Illinois welcomes LGBTQIA+ travelers with sights, spirit and culture.
Stroll down Northalsted’s Legacy Walk, the only outdoor queer history exhibit in the world. Support a LGBTQIA+ friendly business. Then head outside Chicago to explore the vibrant charm of Galena, one of Illinois’ many welcoming cities. Ride a hot air balloon or book a quaint B&B like Jail Hill Inn – ranked #1 in the U.S. and #2 in the world by Tripadvisor in 2019.
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Day 1:
Chicago
Start your trip inNorthalsted, Chicago’s Proudest Neighborhood, and also the first officially recognized gay village in the United States. Start with theLegacy Walk, the only outdoor LGBTQIA+ Museum in the world, which celebrates important queer contributions to world history and culture. Pick up lunch atAnn Sather’sand do not skip the cinnamon roll! Make your way just north to the Andersonville Galleriato shop and check out work from some of Chicago’s most interesting artisans. End the evening with drinks atSidetrack’s heated outdoor patio, and then get some well deserved rest at theBest Western Plus Hawthorne Terrace Hotel.
There is no better way to begin a day than with brunch.D.S. Tequila Co.offers a boozy brunch with fresh Mexican and American fare on their patio. Afterward, stop byKOVAL Distilleryfor a tour and tasting of their locally famous whiskey and gin. In the summer, head down to Hollywood Beach to soak up the sun. Pro Tip: the south side of the beach is the fun side. Treat yourself to an outdoor dinner and show at theBaton Show Lounge, a legendary Chicago location for over 50 years that features food, fun and drag shows.
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Day 2:
Chicago
Head south to Chicago’s downtown for a full day of fun. Spend the morning strolling the Chicago Riverwalk and shopping on the famous Magnificent Mile. On the weekends, head over to the West Loop neighborhood to grab lunch at The Publican for modern food in a hip setting. In the afternoon, explore the Art Institute’s Modern Wing or take an architecture tour cruise on the river. Confirm openings and availability before visiting. There are so many great hotels for you to stay downtown. The Peninsula is right off of the Mag Mile and offers a 5-star luxury experience. The Kimpton Gray Hotel is one of the Loop’s newest hotels and offers modern finishes. Virgin Hotels Chicago is located right near the famous Chicago Theatre and is one of the City’s best boutique hotels.
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Day 3:
Oak Park
On your way out of Chicago, make sure to spend some time in Oak Park, one of Chicago’s most historic and charming suburbs that sits just outside of city limits. Make sure to visit the Frank Lloyd Wright Home & Studio. Of all the Oak Park homes designed by Wright, perhaps the most important is the one he made for himself. Make another Wright stop at the Unity Temple and marvel at its beauty. Grab lunch outdoors at FatDuck Tavern & Grill and make sure to order some duck fat fries. Stop by the nearby town of Riverside to check out Higgins Glass, which makes one-of-a-kind handmade glass pieces. Order a fine-dining dinner to-go at The Little Gem Cafe. If you want to stay the night, the Harvey House B&B is close to everything Oak Park has to offer.
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Day 4:
Galena
Begin your day in Galena exploring the unique shops along the iconicMain Street. Make sure to stop atBlaum Brothers Distillingfor a tour and tasting. If wine is more your speed, take an electric bike toone of Galena’s vineyardsand enjoy the scenery.
You can’t leave Galena without embarking on ahot air balloon ride. Drift above the rolling landscapes of Jo Daviess county and the historic Galena countryside while taking in stunning views from your 3,000-foot-high perch. Confirm availability before arriving. Once you’re back on solid ground, head toDurty Gurt’s for lunch to-go, and be sure to order one of their creative burgers. Afterward,hop on a trolley for a historic guided tourof Galena. For dinner, check out the patioFritz & Frites Bistro, a cozy restaurant serving European-style fare, or indulge in a steak dinner on the patio at Fried Green Tomatoes, located in a historic building with vintage character. Stop for a nightcap atMiss Kitty’s Grape Escapeand make sure to order one of their signature martinis.
Galena is known for their quaint accommodations. TheAldrich Guest Househas been rated Galena’s number one bed and breakfast and is known for its elegance and luxury. Old World charm meets modern amenities at theInn at Irish Hollowwhere you can wake up to views of rolling hills and freshly prepared cuisine.The Jail Hill Innoverlooks downtown Galena and offers gracious lodging for the perfect getaway – in 2019 the Inn was ranked the number 1 B&B in the US and the number 2 in the world. Last, but certainly not least, is the Goldmoor Inn, a B&B that offers beautiful views of the Mississippi River and whirlpool suites with private fireplaces.
Feeling peckish? Score some sweets at the LGBTQIA-owned Galena Bakehouse and get a much-needed caffeine and sugar boost.
Start Exploring
Proud to be Proud
Proud to be Proud
Arts, Culture & History
4 Days 171 Miles
Chicago, Oak Park, Galena
Embrace Illinois’ vibrant LGBTQIA+ community
Illinois welcomes LGBTQIA+ travelers with sights, spirit and culture.
Stroll down Northalsted’s Legacy Walk, the only outdoor queer history exhibit in the world. Support a LGBTQIA+ friendly business. Then head outside Chicago to explore the vibrant charm of Galena, one of Illinois’ many welcoming cities. Ride a hot air balloon or book a quaint B&B like Jail Hill Inn – ranked #1 in the U.S. and #2 in the world by Tripadvisor in 2019.
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