5 Best Weekend Getaways Near Chicago For Every Traveler

Sometimes we all need a break from the urban chaos, so we whipped up the best weekend getaways near Chicago and included hotels in each destination.

Few destinations can stand up to Chicago, but sometimes we all need a break from the concrete, crowds, and traffic. Some prefer the relaxing vibe of small-town charm, others an escape into the great outdoors, or perhaps a little of both.

With this in mind, we consulted with current and former Chicago residents, pulled out our maps, and mixed it all up in our super scientific trivago lab and came up with the best weekend getaways near Chicago.

Chesterton, Indiana — 47 Miles

Photo courtesy of @garethpon

If you’re planning a road trip to Chesterton, Indiana, you’ll want to make sure you’re there by Saturday morning when the town hosts a weekly (from May through the end of October) family/artisanal European Market.

For the afternoon, head over to the Indiana Dunes State Park where you have access to hiking trails (including the nine-mile Calumet Trail), camping, and a number of events, like Beach Yoga, critter feeding, and an “edibles walk” where you learn what you can eat along the trails—meaning no more hangry fights with your significant other who forgot to bring a snack.

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Hotels & Vacation Rentals - Chesterton

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Where to Stay in Chesterton

You get bang for your buck at the Best Western Indian Oak in Chesterton, but there are opportunities to splurge a bit if you like. Rooms can come with a fireplace, a balcony, a spa, and even adjoining rooms if you’re traveling with a large group or family.

Indian Oak also offers massage service, a steam room, an indoor pool, hot tub, and exercise facilities. Hungry? You’ll find Gelsomo’s, an Italian restaurant, right across the street with other nearby restaurants covering everything from Mexican to Thai.

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Best Western Indian Oak

8.4 Very good (1977 reviews)

Lake Geneva, Wisconsin — 80 Miles

Photo courtesy of @grand_geneva

Locals say it’s easy to fall in love with Lake Geneva, pointing to the diversity of opportunities packed into the town of about 8,000. One of the more popular adventures for weekend getaways and road trip travelers from Chicago is the canopy tours. Lake Geneva Canopy Tours will get you out on the ropes year-round for a canopy course with eight different zip-lines covering 100 acres. Prefer staying closer to the ground? They’ve also got nine miles of hiking and mountain biking trails.

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Hotels & Vacation Rentals - Lake Geneva

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Where to Stay in Lake Geneva

You’ll want to call the Grand Geneva Resort & Spa home by the time you’re done with your stay. The AAA Four Diamond resort has everything you could possibly want in a pampered weekend getaway from Chicago. Rooms come equipped with flat-screen televisions, a minifridge, coffee maker, and a writing desk should you be so compelled to jot down some memories.

If you’re one to earn your relaxation, there are tennis courts, two golf courses, and skiing facilities (if it’s the season) where you can work up a sweat. Then, switch right back into relaxation mode by heading to the spa and melting away at one of the property’s pools before dinner and partying it up at the nightclub.

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Grand Geneva Resort and Spa

Lake Geneva
8.4 Very good (2299 reviews)

Starved Rock State Park — 94 Miles

Photo courtesy of Starved Rock Lodge & Conference Center

Look through a gallery of images from Illinois’ Starved Rock State Park and you’d never guess it’s just 90-minutes outside of Chicago. Although you can walk for miles on end across the Wind City, there’s no substitute for the crunch of the trail, and at Starved Rock, you’ve got 13 miles-worth waiting for you around the Illinois River and the seasonal waterfall at St. Louis Canyon. You can also sign up for a canyon tour for $25/person that will take you for a scenic stroll to Council Overhang and Ottawa Canyon.

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Hotels & Vacation Rentals - Oglesby

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Hotel Near Starved Rock

Brightwood Inn is situated conveniently just four minutes (by car) south of Starved Rock State Park and within the confines of Matthiessen State Park. This B&B is perfect for a romantic getaway or even for travelers simply looking for a bit of peace and tranquility surrounded by the serenity of the wilderness. Brightwood makes it easy to relax with your in-room hot tub, fireplace, and a homemade breakfast every morning. They’ll also help you get your heart pumping with state park trails, canoeing on the Fox River, horseback riding, skydiving, cycling on the I&M Canal towpath, and white water rafting on the Vermillion River.

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Brightwood Inn

Top rated
8.9 Excellent (11 reviews)

Saugatuck, Michigan — 142 Miles

Photo courtesy of @kasonjent

Freshwater beaches, natural serenity, and a creative art community encapsulate Saugatuck, Michigan. You might not know much about it, but travel media have long taken note of this region with Condé Nast Traveler crediting Saugatuck with one of the “Top 25 Beaches in the World” where travelers can find a secluded stretch of sand and take in an awe-inspiring sunset.

More active travelers can work their way through rolling dunes or, come winter time, go cross-country skiing along the frozen shore or in the snow-covered woods. Once you’ve inevitably worked up an appetite, the plethora of locally-sourced restaurants and neighborhood coffee shops are there to energize you before you head back into the wild.

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Hotels & Vacation Rentals - Saugatuck

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Where to Stay in Saugatuck

At Hidden Garden Cottages & Suites, you get privacy and convenience. Located right in the heart of downtown Saugatuck, everything you could possibly need is within walking distance — and we’re not just talking about restaurants. Oval Beach is under a mile away as well as Mt. Baldhead Park and the Saugatuck Harbor Natural Area. When you’re at the Inn, you’ll be treated to 27 years-worth of hospitality with a number of package specials available for a little icing on the cake on your weekend getaway.

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Hidden Garden Cottages & Suites

Top rated
9.0 Excellent (218 reviews)

Sheboygan, Wisconsin — 148 Miles

Photo courtesy of @eossurf

More Lake Michigan fun awaits in the Wisconsin town known as “The Spirit on the Lake.” Bonus points for holding claim as the bratwurst capital of the world. Need proof? Head to the Old Wisconsin Sausage Outlet Store, a local favorite for over 50 years. Needless to say, you’ll need to make the most of the outdoors to burn up those bratwurst calories and Sheboygan does not disappoint.

The lake itself offers surfing, kite surfing, windsurfing, sailing, kayaking, jet skiing, boating, and fishing. By land, you can bike, hike, climb, and golf before celebrating your healthy excursions with more food and drink. Then again, Sheboygan also keeps more zen-like travelers in mind with spas to relax the body.

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Hotels & Vacation Rentals - Sheboygan

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Where to Stay in Sheboygan

Right downtown and steps away from Lake Michigan, you’ll find one of the town’s highest guest-rated hotels in GrandStay Sheboygan. No matter what you book, you’ll get a full kitchen and a number of modern amenities in this pet-friendly hotel. If you’re staying for a few nights, you’ll have to take advantage of the indoor pool & whirlpool and exercise room.

Need help finding your way around? GrandStay Sheboygan can point you in the right direction of restaurants, shopping, nearby attractions, and upcoming events, like the annual Dairyland Surf Classic—the globe’s largest lake surfing competition.

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GrandStay Hotel & Suites Downtown Sheboygan

Top rated
8.6 Excellent (1757 reviews)

Featured image courtesy of Aaron Burden on Unsplash