Chicago, IL — Staycation Inspiration
10 Things To Do In Town
- Architecture Boat Tour
- Vibe: Scenic and informative
- Description: Cruise the Chicago River while learning the stories behind the city’s iconic skyline.
- Special Events: Twilight and fireworks cruises
- Best Time: Late spring to early fall
- Millennium Park + The Bean
- Vibe: Modern and iconic
- Description: Snap pics at Cloud Gate (“The Bean”), chill on the lawn, or catch a free outdoor concert.
- Special Events: Grant Park Music Festival
- Best Time: Summer
- Museum Campus Day
- Vibe: Intellectual and inspiring
- Description: Visit the Field Museum, Shedd Aquarium, and Adler Planetarium all in one lakeside loop.
- Special Events: Free museum days for IL residents
- Best Time: Year-round
- Chicago-style Food Crawl
- Vibe: Savory and indulgent
- Description: Devour deep dish pizza, Italian beef, hot dogs (no ketchup!), and a Garrett’s popcorn mix.
- Special Events: Chicago Gourmet food fest (September)
- Best Time: Year-round
- Art Institute of Chicago
- Vibe: World-class and reflective
- Description: Wander through masterpieces from Monet, Van Gogh, and contemporary artists alike.
- Special Events: After-hours events and free nights
- Best Time: Rainy or winter days
- Lakefront Trail Biking
- Vibe: Active and breezy
- Description: Bike or stroll 18 miles of lakeside path with skyline and beach views.
- Special Events: Bike the Drive (May)
- Best Time: Late spring through early fall
- Second City Comedy Show
- Vibe: Hilarious and iconic
- Description: Catch sketches and improv where legends like Tina Fey and Steve Carell got their start.
- Special Events: Touring casts and seasonal shows
- Best Time: Evenings, year-round
- Chicago Cultural Center
- Vibe: Artistic and free
- Description: Explore exhibitions and performances in a historic building with Tiffany glass domes.
- Special Events: Free concerts and lectures
- Best Time: Year-round
- Lincoln Park Zoo + Conservatory
- Vibe: Free and family-friendly
- Description: Wander through wildlife exhibits and lush tropical greenhouses — no entry fee needed.
- Special Events: ZooLights (Dec), Fall Fest (Oct)
- Best Time: Spring and fall
- Wrigley Field Game or Tour
- Vibe: Nostalgic and lively
- Description: Cheer on the Cubs or take a behind-the-scenes stadium tour in one of baseball’s oldest parks.
- Special Events: Summer concerts
- Best Time: Baseball season (April–September)
10 Things To Do Within 30 Miles
- Oak Park Frank Lloyd Wright Tour
- Vibe: Historic and artsy
- Description: Walk the leafy streets of Oak Park and see a concentration of Prairie-style homes.
- Special Events: Wright Plus Housewalk (May)
- Best Time: Spring and early fall
- Evanston Beach Day
- Vibe: Relaxed and college town cool
- Description: Head to Northwestern’s hometown for beach time, boutique shopping, and local eats.
- Special Events: Evanston Art & Big Fork Fest
- Best Time: Summer
- Ravinia Music Festival (Highland Park)
- Vibe: Musical and picnic-perfect
- Description: Bring a blanket and wine to this legendary open-air music venue.
- Special Events: Full summer concert lineup
- Best Time: Summer
- Chicago Botanic Garden (Glencoe)
- Vibe: Serene and colorful
- Description: Roam 385 acres of themed gardens, trails, and greenhouses.
- Special Events: Lightscape (winter), orchid show (spring)
- Best Time: Spring through fall
- Skokie North Shore Sculpture Park
- Vibe: Creative and quirky
- Description: Walk or bike a trail lined with over 60 outdoor sculptures.
- Special Events: Art in the Park weekend
- Best Time: Late spring through early fall
- Andersonville + Swedish American Museum
- Vibe: Cozy and multicultural
- Description: Explore indie shops, local food, and Nordic heritage in this beloved neighborhood.
- Special Events: Midsommarfest (June)
- Best Time: Summer
- Arlington Park Racetrack (until closure repurposed; check alt events)
- Vibe: Retro and sporty
- Description: Former horse racing site now hosts seasonal events and future developments.
- Special Events: Check local event calendar
- Best Time: TBD
- Baha’i House of Worship (Wilmette)
- Vibe: Peaceful and architectural
- Description: Marvel at this intricate white temple and reflect in the peaceful gardens.
- Special Events: Open house programs
- Best Time: Spring and summer
- Rosemont Entertainment District
- Vibe: Social and family-friendly
- Description: Ice skating, bowling, concerts, and shopping right near O’Hare.
- Special Events: Parkway Bank Park events year-round
- Best Time: Winter for lights, summer for concerts
- Brookfield Zoo
- Vibe: Animal-focused and fun
- Description: Visit large naturalistic exhibits like Tropic World and Great Bear Wilderness.
- Special Events: Holiday Magic, ZooBrew
- Best Time: Spring and early fall
10 Things To Do Within 60 Miles
- Indiana Dunes National Park
- Vibe: Outdoorsy and surprising
- Description: Hike forested dunes and relax on sandy shores just over the Indiana border.
- Special Events: Ranger-led hikes
- Best Time: Summer
- Lake Geneva, WI
- Vibe: Lakefront charm
- Description: Rent a boat, stroll the shore path, or relax at a spa resort.
- Special Events: Winterfest ice sculptures
- Best Time: Summer or fall foliage season
- Starved Rock State Park
- Vibe: Nature escape
- Description: Explore waterfalls, forest trails, and scenic canyon views.
- Special Events: Eagle Watching Weekends (January)
- Best Time: Spring and fall
- Milwaukee Day Trip
- Vibe: Chill and beer-loving
- Description: Explore the Milwaukee Public Market, visit the Harley-Davidson Museum, or sip at Lakefront Brewery.
- Special Events: Summerfest (June/July)
- Best Time: Summer
- Cantigny Park (Wheaton)
- Vibe: Educational and scenic
- Description: Tour a war museum, rose garden, and estate grounds.
- Special Events: Revolutionary War reenactments, summer concerts
- Best Time: Spring and summer
- Geneva, IL
- Vibe: Quaint and festive
- Description: Browse boutiques and bakeries in a storybook downtown.
- Special Events: Swedish Days (June)
- Best Time: Spring through fall
- Naperville Riverwalk
- Vibe: Leisurely and charming
- Description: Paddle boats, covered bridges, and cafés make this a relaxing micro-getaway.
- Special Events: Summer concerts and Ribfest
- Best Time: Summer
- Elgin + Fox River Trail Biking
- Vibe: Sporty and small-town
- Description: Enjoy riverside views and low-key bike routes.
- Special Events: Art shows and farmers markets
- Best Time: Fall
- Aurora Paramount Theatre + Outlet Mall
- Vibe: Affordable and entertaining
- Description: Shop and see Broadway-quality shows in this western suburb.
- Special Events: Musical season + Christmas Walk
- Best Time: Winter and spring
- Gurnee Mills + Six Flags Great America
- Vibe: Thrilling and commercial
- Description: Big rides and big shopping await just north of the city.
- Special Events: Fright Fest, Holiday in the Park
- Best Time: Summer or October
