Chicago, on Lake Michigan in Illinois, is among the largest cities in the U.S. Famed for its bold architecture, it has a skyline punctuated by skyscrapers such as the iconic John Hancock Center, 1,451-ft. Willis Tower (formerly the Sears Tower) and the neo-Gothic Tribune Tower. The city is also renowned for its museums, including the Art Institute of Chicago with its noted Impressionist and Post-Impressionist works. ― Google
Late Spring (May–June): Ideal weather, blooming parks, and start of festival season.
Early Fall (September–October): Crisp air, fewer tourists, and gorgeous lake views.
Summer (July–August): Great for beaches and events, but can be hot and crowded.
Winter (December–February): Beautiful holiday lights but very cold; best for indoor activities and fewer crowds.
✅ Avoid late January–early March unless you're ready for frigid temps.
By Air:
O’Hare International Airport (ORD): Major hub; ~45 mins from downtown.
Midway Airport (MDW): Smaller, easier to navigate, ~25 mins from downtown.
From Airport to City:
“L” Trains:
Blue Line from O’Hare
Orange Line from Midway
By Train:
Amtrak to Union Station – From major U.S. cities like St. Louis, Milwaukee, or New York.
By Car/Bus:
Megabus, Greyhound, FlixBus run routes from nearby cities.
Millennium Park & Cloud Gate (The Bean) – Iconic photo op and outdoor events.
Art Institute of Chicago – World-famous collection, including Monet, Van Gogh, and Grant Wood’s American Gothic.
Skydeck Chicago at Willis (Sears) Tower – Glass ledge view from 1,353 ft up.
Navy Pier – Rides, shops, food, and fireworks on the lake.
Chicago Riverwalk – Scenic walking path with bars and boat tours.
Museum Campus – Includes:
Shedd Aquarium
Field Museum (home of Sue the T-Rex)
Adler Planetarium
360 Chicago (John Hancock Building) – Views of the skyline and Lake Michigan.
Lincoln Park Zoo – Free, family-friendly, near the lakefront.
Wrigley Field – Historic baseball stadium, home of the Cubs.
Chicago Architecture Center & River Cruise – Learn the story behind the skyline.
Architecture River Cruise – A must-do; fun and informative.
Stroll the Magnificent Mile – Upscale shopping and dining.
Bike along Lakefront Trail – 18 miles of scenic shoreline.
Catch a show – Broadway in Chicago, Second City Comedy Club, or a jazz/blues club.
Go to the Beach – Yes, Chicago has real beaches! Try Oak Street or North Avenue Beach.
Visit a speakeasy or rooftop bar – Try The Violet Hour or Cindy’s Rooftop.
Seasonal fun:
Summer: Lollapalooza, Taste of Chicago, baseball games.
Winter: Christkindlmarket, Millennium Park ice skating.
Luxury:
The Peninsula Chicago – 5-star with spa and rooftop pool.
The Langham – Elegant, on the river.
Four Seasons – Stunning lake views and exceptional service.
Mid-range:
The Godfrey Hotel – Trendy, with a rooftop bar.
Hotel Lincoln – Near Lincoln Park Zoo.
Kinzie Hotel – Centrally located near River North.
Budget-Friendly:
Freehand Chicago – Boutique hostel with private options.
HI Chicago Hostel – Great downtown location, clean and social.
Best Areas to Stay:
River North / The Loop: Close to attractions.
Magnificent Mile: Shopping and skyline views.
Wicker Park / Logan Square: Trendy, local vibe.
Chicago Must-Eats:
Deep Dish Pizza – Giordano’s, Lou Malnati’s, or Pequod’s.
Chicago-Style Hot Dog – All-beef dog with “everything,” no ketchup.
Italian Beef Sandwich – Portillo’s, Al’s Beef, or Mr. Beef.
Garrett Popcorn – Chicago Mix (cheese + caramel).
Tacos & Latin Eats – Try Antique Taco or Mi Tocaya.
Top Restaurants:
Alinea – Michelin 3-star, innovative fine dining.
Girl & the Goat – Small plates by Top Chef winner.
Au Cheval – Legendary burgers.
RPM Italian – Celebrity-owned, sleek setting.
Parachute – Korean-American in Avondale.
Virtue – Southern cuisine in Hyde Park.
🎶 Music Roots: Birthplace of modern blues and house music. Catch live sets in small clubs and dive bars.
🏀 Sports City: Passionate fans—Bulls (NBA), Cubs/White Sox (MLB), Bears (NFL), Blackhawks (NHL).
🎭 Comedy Scene: The Second City launched comedians like Tina Fey and Stephen Colbert.
🎨 Art & Architecture: The skyline is a museum in itself. Street murals and installations are everywhere.
🌍 Diverse Neighborhoods: Greektown, Chinatown, Little Italy, Pilsen (Mexican-American culture), and Devon Avenue (South Asian corridor).