The Perfect Getaway: A long weekend in Chicago for Labor Day
The Windy City comes alive in the warmer months, with outdoor fests, sidewalk dining, and a bustling lakefront that’s perfect for soaking up late-summer vibes.
By Alina Dizik | July 24, 2025 (Updated October 20, 2025)
With glittering Lake Michigan reflecting off the city’s skyscrapers, Chicago goes all out once summer rolls in. Home to one of the most adventurous restaurant scenes in the country and plenty of walkable neighborhoods, the city is prime for exploring and spending time outdoors. Combine that with top museums, a long lineup of concerts, and a stunning riverfront, and you’ve got more than enough to explore for days on end. Whether you’re looking to hit the bike trail along the lakefront, kayak through downtown, or spend your days tasting your way through Chicago’s top restaurants, here’s a Labor Day weekend-inspired game plan to kick things off.
Friday
Morning
Upon arrival at the Windy City, check in at your home base for Labor Day weekend. With its beaux-arts charm, you’ll know you’re in for a treat the moment you enter LondonHouse Chicago, Curio Collection by Hilton. The 22-story glass tower, crowned with a private cupola, is the ideal spot for exploring the city’s Magnificent Mile and downtown. Spacious rooms with skyline views, a well-equipped gym, relaxing spa treatments, and standout dining options make it the ideal retreat for a memorable long weekend in Chicago.
Afternoon
Rent a kayak on the Chicago River for an up-close view of the city’s layered architectural history. Paddle past Marina City’s “corncob towers” and the Tribune Tower while you float under stunning bridges. Afterward, try a few slices from Robert's Pizza and Dough Company, which delivers on its promise to strike the ideal balance between “crunch and chew.” The Carne pizza, featuring sausage, pepperoni, and meatballs, is the perfect accompaniment to riverwalk views.
Evening
Dining meets design when you book a table at LIA (short for Life Imitates Art), a new hot spot in nearby River North. The menu focuses on shared plates served amid rotating art installations curated through their artist-in-residence program, which ties each seasonal tasting menu to a featured local artist. The result? A stylish, sensory night out, with playful standouts such as a dish called “Are You Going to Eat that Pickle?” and a mini espresso martini as part of the beverage pairing.
Saturday
Morning
Head to the residential Lincoln Park neighborhood for some classic croissants at Floriole Café & Bakery. The self-proclaimed “French-ish bakery” opened in 2010 and has been gathering crowds ever since for its delicious baked goods, seasonal specials, and cozy patio. Standouts include savory galettes, buttery croissants, sourdough loaf, and their famous quiches. Once you've had your fill, wander the neighborhood known for indie boutiques, parks, and plenty of summertime foot traffic.
Afternoon
For some much-needed R&R back at the hotel, head downstairs to the LH Spa by Windy City Massage. Traveling as a pair? Choose the 95-minute Couples Oasis, which includes a back therapy treatment and a detox foot wrap for increased circulation and stress relief. Solo guests can book massages, facials, manicures and pedicures, and body treatments to feel rejuvenated for a night on the town.
Evening
Start the night with bites at LH on 21, the hotel’s indoor lounge and restaurant, which features a classic burger sourced from nearby Slagel Farms along with American-style tapas. Afterward, head up to the top floor to enjoy the views from the stunning LH Rooftop Bar surrounded by city lights. Cocktails, including the LH Old Fashioned, Pineapple Paloma, and Purple Rain Sangria, are sure to impress. The rooftop’s historic cupola, once part of the original 1920s building, is available for private events.
Sunday
Morning
Wake up and head over to brunch at Lula Café in the Logan Square neighborhood. This farm-to-table pioneer has drawn regulars for decades with offerings like their classic breakfast burrito and trout scramble. Explore the eclectic neighborhood’s shops, breweries, and record stores along Milwaukee Avenue, or check out some of Chicago’s historic greystones along Logan Boulevard. The area is also home to a Sunday farmers' market with live music and an ever-expanding list of vendors.
Afternoon
After your morning excursion, head toward the lakefront, but not before stopping at Lincoln Park Zoo’s Nature Boardwalk for a skyline selfie. The restored Midwestern prairie habitat features walking trails and is situated at the southernmost end of the zoo. Both are free and open to the public. Then head to the 18.5-mile (29.7-km) lakefront trail to explore. Walk or bike south to check out North Avenue or Oak Street Beach, swimmable beaches with plenty of action during warmer months.
Evening
You can’t leave Chi-town without trying some Italian beef (or roast beef sandwich au jus, as it’s called elsewhere). For a modern take on the classic, look no further than the Original Wagyu Beef Dip at Gus’s Sip & Dip, a tavern that offers stellar cocktails (think a Dirty Shirley or a Mezcal Mule). Continue the night at Howl at the Moon, a longstanding piano bar that takes live song requests from the audience.
Monday
Morning
Grab some coffee and walk towards Millennium Park for a glimpse of Cloud Gate, aka The Bean. With fewer crowds on a weekday, it’s the ideal time for a closeup. Cool off with some mist from the LED-enabled Crown Fountain as you make your way to the Art Institute of Chicago, which houses one of the world’s foremost collections of Impressionist and Post-Impressionist art, with works by Monet, Van Gogh, and Cezanne.
Afternoon
Don’t leave without trying some of the city’s best tacos at Taqueria Chignon. Recently relocated to the buzzy Fulton Market District, the upscale taqueria offers chef-crafted bites inspired by Mexican street food, including the duck carnitas taco, holy mole chocolate cake, and a raclette quesadilla. Pair your meal with one of their homemade agua frescas. After lunch, wander through the West Loop for a peak into shops and art galleries, including one founded by local curator Kavi Gupta.
Until next time!
Head back to LondonHouse to grab your bags and wrap up a Labor Day weekend well spent. Whether it’s wandering through tree-lined neighborhoods, walking along the lakefront, or tracking down the tastiest bites, there’s still plenty to explore. The best part? Chicago delivers in every season.
Alina Dizik
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