The 5 best weekend getaways from Chicago

Perched on the lip of Lake Michigan, Chicago is the hunky yet humble centrepiece of the American northwest. As well as being a liberal-minded metropolis packed with diversity, Chicago offers a plethora of weekend getaways, many of which lie no more than three hours’ drive away, based in Illinois, Wisconsin, Michigan and Indiana. While wild jaunts in Chicago are a given, find your feet in the region by escaping the city if only for a night or two. To help you do this, we’ve put together a selection of the best weekend trips from Chicago, from the historic town of Galena and the foodie utopia of Milwaukee to the artsy hub of Saugatuck and beyond.

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Chicago | Photo: Sawyer Bengtson

Chicago 

The lapping waters of Lake Michigan reflect upon the sleek architecture of Chicago, providing the perfect setting for multiple Michelin-starred kitchens and fancy craft breweries. Stick to the downtown loop or live it up along the Gold Coast, whatever you choose, expect to find world-class shopping, coffee, bars and clubs, as well as a vibrant LGBTQ+ scene centred on Boystown and branching into the Nordic world of Andersonville. If you’re keyed in, you’ll plan your trip to Chicago around the annual epic Pride Parade or any of the alternative festivals which run all summer long. Spend a few days getting acquainted with this inclusive gem of a city, before heading off on your weekend getaway. For insights into what to do and where to stay, see our dedicated Chicago travel guide.

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Boasting the ‘Best Main Street in the Midwest’, Galena is sure to charm with its sunset cruises up the Mississippi River and opportunities to tie the knot while flying in a hot air balloon

1. Galena, Illinois

Swap the city asphalt for romantic heritage with a trip to the small town of Galena (accessible via the I-90 West and US-20 West). A superb way to unwind after a week of Boystown antics, Galena is just three hours’ drive from downtown which makes it one of the top romantic getaways near Chicago. It just so happens that Galena is also very LGBTQ+ friendly, allowing couples to relax while wandering the civil-war era Main Street, browsing the town’s many boutiques and art galleries before indulging in a farm-to-table feast. Of the many things to do in Galena, consider taking a tour of a microbrewery or local winery in the countryside, or enjoy the region’s best sporting opportunities; golf in summer or skiing in winter. Boasting the ‘Best Main Street in the Midwest’, Galena is sure to charm with its sunset cruises up the Mississippi River and opportunities to tie the knot while flying in a hot air balloon.

Fabulous B&Bs, world-class resorts and spas abound, with our top choices for gay travellers being Aldrich Guest House or the Inn at Irish Hollow.  Gay-owned Aldrich Guest House is just five minutes from Main Street and dates back to Lincoln’s presidency. As well as plush halls and a country feel, all guests receive free fancy toiletries, a full breakfast and refreshments (wine!) every day at 5 pm. Alternatively, the Inn at Irish Hollow owns quaint yet up-to-date cottages on a working farm which serves up fresh produce daily. The hosts at both B&Bs guarantee a good time, organising excursions such as horseback and stagecoach riding. If you have a car and some extra time, take The Great River Road which runs along the Mississippi from Galena to Southern Illinois and is said to be one of the most scenic drives in America.

Photo: Gavin Hang

Photo: Todd Trapani

2. Milwaukee, Wisconsin

Lying even closer to Boystown yet in a different state entirely, is Wisconsin’s art, music and food capital Milwaukee, a 90-minute drive from Chicago on the I-94 West highway. Milwaukee’s event calendar is buzzing with food festivals and concerts, centred on downtown, with the masterful architecture of Milwaukee Art Museum a sight for all seasons. It’s recommended to leave winter for the locals as snowfall is intensified by the city’s closeness to Lake Michigan. The answer of what to do in Milwaukee is better answered in spring, summer and fall when visitors can take advantage of the city’s great lakefront trails and parks. Notable activities to indulge in while in Milwaukee include catching a home baseball game at Miller Park, channelling your inner Hells Angel at the Harley-Davidson Museum or gracing the lavish Pabst Mansion.

The Milwaukee River runs through downtown marking the trail for a number of great city walks but spare some time to explore the outer districts such as the heritage neighbourhoods of Third Ward and Cedarburg village. If you’re looking for the gay community in Milwaukee, head to the area between downtown and Walker’s Point where the city’s gay bars congregate. Offering everything from classy martini lounges to beer-swilling dive bars, there’s a crowd for everyone.

Milwaukee | Photo: Pedro De Sousa

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Milwaukee’s event calendar is buzzing with food festivals and concerts, centred on downtown, with the masterful architecture of Milwaukee Art Museum a sight for all seasons

3. Starved Rock State Park, Illinois

For outdoorsy adventures to remember we travel to Starved Rock State Park, just under two hours’ drive from Chicago via the I-55 South and I-80 West. Not one but two parks take up over 2,600 acres extending south of the Illinois River, bursting with wildlife and hiking trails that bypass both waterfalls and canyons. Try the 4-mile trek within the Ottawa and Kaskaskia canyons, or take on Lover’s Leap before breaking out your paddleboard for a ‘Belle of the Rock’ experience on the Starved Rock Lock and Dam. Don’t dry off without considering white-water rafting or other canoe or kayak activities.

To the east, the historic town of Ottawa marks the main gateway to Starved Rock, where visitors can enjoy a bevvy or two along the waterfront after a long day of exploring. The nearby towns of Utica and LaSalle also have a similar vibe and are good places to recuperate. Starved Rock is one of Illinois’ most popular marks meaning that it can get busy at major spots. To avoid any crowds, head deeper into the adjacent Matthiessen State Park, opting to tackle the 5-mile trails which offer some incredible vantage points.

Starved Rock State Park | Photo: Yinan Chen

Photo: Max Bender

4. Saugatuck, Michigan

One of the top weekend getaways in Michigan is Saugatuck, lying just over two hours from Chicago and luring visitors from all over the Midwest with its leisurely lakeside vibes. The famous Oval Beach tipped as the best beach in the region, is your spot for boardwalk strolls along Lake Michigan, commingled with kayaking, paddle boating or sailboat cruises come sunset. Reminiscent of the Hamptons, Saugatuck offers all the R&R you might need while also sating your cultural urges. Known as the ‘art coast of the Midwest’, one of the top things to do in Saugatuck is to check out the town’s vibrant art scene. Home to dozens of art galleries, expanding into the nearby towns of Douglas and Fennville, downtown Saugatuck is a hub for both art and artsy boutiques. Creatives looking to get involved can take art classes or attend a summer fair organised by the Art Institute of Chicago’s Ox-Bow School of Art.

If art is not your forte, maybe you’ll find your happy place at the Saugatuck Brewing Company where you can attend a beer brewing event. Other ways to pass the time include taking a ‘fall colour’ tour aboard the Star of Saugatuck in Autumn or hiking in the state park. When you’re looking to get cosy, opt for one of the town’s romantic inns, B&Bs or independent hotels, a number of which are LGBTQ-owned. The open-minded community in and surrounding Saugatuck makes for a memorable gaycation packed with arts, nature and historic attractions. For more about Saugatuck’s gay credentials, visit here.

Photo: Joshua Oluwagbemiga

Photo: Sebastian Frohlich

5. Lake Geneva, Wisconsin

Our fifth and final foray into the Midwest takes us to Lake Geneva in southwest Wisconsin, one of the coolest weekend trips from Chicago, bringing inspiring views and picturesque nature right to the water’s edge. Get wet and wild with swimming and water sports, or enjoy (boozy) sailing excursions around the lake at sunset. On land, Wisconsin proffers an entire city bursting with activity – shopping, hearty cuisine and a happening bar scene – supplementing the gorgeous natural sights that surround. All within two hours of Chicago, Lake Geneva is enjoyable at any speed. Whether it’s an action-packed weekend of zip-lining and hot air ballooning or a slow-paced spa weekend, Lake Geneva brings a buzzing ambience and stunning backdrop regardless of the season. While summer is prime time for cruising, you might also consider the perks of Winterfest in January and February.

Wisconsin | Photo: Rajvinder Singh

Hand over the hard work to Mr Hudson

Our team of trip design experts at Mr Hudson are eager to help you design the perfect weekend getaway from Chicago. Whether you want ultimate relaxation or high-octane adventure, we’ll provide a full itinerary of activities based on your unique needs, wants and travel interests, as well as details on where to eat, where to party and sightseeing spots in the area. Learn more about our Trip design service here.

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