Chicago Staycation Guide

Chicago, IL — Staycation Inspiration

10 Things To Do In Town

1. 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
2. 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
3. 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
4. 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
5. 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
6. 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
7. 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
8. 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
9. 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
10. 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

1. 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
2. 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
3. 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
4. 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
5. 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
6. 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
7. 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
8. 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
9. 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
10. 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

1. 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
2. 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
3. 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
4. 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
5. 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
6. 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
7. 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
8. 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
9. 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
10. 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