Chicago’s dynamic weather is often the subject of local humor, with residents joking that if one doesn’t like the current conditions, just wait fifteen minutes. This unpredictability, however, underscores a truth: Chicago consistently offers compelling reasons to embrace the outdoors.
A city that experiences all four seasons distinctly, Chicago shines in every one. Summers bring lively block parties and baseball games; fall dazzles with foliage that rivals New England’s; winter transforms Millennium Park into a skating haven; and spring revives Lake Michigan’s lakefront paths with runners and cyclists. Each season invites residents and visitors alike to venture outside and explore everything the city has to offer.
From urban parks and forest preserves to luxurious spas, climbing gyms, and exceptional food spots, Chicago is brimming with opportunities to hike, bike, swim, relax, and refuel. Here’s a curated guide to some of the best places across the Windy City to do just that.
Top Parks and Beaches in and Around Chicago
Northerly Island — 1521 S. Linn White Dr., Chicago
While Millennium Park and Grant Park attract new visitors, those who continue south past Soldier Field and turn east toward the Museum Campus discover Northerly Island. Once home to Meigs Field Airport, this now-tranquil 40-acre park offers scenic walking and biking trails that loop around a lagoon popular with migratory birds.
Steelworkers Park — 87th and Lake Shore Dr., Chicago
Located near the Indiana border, Steelworkers Park is a serene waterfront space that highlights Chicago’s effort to reclaim former industrial areas. Previously part of a U.S. Steel facility, the park features lakeside walking paths and a towering 30-foot climbing wall that once served as an ore wall.
Fort Sheridan Forest Preserve — 1275 Gilgare Ln., Lake Forest
About 45 minutes north of the city lies Fort Sheridan Forest Preserve, a former military post turned scenic haven. Visitors can hike along the 70-foot bluff for dramatic views of Lake Michigan, relax on a sandy beach, or explore over three miles of forest trails perfect for bird-watching.
Gillson Park — 800 Gillson Park Dr., Wilmette
Situated in Wilmette, Gillson Beach offers a surprisingly tropical atmosphere with its soft white sands and well-maintained amenities. Nearby, the Baháʼí House of Worship adds a tranquil visual backdrop that enhances the relaxing ambiance of the park.
Captain Daniel Wright Woods — 24830 St. Mary’s Rd., Mettawa
Especially captivating in the fall, this 750-acre preserve about 45 minutes from Chicago bursts with autumn colors from its maple and oak trees. Its three-mile trail accommodates hikers, cyclists, and horseback riders. Post-hike, visitors often head to Long Grove for the town’s famed apple cider donuts.
Relaxation and Wellness Retreats in the City
Chicago Bath House — 1914 W. Division St., Chicago
Operating since 1906 in Wicker Park, Chicago Bath House offers a traditional bathhouse experience cherished by many Eastern European locals. Guests enjoy exfoliating treatments and oak or eucalyptus branch massages, followed by hearty fare like borscht and cheese blintzes at the on-site restaurant.
Aire Ancient Baths Chicago — 800 W. Superior St., Chicago
Housed in a former paint factory, Aire is a luxurious spa that immerses visitors in a historic, candlelit atmosphere reminiscent of an ancient Roman bath. Featuring coed thermal pools and steam rooms, Aire’s most unique offering is a red wine bath experience for those seeking something truly indulgent.
First Ascent — 3516 N. Spaulding Ave., Chicago (and other locations)
Founded by local climbing enthusiasts, First Ascent has grown into a leading indoor climbing gym with six locations across Illinois. Its flagship facility in Avondale features 26,000 square feet of climbing terrain, 60-foot walls, and classes tailored to all skill levels.
Food and Drink Stops for Refueling After Outdoor Adventures
BiXi Beer — 2515 N. Milwaukee Ave., Chicago
Combining Asian-inspired cuisine with inventive house-brewed beers, BiXi Beer stands out in Chicago’s brewpub scene. Patrons can enjoy dishes like Thai Scotch eggs and Japanese milk bread sandwiches, along with dim sum brunches that feature creative items like Italian beef baos.
Hopleaf Bar — 5148 N. Clark St., Chicago
Beer aficionados from far and wide visit Hopleaf, where nearly 200 selections of domestic and international brews await. Known for its cozy ambiance and hearty Belgian-inspired dishes, including mussels and sausage platters, Hopleaf is a must-visit for serious craft beer fans.
Bungalow by Middle Brow — 2840 W. Armitage Ave., Chicago
This multi-talented spot produces its own natural wines and craft beers, bakes sourdough bread and pastries, and serves one of Chicago’s most beloved pizzas. Its versatility and high standards across the board have earned it a cult following.
Cabra —200 N. Green St., Chicago
Located on the rooftop of The Hoxton hotel, Cabra is chef Stephanie Izard’s lively Peruvian-inspired restaurant. With colorful decor, a festive atmosphere, and panoramic views of the Chicago skyline, Cabra offers an uplifting dining experience featuring ceviches, empanadas, and other vibrant dishes.
Heritage Bikes & Coffee — 2959 N. Lincoln Ave., Chicago
Half bicycle repair shop and half coffeehouse, Heritage Bikes & Coffee is the perfect pit stop for cyclists traversing the city. Guests can enjoy locally roasted coffee while browsing cycling gear or waiting for a quick tune-up.
Where to Stay: Prime Accommodations for Outdoor Enthusiasts and Urban Explorers
Hotel Lincoln — 1816 N. Clark St., Chicago
Nearly a century old, Hotel Lincoln offers charm and convenience with its prime location near Lincoln Park and the lakeshore. The hotel sits directly across from Green City Market, Chicago’s favorite farmers’ market, making it a popular choice during the warmer months. Rates start at $199.
St. Regis Hotel — 401 E. Wacker Dr., Chicago
The recently opened St. Regis Hotel delivers five-star luxury in a 101-story skyscraper designed by Jeanne Gang. With its close proximity to Millennium Park and gourmet restaurants by celebrity chef Evan Funke, the St. Regis stands out as one of Chicago’s most refined accommodations. Rates start at $550.
Nobu Hotel — 155 N. Peoria St., Chicago
This hotel, a collaboration with renowned chef Nobu Matsuhisa, blends Japanese elegance with modern comforts. Guests rave about the teak soaking tubs with sweeping city views, and the room service offerings—especially otoro sushi—provide the ultimate indulgence. Rates begin at $480.
Whether one seeks a nature retreat, a wellness day, a climbing challenge, or a memorable meal, Chicago offers something for every interest and every season. From peaceful lakeside walks to the indulgence of wine baths or Peruvian ceviche on a rooftop, the city invites both locals and travelers to immerse themselves fully in its outdoor pleasures and urban delights.
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