Chicago city waterfront and skyline

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Chicago, USA
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Worth seeing

Millennium Park, Chicago

Millennium Park

Millennium Park adds outdoor time to a Chicago stay, with open space, views or waterfront breathing room between denser city sights.

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Art Institute of Chicago, Chicago

Art Institute of Chicago

Art Institute of Chicago gives Chicago a strong culture stop for museums, exhibitions or local collections, and works best as an indoor anchor in the day's route.

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Chicago Riverwalk, Chicago

Chicago Riverwalk

Chicago Riverwalk adds outdoor time to a Chicago stay, with open space, views or waterfront breathing room between denser city sights.

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Navy Pier, Chicago

Navy Pier

Navy Pier is a named stop in Chicago worth keeping on the route when it fits the day's transport, timing and neighborhood plan.

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Willis Tower, Chicago

Willis Tower

Willis Tower is a clear heritage marker in Chicago, best used as a fixed point when grouping nearby streets, monuments and viewpoints.

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Wrigley Field, Chicago

Wrigley Field

Wrigley Field is a named stop in Chicago worth keeping on the route when it fits the day's transport, timing and neighborhood plan.

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Stay overview

Start with City centre for the easiest first Chicago stay, then compare Old Town and Waterfront when price, nightlife, quieter evenings or transfer timing matter more than being beside every major sight.

Hotels & areas

Chicago hotel choice is mostly about repeat journeys: use City centre for sightseeing, Old Town for a different local base, and Waterfront or Airport area when views, parking, airport timing or longer stays matter.

City centre

City centre is the most practical first base in Chicago, keeping main sights, restaurants and short local transfers close.

Best for: first visits, sightseeing, restaurantsSee hotel options

Old Town

Old Town is the most practical first base in Chicago, keeping main sights, restaurants and short local transfers close.

Best for: first visits, sightseeing, restaurantsSee hotel options

Waterfront

Waterfront suits travellers who want views, evening walks and a calmer base while still keeping central Chicago reachable.

Best for: views, quieter evenings, walksSee hotel options

Airport area

Airport area works mainly for early departures, late arrivals or car pickup, not for a first Chicago sightseeing base.

Best for: early flights, late arrivals, car pickupSee hotel options
See hotel options in Chicago, USA

Flights & airports

Chicago Midway International Airport (MDW) arrival plan

  • Chicago Midway International Airport (MDW)About 11 km from the centre

    Compare airport access against hotel location, arrival time, rental car pickup, late flights and onward driving before choosing the first night base.

  • Chicago O'Hare International Airport (ORD)About 25 km from the centre

    To the centre: Blue Line train to downtown, running 24 hours a day, or taxi, about 30 min.

See hotels near the airport

Public transport

  • Trains, buses and commuter railBuses take cash in exact change; transit cards are sold at selected outlets and save needing it

Rental cars

Chicago day-trip car use

Do not rent a car for central Chicago unless parking and traffic are part of the plan; use one mainly for regional day trips.

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Travel tips

Best base

Choose City centre for a first stay because it keeps main sights, restaurants and practical local movement close.

Airport timing

Leave extra time for Chicago O'Hare, especially for early flights, late arrivals, traffic or unfamiliar transfer routes.

Local movement

Plan each day in clusters around Chicago and Chicago so transfers do not consume the best sightseeing hours.

Day trips

Keep one flexible slot for nearby routes from Chicago, checking weather, transport and opening hours before committing.

Nearby ideas

Beach · about 1 h 10 min · South Shore Line train from Millennium Station

Indiana Dunes National Park

Lake Michigan dunes you can climb, with the city skyline visible across the water on clear days.

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Heritage · about 30 min · Green Line or Metra from the Loop

Oak Park

Frank Lloyd Wright's own home and studio, plus the densest cluster of his Prairie houses anywhere.

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Park · about 45 min · Metra Union Pacific North line to Braeside

Chicago Botanic Garden

Twenty-seven gardens spread over nine islands, with a bonsai collection and a Japanese garden.

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Nature · about 1 h 15 min · car south-west on I-80

Starved Rock State Park

Eighteen sandstone canyons off the Illinois River; the waterfalls freeze into columns in January.

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City history

Army constructed Fort Dearborn, which was destroyed during the War of 1812 in the Battle of Fort Dearborn by the Potawatomi before being later rebuilt.
The Potawatomi were forcibly removed from their land after the 1833 Treaty of Chicago and sent west of the Mississippi River as part of the federal policy of Indian removal.
The City of Chicago was incorporated on Saturday, March 4, 1837, and for several decades was the world's fastest-growing city.
Chicago's first railway, Galena and Chicago Union Railroad, and the Illinois and Michigan Canal opened in 1848.
The Chicago Board of Trade (established 1848) listed the first-ever standardized "exchange-traded" forward contracts, which were called futures contracts. 1850–1874 In the 1850s, Chicago gained national political prominence as the home of Senator Stephen.
Lincoln was nominated in Chicago for U.S. president at the 1860 Republican National Convention, which was held in a purpose-built auditorium called the Wigwam.
Rauch established a plan for Chicago's park system in 1866.
On October 8, 1871, the Great Chicago Fire destroyed an area about 4 miles (6.4 km) long and 1-mile (1.6 km) wide, a large section of the city at the time.
The University of Chicago, formerly at another location, moved to the same South Side location in 1892.
In 1900, the problem of sewage contamination was largely resolved when the city completed a major engineering feat.
In 1956, the city conducted its last major expansion when it annexed the land under O'Hare airport, including a small portion of DuPage County.
Major construction projects, including the Sears Tower (now known as the Willis Tower, which in 1974 became the world's tallest building), University of Illinois at Chicago, McCormick Place, and O'Hare International Airport, were undertaken.
Du Sable was of African descent, perhaps born in the French colony of Saint-Domingue (Haiti), and he established the settlement in the 1780s.
As the site of the Chicago Portage, the city became an important transportation hub between the eastern and western United States.