Illinois may have travel restrictions in place, including self-quarantine, due to COVID-19.

Find out moreOpens in new tab or window

ChicagoUnited States of America

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

Top hotels in Chicago

The Godfrey Hotel Chicago
The Godfrey Hotel Chicago
4.5 out of 5
127 West Huron, at LaSalle, Chicago, IL
The price is NZ$123 per night from 27 Dec. to 28 Dec.

Located in River North, this luxury hotel is within a 10-minute walk of State Street, Michigan Avenue, and Northwestern Memorial Hospital. Chicago Riverwalk ...

4.3/5Excellent! (1,586 reviews)

"Love everything! The hotel was nice and staff was generous."…"

Reviewed on 24 Nov. 2020

The Godfrey Hotel Chicago
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$191 per night from 7 Dec. to 8 Dec.

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! (2,593 reviews)

"Great location. Walking distance to many Chicago sites! Beautiful river/city view from our room. Check-in and checkout were quick and can be contactless. The rooms are also very clean! Going to be staying here next time I’m in Chicago :)"…"

Reviewed on 24 Nov. 2020

LondonHouse Chicago, Curio Collection by Hilton
Eurostars Magnificent Mile, previously Dana Hotel
Eurostars Magnificent Mile, previously Dana Hotel
4 out of 5
660 North State Street, Chicago, IL
Free cancellationReserve now, pay when you stay
The price is NZ$173 per night from 13 Dec. to 14 Dec.

Located in River North, this romantic hotel is steps away from Chinese Consulate and State Street. Water Tower Place and Michigan Avenue are also within 10 minutes. ...

4.5/5Wonderful! (1,763 reviews)

"Great Hotel I would stay again any day. The room had a great view."…"

Reviewed on 29 Nov. 2020

Eurostars Magnificent Mile, previously Dana Hotel
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.

Holiday Rentals in Chicago

LEVEL Chicago – Old Town
LEVEL Chicago – Old Town
4 out of 5
1140 North Wells Street, Chicago, IL
The price is NZ$364 per night from 6 Dec. to 7 Dec.

This family-friendly Chicago aparthotel is located near the beach, within a 15-minute walk of State Street, Second City and Michigan Avenue. John Hancock Center ...

4.4/5Wonderful! (43 reviews)

"The staff was very attentive and nice the place was real clean. I Would definitely stay again and would recommend."…"

Reviewed on 23 Aug. 2020

LEVEL Chicago – Old Town
Staybridge Suites Chicago - Glenview
Staybridge Suites Chicago - Glenview
3 out of 5
2600 Lehigh Ave, Glenview, IL
The price is NZ$123 per night from 26 Dec. to 27 Dec.

Situated in Glenview, this golf aparthotel is within 1 mi (2 km) of Kohl Children's Museum, Glenview Park Golf Club and The Glen Club. Northbrook Sports Complex ...

4.4/5Excellent! (676 reviews)

"It was fine. We only stayed one night and weren't there most of the time."…"

Reviewed on 5 Oct. 2020

Staybridge Suites Chicago - Glenview
Staybridge Suites Chicago-Oakbrook Terrace
Staybridge Suites Chicago-Oakbrook Terrace
3 out of 5
200 Royce Blvd, Oakbrook Terrace, IL
The price is NZ$125 per night from 5 Dec. to 6 Dec.

Situated in the business district, this aparthotel is 2.4 mi (3.9 km) from Oakbrook Center Mall and 2.7 mi (4.3 km) from Drury Lane Theater. College of Dupage ...

4.3/5Excellent! (732 reviews)

"It was clean with plenty of room. Staff was great. Not much parking so we did end up parking on the street 2 of our 3 nights but definitely not a deal breaker-we’d go back."…"

Reviewed on 4 Sep. 2020

Staybridge Suites Chicago-Oakbrook Terrace
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.

Cities near Chicago

Other places like Chicago