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East Coast USA

Chicago holidays

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Can-do Chicago

Situated in the northern state of Illinois, on the shores of Lake Michigan, Chicago is famous for its jazz music, tasty pizza and skyline of architectural skyscrapers. But you’ll find plenty more attractions on your Chicago holiday, including the fun-filled Navy Pier, incredible eateries, and lots of beautiful parks and gardens.

Chicago holidays give you the chance to visit a cultural hub with numerous historical and scientific attractions – and it’s a fantastic choice for families. You can visit ‘Sue’ the tyrannosaurus rex at the Field Museum of Natural History, or enjoy the thrill of viewing the striking skyline from one of the city’s tallest buildings. Relax on one of the many sandy beaches by Lake Michigan, or have a fun day out at Navy Pier. Or enjoy some retail therapy at the big-name shops and independent boutiques on the Magnificent Mile, where you can quench your thirst for the perfect shopping experience. 

And no trip to Chicago would be complete without tucking into the city’s famous deep-dish pizza. This place is also world-renowned for its buzzing nightlife, and you’ll notice that sounds of blues and jazz fill the air after dark. Enjoy the ultimate night out, as you munch on tasty pizza and listen to live music. Whatever you’re into, there’s something for everyone on a Chicago holiday – speak to our Travel Specialists to plan your perfect getaway.

Things to do

Daytrips

Dining scene

Best time to go

Things to do in Chicago

You won’t be short of things to do during your holiday in Chicago. There are so many “must do's” that it’s difficult to know where to start. So why not start at the top? In the John Hancock Centre, you can lean out and admire the city skyline from TILT! at 360 Chicago.

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Back on ground level, if you fancy something a bit more chilled, go for a stroll through Millennium Park and get a photo in front of ‘The Bean’ – one of the most photographed spots in the city – or do some shopping along the Magnificent Mile. Make sure you also head to Navy Pier. One of Chicago's iconic attractions, this lakeside jetty serves up live music and rides, including a 60-metre Ferris wheel.  If you still have time to kill, why not take a Segway tour along Lake Michigan or get out on the water on a boat trip?



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Chicago daytrips

If you want to get out of the city and explore more, there are plenty of options to choose from. You could head to Six Flags Great America – about an hour’s drive from Chicago – and ride some of the 14 thrilling rollercoasters, or visit the 20-acre water park where you can spend a day splashing about, learning to surf, and floating along the lazy river.

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On the southern shores of Lake Michigan, roughly an hour’s drive from the city, you’ll find a 15-mile stretch of beach perfect for a relaxing day out. Or you could head to The Morton Arboretum. Covering a whopping 1,700 acres, this incredible display of Mother Nature reminds us all about the importance of protecting our planet for future generations to come.

When you’ve exhausted your options in The Windy City, why not take a road trip to see more of the USA? After all, Chicago is where the iconic Route 66 begins.



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Chicago dining

A visit to Chicago isn’t complete without eating their world-famous classic deep-dish pizza. It was first introduced at Pizzeria Uno, so this is the place to go and give it a try. And make sure you also grab a Chicago hotdog? It features Vienna beef loaded with relish, mustard, peppers, tomato wedges, a dill pickle spear and celery salt – all served in a steamed poppyseed bun.

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Show Less

Pizza and hotdogs aside, Chicago offers some of the best places for eating out in the USA, and some districts specialise in certain cuisines. If you’re looking for Greek food, then Devon Avenue is the place to be. Enjoy tasty noodle dishes in Chinatown, or feast on soul food and delectable barbecue delights in Chatham. Lincoln Square and Albany Park have a great range of Middle Eastern, German and Korean restaurants, while Uptown serves up a whole host of African and Asian morsels.

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Show Less

Best time to visit Chicago

Although Chicago is nicknamed ‘The Windy City’, this actually has nothing to do with the gusts that blow across Lake Michigan. It comes from the late 1800s, when politicians were deemed to be full of hot air.
Chicago holidays can be enjoyed all year round. Winter brings in lots of snow, but there’s plenty of festive cheer, including the ‘Christkindlmarket’ inspired by Germany’s seasonal markets, and the streets are decked in fairy lights. So if you fancy a spot of Christmas shopping, December is the perfect time to go.

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Show Less

But summer is the most popular time to visit Chicago. As it’s right on a lake, there’s usually a gentle breeze to take the edge off the city heat, which averages 28°C. Baseball fans could plan their trip for April, to coincide with the opening games for the Chicago Cubs, when temperatures hover in the high teens. Or why not visit in autumn? Sunny days still reach 20°C and you’ll be able to see the parks’ colourful fall foliage.

Show More
Show Less

Things to do

Things to do in Chicago

You won’t be short of things to do during your holiday in Chicago. There are so many “must do's” that it’s difficult to know where to start. So why not start at the top? In the John Hancock Centre, you can lean out and admire the city skyline from TILT! at 360 Chicago.

Show More
Show Less

Back on ground level, if you fancy something a bit more chilled, go for a stroll through Millennium Park and get a photo in front of ‘The Bean’ – one of the most photographed spots in the city – or do some shopping along the Magnificent Mile. Make sure you also head to Navy Pier. One of Chicago's iconic attractions, this lakeside jetty serves up live music and rides, including a 60-metre Ferris wheel.  If you still have time to kill, why not take a Segway tour along Lake Michigan or get out on the water on a boat trip?



Show More
Show Less

Daytrips

Chicago daytrips

If you want to get out of the city and explore more, there are plenty of options to choose from. You could head to Six Flags Great America – about an hour’s drive from Chicago – and ride some of the 14 thrilling rollercoasters, or visit the 20-acre water park where you can spend a day splashing about, learning to surf, and floating along the lazy river.

Show More
Show Less

On the southern shores of Lake Michigan, roughly an hour’s drive from the city, you’ll find a 15-mile stretch of beach perfect for a relaxing day out. Or you could head to The Morton Arboretum. Covering a whopping 1,700 acres, this incredible display of Mother Nature reminds us all about the importance of protecting our planet for future generations to come.

When you’ve exhausted your options in The Windy City, why not take a road trip to see more of the USA? After all, Chicago is where the iconic Route 66 begins.



Show More
Show Less

Dining scene

Chicago dining

A visit to Chicago isn’t complete without eating their world-famous classic deep-dish pizza. It was first introduced at Pizzeria Uno, so this is the place to go and give it a try. And make sure you also grab a Chicago hotdog? It features Vienna beef loaded with relish, mustard, peppers, tomato wedges, a dill pickle spear and celery salt – all served in a steamed poppyseed bun.

Show More
Show Less

Pizza and hotdogs aside, Chicago offers some of the best places for eating out in the USA, and some districts specialise in certain cuisines. If you’re looking for Greek food, then Devon Avenue is the place to be. Enjoy tasty noodle dishes in Chinatown, or feast on soul food and delectable barbecue delights in Chatham. Lincoln Square and Albany Park have a great range of Middle Eastern, German and Korean restaurants, while Uptown serves up a whole host of African and Asian morsels.

Show More
Show Less

Best time to go

Best time to visit Chicago

Although Chicago is nicknamed ‘The Windy City’, this actually has nothing to do with the gusts that blow across Lake Michigan. It comes from the late 1800s, when politicians were deemed to be full of hot air.
Chicago holidays can be enjoyed all year round. Winter brings in lots of snow, but there’s plenty of festive cheer, including the ‘Christkindlmarket’ inspired by Germany’s seasonal markets, and the streets are decked in fairy lights. So if you fancy a spot of Christmas shopping, December is the perfect time to go.

Show More
Show Less

But summer is the most popular time to visit Chicago. As it’s right on a lake, there’s usually a gentle breeze to take the edge off the city heat, which averages 28°C. Baseball fans could plan their trip for April, to coincide with the opening games for the Chicago Cubs, when temperatures hover in the high teens. Or why not visit in autumn? Sunny days still reach 20°C and you’ll be able to see the parks’ colourful fall foliage.

Show More
Show Less

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Ease

Our tailor-made packages make it easy for you to discover more of the world.

Value

Whether you're looking for luxury or simplicity, we've got the perfect holiday for you.

Trust

Travelbag is fully protected by ATOL and ABTA, so your booking is completely secure.

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