. There are a bunch of wineries and breweries just a short drive away, including Fenn Valley Vineyards to the south, and New Holland Brewing (try the beer barrel bourbon, you’ll thank us) to the north (they offer tours on Saturdays). Both towns are a hotspot with the LGBT crowd, in fact, if you visit on Halloween weekend be sure to go to the “adult parade” in Douglas. It can get a little racy, but it’s more about the elaborate costumes. Proof that the small towns dotting the shore of southwestern Michigan are fun throughout the year, not just in summer. — Michelle Meywes

Saugatuck and Douglas are located about 140 miles from Chicago in southwest Michigan.

St. Louis
If there’s one good thing that can be said about my hometown of St. Louis it’s that the riverfront city can provide a great vacation on a small budget. A good handful of St. Louis’s most popular attractions are free while others charge only a fraction of which Chicago’s museum’s and touristy spots will cost you. General admission to the St. Louis Zoo, a full day’s worth of entertainment in beautiful Forest Park, is free. Grant’s Farm (named for the land’s former presidential owner) is a 281-acre wildlife preserve that’s also free to the public. I recommend the highly entertaining “Animal Encounters” show if roller-skating parrots are your thing. And for beer drinkers, take a tour of the Anheuser-Busch Brewery downtown. Not only is the tour free, so are the samples.

If you are going to spend money during your stay, save it for the City Museum—truly the most unique attraction St. Louis has to offer—or the city’s booming dining scene. The Shaved Duck is this writer’s current favorite when it comes to STL restaurants. — Katie Karpowicz

St. Louis is 297 miles from Chicago, roughly a 5 hour drive or 6 hour Megabus/Amtrak ride.

Starved Rock State Park

Looking back at last year’s list I’m stunned that Starved Rock was omitted, simply because its 13 miles of hiking trails, scenic waterfalls, sandstone bluff canyons and gorgeous views of the Illinois River have me wondering why more of Illinois can’t be as idyllic as this. Starved Rock is a popular getaway any time of year and easily accessible by car or, if you’re up for a challenge, by bicycle; I’ve done both. Camping enthusiasts flock to Starved Rock when the weather is good and, if you aren’t down for getting completely immersed with nature, the park’s lodge makes for an equally peaceful retreat. —Chuck Sudo

Starved Rock State Park is located in Oglesby, Ill.

Churchill Downs
It is Derby weekend and that’s probably why Churchill Downs is on the brain, but a trip to this historic racetrack is a pilgrimage for any fan of Thoroughbred racing. Although not quite as beautiful as say Saratoga or even as clean and modern as Arlington Park, Churchill Downs continues to attract some of the best trainers and horses in the country for some great afternoons of racing. If you need a break from the action, you don’t have to drive too far east of Louisville to check out some Kentucky bourbon distilleries or tour some nearby horse farms. And if you’re looking to cash some tickets this weekend, focus on the terrific undercard. Hitting the Derby is like hitting the lottery with its huge field of lightly-run horses, none of which have raced a mile and a quarter. Good luck! — Casey Moffitt

Churchill Downs is located at 700 Central Ave. in Louisville, KY.