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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, 25 May 2019
Carlton Inn Midway
25 May 2019 - 01 Jun 2019
TripAdvisor rating 4.5
From £991 per person
Hampton Inn by Hilton Chicago-Midway Airport
25 May 2019 - 01 Jun 2019
TripAdvisor rating 4.5
From £1,203 per person
Travelodge by Wyndham Downtown Chicago
25 May 2019 - 01 Jun 2019
TripAdvisor rating 3.0
From £1,114 per person
Hyatt Regency McCormick Place
25 May 2019 - 01 Jun 2019
TripAdvisor rating 4.0
From £1,794 per person
8 days / 7 nights
DepartingSat, 10 Aug 2019
Hilton Chicago
10 Aug 2019 - 17 Aug 2019
TripAdvisor rating 4.0
From £1,111 per person
Best Western Grant Park Hotel
10 Aug 2019 - 17 Aug 2019
TripAdvisor rating 3.5
From £948 per person
Hilton Garden Inn Chicago/Midway Airport
10 Aug 2019 - 17 Aug 2019
TripAdvisor rating 4.0
From £972 per person
Carleton of Oak Park
10 Aug 2019 - 17 Aug 2019
TripAdvisor rating 4.0
From £956 per person
3 days / 2 nights
DepartingFri, 10 May 2019
More options for these dates
Hyatt Regency MC Cormick Place
10 May 2019 - 12 May 2019
TripAdvisor rating 4.0
From £451 per person
Hyatt Regency Chicago
10 May 2019 - 12 May 2019
TripAdvisor rating 4.0
From £473 per person
Sheraton Grand Chicago
10 May 2019 - 12 May 2019
TripAdvisor rating 4.0
From £465 per person
Palmer House a Hilton Hotel
10 May 2019 - 12 May 2019
TripAdvisor rating 4.0
From £437 per person
Hotel ratings in Chicago
Hilton Chicago- Michigan Ave Cultural Mile
From £457 per person
Spectacular customer service
TripAdvisor rating 4.0
Mar 15, 2019
Chicago South Loop Hotel
From £1,047 per person
TripAdvisor rating 4.0
Feb 16, 2019
Nashville, Tennessee
Club Quarters Hotel, Central Loop
From £1,028 per person
Great location and stay
TripAdvisor rating 4.0
Mar 17, 2019
Chicago, Illinois
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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.