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Same sex couple walking down Lake Mil Park.

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.

Day 1:


  • Pride family walking down the streets of Chicago during summer.

Start your trip in Northalsted, Chicago’s Proudest Neighborhood, and also the first officially recognized gay village in the United States. Start with the Legacy Walk, the only outdoor LGBTQIA+ Museum in the world, which celebrates important queer contributions to world history and culture. Pick up lunch at Ann Sather’s and do not skip the cinnamon roll! Make your way just north to the Andersonville Galleria to shop and check out work from some of Chicago’s most interesting artisans. End the evening with drinks at Sidetrack’s heated outdoor patio, and then get some well deserved rest at the Best 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 by KOVAL Distillery for 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 the Baton Show Lounge, a legendary Chicago location for over 50 years that features food, fun and drag shows.

Day 2:


  • Busy shoppers on the streets of 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.

Day 3:

Oak Park

  • Exterior of a house in 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. Continue your day shopping at Rare Bird Preserves, not only do they make their tasty jams and jellies on site but you can also explore their homeware and gifts. 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.

Day 4:


  • Bakehouse owners in front their Bakery in Galena.

Begin your day in Galena exploring the unique shops along the iconic Main Street. Make sure to stop at Blaum Brothers Distilling for a tour and tasting. If wine is more your speed, take an electric bike to one of Galena’s vineyards and enjoy the scenery. 

You can’t leave Galena without embarking on a hot 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 to Durty 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 tour of Galena. For dinner, check out the patio Fritz & 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 at Miss Kitty’s Grape Escape and make sure to order one of their signature martinis.

Galena is known for their quaint accommodations. The Aldrich Guest House has been rated Galena’s number one bed and breakfast and is known for its elegance and luxury. Old World charm meets modern amenities at the Inn at Irish Hollow where you can wake up to views of rolling hills and freshly prepared cuisine. The Jail Hill Inn overlooks 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.

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