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Chicago
Travel Guide

The Windy City whips up a heady mix of basement blues, penthouse views, elevated rails and lake-front trails.

Chicago is the Windy City that loves the Blues, where gangsters like Al Capone ran rings round the Feds, and where the skyscrapers rose as the stock markets fell. A jangling metropolis, with a thicket of classy, glassy towers shooting skywards from the shores of Lake Michigan. All that is part of the draw to this, the third biggest city in the United States. But Chicago can surprise too.

While it has one of the busiest skylines of any American city – with four of the tallest buildings in the US – Chicago had the sense to build its streets wide. So its hundred high-rises don't leave you claustrophobic, unlike some other cities that reached for skies. And Chicago's love of wide open spaces can be seen when you scale its biggest skyscraper, the Willis Tower. Look east from one of its glass balconies, and you'll see the long green-and-gold strip of the Lakefront, with its parks and museums, beaches and piers.

'Chicago's Lawn' is what Chicagoans call it, and it's where they go to play. Lincoln Park is 13 kilometres of sandy beaches and park greenery, just a step or two from the city's central district, the Loop. Here you'll find the Lincoln Park Zoo, the oldest in the country, and Lincoln Park Conservatory, home to giant palms, rare orchids and some peace from Chicago's bustle. The Chicago History Museum is here too, and will set you straight on the Windy City's often blustery past.

The Navy Pier divides northern Lincoln Park from the southern stretch of Grant Park (and its radically different Millennium Park). The Pier takes you out into Lake Michigan, and a chance to mess about on the water – or to look back at Chicago's dramatic skyline from its Ferris wheel. You'll also see a line of white-pillared and glass-fronted museums stretching along the Grant Park area: the Art Institute Of Chicago, the Field Natural History Museum, the Museum of Science and Technology, and the Shedd Aquarium. They all do what they say on their entrance signs – educating and inspiring with some of the finest collections, and the most immersive exhibits, to be found anywhere in the world.

Culture and science may rule the Lakefront area, but commerce and shopping are kings in the busy streets of the central Loop – especially the Magnificent Mile. This luxury shopping street is packed with malls, restaurants and stunning architecture – and plenty of opportunities to exercise your credit card.

A more graceful architectural walk can be had in Oak Park, a western suburb where Frank Lloyd Wright lived and worked. Widely seen as America's best architect, he left the area with a treasure trove of buildings – including the Unity Temple, seen as the world's first truly modern building. Visit the Frank Lloyd Wright Home and Museum to get an in-depth guide. Oak Park also does literature – it is home to Chicago-born Ernest Hemingway, and the Ernest Hemingway Museum And House tells the remarkable story of America's foremost storyteller.

But how about rounding your Chicago stay by fusing all four at a game of baseball at Wrigley Field. After all, this iconic stadium is where the Windy City's most vital living history is played out every season.

Chicago Travel Guide Video

Where to stay in Chicago

Aloft Chicago Mag Mile
Aloft Chicago Mag Mile
3 out of 5
243 E. Ontario, Chicago, IL
The price is NZ$183 per night from 2 May to 3 May

Located in Near North Side, this hotel is within 1 mi (2 km) of Northwestern Memorial Hospital, Navy Pier and Millennium Park. Art Institute of Chicago and Willis ...

4.4/5Excellent! (1,371 reviews)

"Convenience to downtown"…"

Reviewed on 9 Apr. 2021

Aloft Chicago Mag Mile
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by Hilton
4.5 out of 5
85 East Wacker Drive, Chicago, IL
The price is NZ$282 per night from 12 Apr. to 13 Apr.

Located in The Loop, this luxury hotel is steps away from Chicago Riverwalk and Michigan Avenue. Grant Park and Chicago Theatre are also within 10 minutes. Clark-Lake ...

4.6/5Wonderful! (2,691 reviews)

"The People at the main entrance are great....."…"

Reviewed on 9 Apr. 2021

LondonHouse Chicago, Curio Collection by Hilton
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
Free cancellation
The price is NZ$248 per night from 21 Apr. to 22 Apr.

Located in The Loop, this luxury hotel is within a 5-minute walk of Chicago Riverwalk and Michigan Avenue. Grant Park and Aon Center are also within 10 minutes. ...

4.3/5Excellent! (1,858 reviews)

"Everything has to buy Even WiFi is common and free in smallest hotels But swiss hotel charges for that too That was a bit disappointing"…"

Reviewed on 10 Apr. 2021

Swissotel - Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Cimarron 1 Bedroom Cabin
Cimarron 1 Bedroom Cabin
3 out of 5
171 Hickory Bend, Hickory Hills, IL

Situated in Hickory Hills, this cabin is 2.8 mi (4.5 km) from Chicago Ridge Shopping Mall and within 6 miles (10 km) of SeatGeek Stadium and Water's Edge Golf ...

Cimarron 1 Bedroom Cabin
Sierra 1 Bedroom Cabin
Sierra 1 Bedroom Cabin
3 out of 5
695 Hickory Bend Road, Hickory Hills, IL

Situated in Hickory Hills, this cabin is 2.8 mi (4.5 km) from Chicago Ridge Shopping Mall and within 6 miles (10 km) of SeatGeek Stadium and Water's Edge Golf ...

Sierra 1 Bedroom Cabin
Pittsfield Apartments + Suites
Pittsfield Apartments + Suites
2.5 out of 5
55 E Washington St., Chicago, IL

Located in The Loop, this aparthotel is steps away from Chicago Cultural Center, Grant Park and Millennium Park. Chicago Theatre and Michigan Avenue are also ...

3.1/5 (1,265 reviews)

"I did not stay there because I was told by security management shout down the building which my family I was able too check in our room, he would not allow us to speak with any one else about the matter (ALL OVER A FACE MASK) ruined my night.. I try calling front desk no one would answer I WOULD ..."…"

Reviewed on 22 Jun. 2020

Pittsfield Apartments + Suites
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit in Chicago

Top activities in Chicago

Reviews of Chicago

4.7

Top Destination

5 - Excellent
116
5 - Excellent 74.83870967741936%
4 - Good
35
4 - Good 22.580645161290324%
3 - Okay
4
3 - Okay 2.5806451612903225%
2 - Disappointing
0
2 - Disappointing 0%
1 - Terrible
0
1 - Terrible 0%

4/5 - Good

Verified traveller

16 Feb. 2020

A great place to visit, love all difference architectures.

5/5 - Excellent

Verified traveller

1 Feb. 2020

Great architecture, and a lovely walk by the lake

5/5 - Excellent

Verified traveller

24 Jan. 2020

Great city lots to see and do

5/5 - Excellent

Verified traveller

1 Jan. 2020

Clean, well laid out city with lots great attractions and amenities. Excellent nightlife and shopping.

5/5 - Excellent

Verified traveller

27 Dec. 2019

Reminded me of New York except more relaxed and Chicago sleeps

5/5 - Excellent

Verified traveller

14 Dec. 2019

Andy's Jazz Club. Awesome night.

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