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Book cheap holidays to Chicago

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Map of hotels in Chicago

Recommended holiday deals

8 days / 7 nights
DepartingSat, 21 Sep 2019
HI Chicago
21 Sep 2019 - 28 Sep 2019
TripAdvisor rating 4.5
From £665 per person
Club Quarters Hotel, Central Loop
21 Sep 2019 - 28 Sep 2019
TripAdvisor rating 4.0
From £830 per person
Carlton Inn Midway
21 Sep 2019 - 28 Sep 2019
TripAdvisor rating 4.5
From £759 per person
Hotel Blake, an Ascend Hotel Collection Member
21 Sep 2019 - 28 Sep 2019
TripAdvisor rating 4.5
From £991 per person
8 days / 7 nights
DepartingSat, 12 Oct 2019
Holiday Inn Express Hotel & Suites Chicago-Midway Airport
12 Oct 2019 - 19 Oct 2019
TripAdvisor rating 4.0
From £557 per person
Skylark Motel
12 Oct 2019 - 19 Oct 2019
From £583 per person
Holiday Inn Express Midway
12 Oct 2019 - 19 Oct 2019
From £630 per person
Hampton Inn & Suites Bridgeview Chicago
12 Oct 2019 - 19 Oct 2019
From £679 per person
3 days / 2 nights
DepartingFri, 01 Nov 2019
More options for these dates
Hilton Chicago- Michigan Ave Cultural Mile
01 Nov 2019 - 03 Nov 2019
TripAdvisor rating 4.0
From £492 per person
W Chicago - City Center
01 Nov 2019 - 03 Nov 2019
TripAdvisor rating 4.0
From £437 per person
Hyatt Regency McCormick Place
01 Nov 2019 - 03 Nov 2019
TripAdvisor rating 4.0
From £487 per person
Hampton Inn Chicago-Midway Airport
01 Nov 2019 - 03 Nov 2019
TripAdvisor rating 4.5
From £421 per person
Hotel ratings in Chicago
Travelodge Chicago
From £802 per person
Very good service
TripAdvisor rating 3.0
Sep 09, 2019
Rodeway Inn Lyons
From £495 per person
Riot fest recovery
TripAdvisor rating 2.5
Sep 15, 2017
Extended Stay America Chicago - Midway
From £609 per person
Great Stay, but...
TripAdvisor rating 3.5
Aug 04, 2019
Oklahoma City, Oklahoma
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Flight and hotel Chicago

All About Chicago

Chicago is the third largest city in the United States. An urban Midwestern destination perfect for city breaks, Chicago is conveniently located right on the vast waters of Lake Michigan, one of the world's largest freshwater lakes. The city's friendly locals affectionately call Chicago 'My Kind of Town', in honour of musician Frank Sinatra's famous single.

What Should I Know Before Visiting Chicago?

Chicago is served by two airports, O'Hare and Midway. When viewing package holidays in Chicago and arranging your flight from London to Chicago, make sure you arrange the correct travel documents. British citizens are included in the USA's Visa Waiver Program, and can enter the country with a passport and current ESTA authorisation for holidays of up to 90 days. Apply for your ESTA at least 72 hours before your scheduled flight and hotel in Chicago. Chicago is on Central Standard Time (CST), six hours behind the UK, and uses US dollars as the local currency.

When Is the Best Time to Visit Chicago?

If you're eyeing temperate weather for your weekend Chicago, you'll want to plan your flight to Chicago in May, June, or September. During these three months, temperatures are typically pleasantly warm and ideal for sightseeing. At the height of summer, plan your package holidays in Chicago to include water activities ideal for hot weather. Winter brings cold temperatures—keep in mind they don't call this the 'Windy City' for nothing—and you might catch some snow.

Chicago hosts various festivals throughout the year. Music fans will want city breaks in Chicago to include June's Chicago Blues Fest, while foodies will love the Taste of Chicago in July. December's festivities bring in the Winter Wonderfest celebration, and an outdoor ice rink is set up at iconic Milennium Park. If you fancy a weekend in Chicago in March, you can capture the Luck of the Irish at the St. Patrick's Day Parade and River Dyeing, where the city's Chicago River is dyed green.

What to Do In Chicago

  • Sports: Locals are passionate about their home town teams. In spring and summer, catch a Cubs baseball game at historic Wrigley Field. The other baseball team, the White Sox, play on Chicago's South Side. The city's football team are the Bears, the hockey team is called the Blackhawks, and the basketball team are the iconic Bulls.
  • Shopping: Chicago's Magnificent Mile boasts nearly 500 of America's best shops, at every price point, on famous Michigan Avenue.
  • Lake activities: There are numerous outdoor activities on Lake Michigan, such as swimming, sailing, sunning, beach volleyball, and cycling.
  • Nightlife: Bars and clubs are all over the city, featuring live music and atmospheres for all tastes. Don't leave town without experiencing Chicago's world-famous late night improvisational comedy scene. The Second City improv troupe has been known to feature many future Saturday Night Live stars.

What Places Must I Visit In Chicago?

  • Willis Tower: Formerly the world's tallest building, you'll get a bird's eye view of several U.S. states on a clear day from the Willis Tower observatory.
  • Millennium Park: This stunning park boasts concert pavilions, multiple annual festivals, a garden, and ample green space. Get your photo at the iconic Cloud Gate, nicknamed 'The Bean'.
  • Field Museum of Natural History: This world-famous museum is home to Sue, the most intact Tyrannosaurus Rex ever discovered.
  • Navy Pier: The city's impressive pier is home to year-round attractions and shopping. During warmer months, watch regular fireworks and ride the Ferris wheel. In winter, go ice skating and visit the seasonal winter wonderland.
  • Chicago Riverwalk: Stroll around the river on the pedestrian and cycling path for stunning views of Chicago's famous architecture, or take a boat tour of the city.

What to Eat In Chicago

  • Deep dish pizza. Rich and delicious, deep dish pizza originated in Chicago, with Pizzeria Uno and Due and Giordano's being local favourites to try a slice.
  • Vienna hot dogs: Topped with relish, onions, peppers, and pickles, this is the signature local preparation for quality Vienna beef hot dogs. Try one at Portillo's, Supdawg, or any local food stand.
  • Italian beef: The owner of Al's Beef claims to be the inventor of this decadent sandwich, featuring flavourful roast beef on an Italian-style bread roll.

What Should I Bring Home From Chicago?

Don't forget to bring back great gifts and souvenirs after your flight from Manchester to Chicago! Your creative friends will love the local wares from The Museum Shop of The Art Institute of Chicago, which has beautiful wall art, accessories, and stationery. Foodies will enjoy a gift box with spices from Chicago's diverse cultural neighbourhoods. For family members and children, you can't go wrong with memorabilia from the Willis Tower, Lake Michigan, or one of Chicago's many sports teams.