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8 days / 7 nights
DepartingSat, 27 Oct 2018
Hampton Inn by Hilton Chicago-Midway Airport
Chicago
Flight + Hotel
8 days / 7 nights
27 Oct 2018 - 03 Nov 2018
TripAdvisor rating TripAdvisor Rating
824 Reviews
From £713 per person
Rodeway Inn Lyons
Lyons
Flight + Hotel
8 days / 7 nights
27 Oct 2018 - 03 Nov 2018
TripAdvisor rating TripAdvisor Rating
88 Reviews
From £535 per person
Holiday Inn Chicago Midway Airport
Chicago - IL
Flight + Hotel
8 days / 7 nights
27 Oct 2018 - 03 Nov 2018
From £774 per person
8 days / 7 nights
DepartingSat, 01 Dec 2018
Hilton Chicago- Michigan Ave Cultural Mile
Chicago
Flight + Hotel
8 days / 7 nights
01 Dec 2018 - 08 Dec 2018
TripAdvisor rating TripAdvisor Rating
5853 Reviews
From £574 per person
La Quinta Inn & Suites Chicago Downtown
Chicago - IL
Flight + Hotel
8 days / 7 nights
01 Dec 2018 - 08 Dec 2018
TripAdvisor rating TripAdvisor Rating
1432 Reviews
From £616 per person
The Blackstone, Autograph Collection
Chicago
Flight + Hotel
8 days / 7 nights
01 Dec 2018 - 08 Dec 2018
TripAdvisor rating TripAdvisor Rating
2323 Reviews
From £678 per person
8 days / 7 nights
DepartingSat, 05 Jan 2019
Travelodge by Wyndham Downtown Chicago
Chicago - IL
Flight + Hotel
8 days / 7 nights
05 Jan 2019 - 12 Jan 2019
TripAdvisor rating TripAdvisor Rating
2331 Reviews
From £905 per person
Write Inn Hotel
Oak Park
Flight + Hotel
8 days / 7 nights
05 Jan 2019 - 12 Jan 2019
TripAdvisor rating TripAdvisor Rating
189 Reviews
From £1,072 per person
Holiday Inn Downtown Chicago
Chicago - IL
Flight + Hotel
8 days / 7 nights
05 Jan 2019 - 12 Jan 2019
From £1,069 per person
Hotel ratings in Chicago
Carlton Inn Midway
Chicago
From £644 per person
Could not have had a better experience
TripAdvisor rating TripAdvisor Rating
799 Reviews
Oct 19, 2018
Chicago South Loop Hotel
Chicago
From £537 per person
Awesome
TripAdvisor rating TripAdvisor Rating
2099 Reviews
Oct 22, 2018
Club Quarters Hotel, Central Loop
Chicago
From £904 per person
First vacation in Chicago
TripAdvisor rating TripAdvisor Rating
2134 Reviews
Oct 22, 2018
Map of hotels in Chicago
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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.