Do you need help?

Call for exclusive deals: 0800 026 3696

Book cheap holidays to Chicago

Why book your Flight + Hotel with Opodo?
  • Flexibility. Travel your own way
  • Save up to 40%
  • Book quickly, easily and conveniently
Map of hotels in Chicago

Recommended holiday deals

8 days / 7 nights
DepartingSat, 13 Jul 2019
Holiday Inn O'Hare
13 Jul 2019 - 20 Jul 2019
TripAdvisor rating 3.5
From £942 per person
SpringHill Suites Chicago O'Hare by Marriott
13 Jul 2019 - 20 Jul 2019
TripAdvisor rating 4.5
From £1,060 per person
Renaissance Chicago O'Hare Suites Hotel
13 Jul 2019 - 20 Jul 2019
TripAdvisor rating 4.0
From £1,061 per person
SpringHill Suites Chicago O'Hare
13 Jul 2019 - 20 Jul 2019
From £1,070 per person
3 days / 2 nights
DepartingFri, 31 May 2019
More options for these dates
Hampton Inn by Hilton Chicago-Midway Airport
31 May 2019 - 02 Jun 2019
TripAdvisor rating 4.5
From £824 per person
Hilton Chicago
31 May 2019 - 02 Jun 2019
TripAdvisor rating 4.0
From £1,342 per person
Sleep Inn Midway Airport Bedford Park
31 May 2019 - 02 Jun 2019
TripAdvisor rating 4.0
From £645 per person
Quality Inn Midway Airport
31 May 2019 - 02 Jun 2019
TripAdvisor rating 3.5
From £636 per person
3 days / 2 nights
DepartingFri, 02 Aug 2019
More options for these dates
Hilton Garden Inn Chicago/Midway Airport
02 Aug 2019 - 04 Aug 2019
TripAdvisor rating 4.0
From £717 per person
Chicago Marriott Midway
02 Aug 2019 - 04 Aug 2019
TripAdvisor rating 4.0
From £743 per person
Courtyard by Marriott Chicago Midway Airport
02 Aug 2019 - 04 Aug 2019
TripAdvisor rating 4.0
From £727 per person
Crowne Plaza Chicago West Loop
02 Aug 2019 - 04 Aug 2019
TripAdvisor rating 4.0
From £770 per person
Hotel ratings in Chicago
Chicago South Loop Hotel
From £456 per person
Great Hotel, Comfy Beds!
TripAdvisor rating 4.0
May 16, 2019
London, United Kingdom
Club Quarters Hotel, Central Loop
From £1,171 per person
We enjoyed our stay. Very comfortable
TripAdvisor rating 4.0
May 18, 2019
Nebraska City, Nebraska
Carlton Inn Midway
From £672 per person
Great job for what it is
TripAdvisor rating 4.5
May 05, 2019
Milwaukee, Wisconsin
Destination Logo

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.