Chicago
The Windy City: Bold architecture, deep culture, deeper pizza
Chicago Neighborhoods
Each with its own character and charm
The Loop
Downtown business district
Must See:
- • Millennium Park
- • Art Institute
- • Chicago Theatre
Eat Here:
Girl & the Goat (reservations essential)
Stay if: Central for attractions
River North
Galleries and nightlife
Must See:
- • Gallery District
- • Chicago Riverwalk
- • Merchandise Mart
Eat Here:
RPM Italian
Stay if: Upscale, walkable
Wicker Park/Bucktown
Hipster haven
Must See:
- • Vintage shops
- • Music venues
- • Street art
Eat Here:
Big Star (tacos & whiskey)
Stay if: Young, artsy crowd
Lincoln Park
Family-friendly, green
Must See:
- • Lincoln Park Zoo (free)
- • North Avenue Beach
- • Chicago History Museum
Eat Here:
Alinea (3-Michelin stars)
Stay if: Quiet, residential
Wrigleyville
Sports central
Must See:
- • Wrigley Field
- • Sports bars
- • Gallagher Way
Eat Here:
Byron's Hot Dogs
Stay if: Lively on game days
Chinatown
Cultural enclave
Must See:
- • Chinatown Gate
- • Ping Tom Park
- • Chinese-American Museum
Eat Here:
MingHin Cuisine (dim sum)
Stay if: Budget-friendly
Can't-Miss Attractions
Chicago's iconic experiences
Art Institute of Chicago
MuseumImpressionist collection, American Gothic
Admission
$32 adults, $26 IL residents
Best Time
Weekday mornings
Tip: Free for IL residents on Wednesdays
Willis Tower Skydeck
Observation DeckThe Ledge glass boxes
Admission
$35-49
Best Time
Clear days, sunset
Tip: Buy tickets online to skip lines
Cloud Gate (The Bean)
Public ArtReflections of skyline
Admission
Free
Best Time
Early morning for photos
Tip: Winter creates unique ice formations
Architecture Boat Tour
Tour40+ buildings in 90 minutes
Admission
$42-47
Best Time
May-October
Tip: Chicago Architecture Foundation tours are best
Navy Pier
EntertainmentCentennial Wheel views
Admission
Free (attractions extra)
Best Time
Summer evenings
Tip: Wednesday & Saturday fireworks in summer
Chicago Food Essentials
More than just deep dish
Deep Dish Pizza
Lou Malnati's
Butter crust
45 min cook time
Pequod's
Caramelized crust
Less touristy
Art of Pizza
By the slice option
Quick service
Chicago Hot Dogs
Portillo's
Also Italian beef
Chicago chain
Gene & Jude's
No ketchup allowed
Cash only
Superdawg
Drive-in experience
Since 1948
Fine Dining
Alinea
3 Michelin stars
Book months ahead
Oriole
2 Michelin stars
Intimate setting
Gibsons Bar & Steakhouse
Rush Street classic
Power dining
Breakfast/Brunch
Lou Mitchell's
Since 1923
Free donut holes
Ann Sather
Cinnamon rolls
Swedish-American
Lula Cafe
Farm-to-table
Logan Square gem
World-Class Museums
Rain or shine entertainment
Field Museum
Natural History
Must See: SUE the T. Rex
Admission: $31-40
Time Needed: 3-4 hours
Museum of Science & Industry
Interactive Science
Must See: U-505 Submarine
Admission: $21.95-36.95
Time Needed: Full day
Chicago History Museum
City History
Must See: Chicago Fire exhibit
Admission: $19
Time Needed: 2-3 hours
Museum of Contemporary Art
Modern Art
Must See: Free Tuesdays for IL residents
Admission: $15
Time Needed: 2 hours
Getting Around Chicago
One of America's best transit systems
CTA "L" Train
Cost: $2.50 per ride, $5 from airport
Coverage: Excellent - covers most attractions
Tip: Buy Ventra card or use app
CTA Bus
Cost: $2.25 per ride
Coverage: Fills gaps between L stations
Tip: #146 or #147 for Michigan Ave
Divvy Bikes
Cost: $15/day unlimited 3-hr rides
Coverage: Lakefront Trail is amazing
Tip: Dock every 30 min to avoid fees
Taxi/Uber/Lyft
Cost: $8-25 most rides
Coverage: Everywhere, plentiful
Tip: Surge pricing during events
Water Taxi
Cost: $6 one-way
Coverage: River and lakefront routes
Tip: Scenic but seasonal
Chicago by Season
Spring (Apr-May)
Weather: 45-65°F
Highlights: St. Patrick's Day (river dyed green), Baseball season starts
Pack: Layers, rain jacket
Insider: Best weather, fewer crowds
Summer (Jun-Aug)
Weather: 70-85°F
Highlights: Beach season, festivals every weekend, outdoor dining
Pack: Sunscreen, comfortable walking shoes
Insider: Book hotels early, very busy
Fall (Sep-Nov)
Weather: 40-70°F
Highlights: Perfect weather, Marathon, architecture open houses
Pack: Light jacket, layers
Insider: Best time to visit overall
Winter (Dec-Mar)
Weather: 20-40°F
Highlights: Christmas lights, indoor attractions, restaurant week
Pack: Heavy coat, boots, gloves
Insider: Hotels cheapest, polar vortex possible
Day Trips from Chicago
Explore beyond the city
Milwaukee
Distance: 90 miles
Highlights: Breweries, Harley Museum, lakefront
Transport: Amtrak Hiawatha $25
Starved Rock
Distance: 100 miles
Highlights: Canyons, waterfalls, hiking
Transport: Car needed
Indiana Dunes
Distance: 50 miles
Highlights: Beaches, dunes, hiking
Transport: South Shore Line train
Six Flags Great America
Distance: 45 miles
Highlights: Roller coasters, water park
Transport: Car needed
Annual Events
Something happening every month
March
St. Patrick's Day Parade & River Dyeing
May
Chicago Blues Festival
June
Pride Parade
July
Taste of Chicago
August
Lollapalooza, Air & Water Show
October
Chicago Marathon, Architecture Open House
December
Christkindlmarket
Chicago Insider Tips
Local Secrets
- ✓ Lower Wacker Drive is a hidden underground road
- ✓ Free concerts at Millennium Park in summer
- ✓ Chicago Riverwalk is better than Navy Pier
- ✓ Tavern-style thin crust is what locals eat
- ✓ Green Mill for authentic jazz experience
- ✓ Architecture Biennial (odd years) is amazing
Avoid These Mistakes
- ✗ Don't put ketchup on hot dogs
- ✗ Don't call it "Willis Tower" to locals (it's Sears)
- ✗ Don't drive if you can take the L
- ✗ Don't skip the architecture tour
- ✗ Don't underestimate winter cold
- ✗ Don't miss the lakefront in summer
Experience Chicago
From architectural marvels to culinary delights, Chicago never disappoints