Three miles north of downtown, Lakeview East offers everything one can want from a Chicago neighborhood, including local shops, plenty of restaurants and nightlife. It’s also the home of Northalsted, a 0.75-mile section of N. Halsted St. that has long been the heart of Chicago’s LGBTQ+ community. Check out our guide to all the fun to be had below.
Day 1: Learn the Legacy
Morning: Start your day at Elevate Coffee, a small but mighty coffee shop located in Northalsted. Get your morning dose of caffeine from the Milano cookie latte, or a Horchata cold brew for something stronger.
Midday: Discover the Legacy Walk, 10 pairs of 25’-high “Rainbow Pylons” on Halsted St. with bios of local, national and international LGBTQ+ heroes, including Freddie Mercury, artist Keith Haring and Leonard Bernstein. Keep an eye out for the numerous pride-themed murals and rainbow crosswalks that decorate the street.
Dinner: A neighborhood favorite since 2000, Kit Kat Lounge is the epitome of dinner and a drag show. Feast on a variety of dishes, from beer-battered cheese curds to pan-roasted salmon, as the Kit Kat Divas perform.
Nighttime: See some of Chicago’s best stand-up comedians at the Laugh Factory. There are shows nightly (and two on the weekends), some of which are devoted to themes like up-and-coming acts or Latin comics. All guests must be 18 years or older, and there is a two-item minimum.
Late Night: Unwind with a bang at Roscoe’s Tavern. A Northalsted staple for more than 35 years, Roscoe’s hosts nightly events, including Disney Musical Bingo on Wednesdays, $2 drinks on Thursdays and RuPaul’s Drag Race viewing parties every Friday.
Day 2: Find Balance
Breakfast: Fuel up before another big day at Yolk. Try one of the seasonal lattes and indulge in the banana nut bread French toast to cure your sweet tooth. Or opt for something savory with the breakfast mac & cheese.
Afternoon: Go for a post-breakfast stroll to the Peggy Notebaert Nature Museum. Visit the Butterfly Haven and see what Chicago looked like centuries ago at the Wilderness Walk.
For lunch, walk up Broadway and explore the diversity of Lakeview East’s culinary scene, like Korean wings at Crisp, dim sum at D Cuisine or a classic Chicago hot dog at Flub A Dub Chub’s. After, browse the selection of independent shops, like Unabridged Bookstore, Reckless Records and Foursided for local-themed cards and gifts .
Dinner: Check out Rollapalooza, a contemporary sushi bar. Start with the spicy garlic edamame or sashimi sampler, then go with something different, like the Crazy Philly or Kimchi Dynamite.
Drinks and Dancing: Get to Sidetrack, which hosts showtune singalongs Mondays, Fridays and Sundays, and themed parties on the other nights.
Day 3: Shopping and Spirits
Breakfast: Head to Pancake Cafe for breakfast classics here like the fluffy strawberry buttermilk pancakes and breakfast burrito. For the bold, it also offers brunch cocktails, including mimosas and bloody Marys.
Midday: Find your new favorite vintage accessory or the perfect addition to your collection of eclectic jewelry at Beatnix. Then, stroll down to Out of the Closet, a non-profit thrift store where 90 cents of every dollar helps fund HIV care. Finally, head up Belmont to check out Brown Elephant, a resale shop with clothes, home goods, accessories and more.
Dinner: Recharge at The Chicago Diner, a vegetarian and vegan restaurant that boasts of being “meat free since ‘83.” Enjoy the Radical Rueben made with corned beef-style seitan or meatless Thai chili “wings” that have earned it dozens of awards for Best Vegetarian Restaurant over the years.
Night Cap: End your Northalsted adventure with a late-night drink at Bobby Love’s, which has the friendly atmosphere you’ll want after a weekend of extravagant restaurants, shops and bars. Have your pick of music with the jukebox, or sing karaoke Fridays and the first Saturday of the month.
