Why Go to Chicago
YOUR DESTINATION AT A GLANCE
Chicago has always grown faster than anyone could predict. Mark Twain marveled that the city outpaced every forecast made about it, and that energy still defines the Windy City today. Its story is a big one: an industrial powerhouse that dazzled the world at the 1893 World's Fair, a Prohibition-era playground for gangsters like Al Capone, and a magnet for waves of Greek, Polish, Italian, Irish, Jewish and many other immigrants who shaped its neighborhoods.
Today Chicago is one of America's great cities, with world-class art, distinct neighborhoods, fantastic shopping and an incredible food scene. Plan to spend plenty of time looking up. The Chicago Architecture River Cruise is one of the best tours in the country, and Millennium Park, home of the shiny Cloud Gate sculpture, is a must. For views from above, head to Skydeck Chicago at Willis Tower or 360 Chicago at the former John Hancock Center. Then dive into the rest: amazing museums like the Art Institute, passionate sports fans, live blues and jazz, and of course deep-dish pizza.
Chicago is easy to reach by plane or train from much of the country. I'll pick a hotel in the right neighborhood and plan your architecture, museum and food highlights.
BEST FOR
Architecture enthusiasts, foodies, museum lovers and urban explorers
BEST MONTHS
May to October
EXPLORE
The Loop has major architectural landmarks and Millennium Park; River North offers dining and galleries; Lincoln Park features green space, and Hyde Park is home to major museums.
SIX18 SIGNATURE DESTINATION GUIDE
Chicago
North America › Midwest › USA › Illinois
Soaring architecture, lakefront beaches and deep-dish pride in America's Second City.
Lake & River
Architecture
Culinary
Sports
SIX18 INSIDER TIP
Book the architecture river cruise early in your trip. It's the best introduction to the city and helps you recognize landmarks the rest of your stay.
Experiences Worth Exploring
THINGS TO DO
Visit early in the morning for photos of The Bean without the crowds.
Millennium Park
Chicago's showpiece park is home to Cloud Gate ("The Bean"), the Crown Fountain and free summer concerts at the Pritzker Pavilion.
Allow at least half a day, and don't miss the Thorne Miniature Rooms.
Art Institute of Chicago
One of the world's great art museums, home to American Gothic, Nighthawks and an incredible Impressionist collection.
Choose the Chicago Architecture Center's tour for the best guides.
Chicago Architecture River Cruise
A 90-minute boat tour along the Chicago River, with expert guides explaining the city's famous skyline.
Rent a kayak or electric boat for a fun view of the skyline.
Chicago Riverwalk
A pedestrian path along the river lined with cafés, wine bars and boat rentals.
Go on a clear day, early in the morning or near sunset.
Willis Tower Skydeck
Step out onto The Ledge, a glass box extending from the 103rd floor of the Willis Tower.
A luxury hotel just off the Magnificent Mile with a celebrated spa, a top-floor pool and exceptional service.
The Peninsula Chicago
Magnificent Mile
City
A sleek luxury hotel in a Mies van der Rohe tower overlooking the Chicago River.
The Langham, Chicago
River North / Chicago River
City
A historic former athletic club turned hotel, with a rooftop bar overlooking Millennium Park.
Chicago Athletic Association
Loop / Millennium Park
Boutique · City
A stylish hotel in the historic Art Deco Carbide & Carbon Building, near Millennium Park.
Pendry Chicago
Loop / Michigan Avenue
City · Boutique
A refined Gold Coast hotel with lake views, a spa and elegant rooms.
Four Seasons Hotel Chicago
Gold Coast
City
A design hotel in an Art Deco tower with rooftop bars.
The Robey
Wicker Park
Boutique
A boutique hotel across from Wrigley Field.
Hotel Zachary
Wrigleyville
City · Boutique
A historic Loop building turned stylish boutique hotel with a rooftop bar.
Kimpton Gray Hotel
The Loop
Boutique · City
A huge, good-value hotel on the Riverwalk, good for families.
Hyatt Regency Chicago
Riverwalk / Loop
City · Family · Value
A grand historic hotel known for its ornate lobby.
Palmer House Hilton
The Loop
City
Curated Accommodations
WHERE TO STAY
November in Chicago
High 48°F · Low 34°F · Rain 3.1 in
The Magnificent Mile Lights Festival kicks off the holiday season, and Christkindlmarket opens.
The best time to visit Chicago is May through October, when the weather is warm and the city is full of festivals. Summer is lively, while fall brings crisp air and beautiful colors. Winter is cold and windy, but the holiday season is festive.
Best Times to Visit Chicago
WHEN TO GO
Where to Dine
DINING
Chicago's food scene is world-class, from deep-dish pizza and Italian beef to Michelin-starred tasting menus.
- Classic eats: Try deep-dish pizza, an Italian beef sandwich and a Chicago-style hot dog (no ketchup!).
- Neighborhood dining: West Loop's Restaurant Row and Pilsen are full of great restaurants.
- Must-try: Deep-dish pizza, Italian beef, Chicago-style hot dogs and Garrett's popcorn.
06
Divvy Bikes
Divvy bike-share stations are found throughout the city, perfect for the Lakefront Trail.
05
Water Taxis
Water taxis on the river and lake are a scenic way to travel in summer.
04
Taxis & Rideshares
Taxis and rideshares are widely available throughout the city.
03
Buses
CTA buses cover the city, including routes along the lakefront.
02
The L
Chicago's elevated trains connect downtown with neighborhoods and both airports. Tap a contactless card or phone to ride.
01
Flying In
O'Hare (ORD) is about 45 minutes from downtown on the CTA Blue Line. Midway (MDW) is closer, about 25 minutes on the Orange Line.
Most visitors fly into O'Hare or Midway and take the L downtown. Once you're here, trains, buses and Divvy bikes make it easy to get around. Skip the car: parking downtown is expensive.
Getting Around Chicago
GETTING AROUND
KEEP EXPLORING
You Might Also Like