Illinois, United StatesThe Windy City

Chicago

Chicago puts a big skyline, a long lakefront path and some of the country's most serious food on one flat grid. It is easy to enjoy on foot and by train, and it is a natural hub for a longer trip.

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Best months: May to Oct
Ideal stay: 3 to 4 days
Train: Not confirmed
Bus: Not confirmed

Photo by Jeff Brown on Unsplash

Best months

January
February
March
April
May, a good time to go
June, a good time to go
July, a good time to go
August, a good time to go
September, a good time to go
October, a good time to go
November
December

Known as

Big city
Food city
Arts city
Music city
Lake town
Historic

Getting there

Highway / road trip
Commercial airport
Local public transit

Train and bus

Train: Not confirmed
Bus: Not confirmed

People

2,746,388

in the city, 9,434,123 in the metro area

Languages

English

Chicago sits on the southwest shore of Lake Michigan, and the lake shapes how the city feels. A path follows the water for miles, the skyline stands right behind it, and the street grid makes everything simple to read. The tall buildings of the Loop are the reason architecture fans come, but the city is just as much about its neighborhoods. Each one has its own taverns, bakeries, corner parks and local pride. Winters are hard and summers are lively, with people outside on every patio and beach. The city is large, yet it never feels hard to figure out, which makes it a comfortable stop for first-time visitors.

Start downtown. Millennium Park has the mirrored Cloud Gate sculpture, known as the Bean, and the Art Institute of Chicago sits across the street. The Chicago Riverwalk is a good place to watch the bridges, and architecture boat tours leave from the river. Willis Tower has a glass-floored observation deck. Along the lakefront, Navy Pier is the tourist draw, while the Field Museum, Shedd Aquarium and Adler Planetarium share the Museum Campus. The Museum of Science and Industry is in Hyde Park. Baseball fans can see a game at Wrigley Field, and Lincoln Park Zoo sits beside the lakefront.

Eating is the main event for many visitors. Try deep-dish pizza at least once, then move on to an Italian beef sandwich, a Chicago-style hot dog with no ketchup, and a tavern-style thin crust cut in squares. Pilsen is the place for Mexican bakeries and taquerias, and the West Loop is packed with chef-driven restaurants. For drinks, neighborhood bars are the norm. Chicago is also a blues and jazz city, and clubs such as Buddy Guy's Legends and Kingston Mines keep the music going late. Comedy fans can line up for improv in Old Town.

The Loop and River North put you near the main sights, the train stations and the river. Lincoln Park and Lakeview are calmer and have more residential streets, with the zoo and lakefront close by. Wicker Park and Bucktown suit travelers who want coffee shops, record stores and a younger crowd. The L train and buses cover most of what you need, and Metra commuter trains reach the suburbs. Driving downtown is slow and parking costs a lot, so leave the car at the hotel or in the outer neighborhoods if you can.

Late spring through early autumn is the easy season, when the lakefront is full and festivals fill the parks. June and September are especially comfortable. July and August can be hot and humid. Winter brings cold winds off the lake, but the museums, theatres and restaurants stay busy, and hotel rooms are easier to find. Give Chicago three or four days if you want to see the museums, walk a couple of neighborhoods and eat well. A long weekend covers the highlights, but you will want to add a day if you plan to see a ball game.

Chicago is the main rail hub of the middle of the country. Union Station sends Amtrak trains west on the Empire Builder and California Zephyr, south toward New Orleans and east toward New York and Boston. By road, it is where the interstates from every direction meet, and the old Route 66 starts downtown near Grant Park. Milwaukee is an easy trip to the north, the Indiana Dunes lie to the southeast, and Detroit, St. Louis and Minneapolis are each a long day's drive or an overnight train away. Many travelers use Chicago as the place to switch from one route to another.

Highlights

Millennium Park
Home to Cloud Gate, the Crown Fountain and summer concerts.
Art Institute of Chicago
A large art museum with a famous Impressionist collection, right on Michigan Avenue.
Chicago Riverwalk
A path along the river with views of the bridges and the skyline.
Architecture boat tour
A river cruise that explains the tall buildings of the Loop from the water.
Lakefront Trail
A paved path for walking and cycling along the lake and past the beaches.
Wrigley Field
A classic ballpark in Wrigleyville where the Cubs play.
Field Museum
A natural history museum on the Museum Campus.
Pilsen murals
Colourful street art and Mexican food along 18th Street.

Neighborhoods

The Loop
The downtown core, with the elevated train tracks, Millennium Park, the Art Institute and many early skyscrapers.
River North
Galleries, big restaurants and hotels packed in just north of the river.
Wicker Park
A creative area with independent shops, bars, music venues and the busy corner of Milwaukee, Damen and North.
Pilsen
A Mexican-American neighborhood known for murals, bakeries and art studios.
Lincoln Park
A leafy residential area with the zoo, the conservatory and long stretches of lakefront.
Hyde Park
A university neighborhood on the South Side with the Museum of Science and Industry nearby.

Getting around

The L trains and buses reach most places, and the Loop and the lakefront are easy on foot. Rideshare and taxis fill the gaps, and Divvy bikes help along the lakefront.

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Chicago, Illinois: travel guide | Route By Design

Best months

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Getting there

Train and bus

People

Languages

Highlights

Neighborhoods

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Scores

Where to stay

Things to do

Food & dining

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Where to next from Chicago

Best months

Known as

Getting there

Train and bus

People

Languages

Highlights

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Getting around

Scores

Where to stay

Things to do

Food & dining

In an emergency, call 911

How safe is Chicago?

Safety score

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Areas to be careful in

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Where to next from Chicago

Community

When to go

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Routes through Chicago

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Review Chicago

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In an emergency, call 911

How safe is Chicago?

Safety score

Violent crime

Areas to be careful in

Police

Hospitals