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USA

Chicago and the Great Lakes Holidays

GREAT LAKES? WE’VE GOT YOU.

Stretching across eight US states and one Canadian province – holding an estimated six quadrillion gallons of water within its borders – Chicago and the Great Lakes is a region of truly epic proportions. From the pristine lakes and maple-packed forests to the quaint, shoreside towns and skyscraper-studded cities, holidays here really do ‘have it all’.

Whether you’re planning an epic road trip, a luxury getaway, or a wild adventure, there’s a high chance your holiday will begin in the captivating city of Chicago. A cultural hub full to the brim with museums, parks, jazz venues and locally loved pizza spots, there’s no better place to kick things off. Of course, it’s not the only city to see across the Great Lakes region. You can make a stopover in trendy Toronto, step into Cleveland’s rock n’ roll scene, attend a high-adrenaline ice-hockey match in Detroit, or museum-hop your way around picturesque Pittsburgh – and that’s just scratching the surface.

North America has five Great Lakes in total - Superior, Michigan, Huron, Erie, and Ontario. You could create your very own highlight reel, seeing the top sights of all the Great Lakes in one trip, or you might prefer sticking to just the one and exploring more in-depth – it’s up to you! Either way, be prepared to see some incredible scenery as you dive into a world of outdoor adventure. Kayak around towering escarpments, hike along lakeside trails, search for native wildlife, or hire a boat and enjoy a tranquil afternoon on the water.

With so much more to see and do around Chicago and the Great Lakes, you can build a trip itinerary that’s perfectly tailored to you. From American city breaks to Canadian camping trips – and everything in between – our Travel Specialists can help you plan everything. Simply get in touch online, call us, or visit one of our Travelbag Shops.

Things to do

City exploring

The Lakes

Best time to go

Things to do

You’re spoilt for choice when it comes to things to do across the Great Lakes. You might fancy kicking things off in Canada with a trip to Niagara Falls. Get up close on a thrilling boat tour or complete the Journey Behind the Falls for a totally unique experience. 

Over in Michigan, by the Canadian border, Isle Royale National Park is a good place to go if you’re a fan of outdoor adventure. Walk the trails and go looking for black bears and moose. 

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If you want to spend time discovering different towns and cities, you’re in luck with a Great Lakes holiday. 

Enjoy the slow life in car-free Mackinac Island by Lake Huron, or swing by Lake Erie and visit Cleveland’s Rock and Roll Hall of Fame.

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City exploring

We can’t talk about the Great Lakes’ cities without mentioning Chicago. Illinois’ largest city, here, you can browse avant-garde sculptures at Millennium Park, see masterpieces at The Art Institute of Chicago, or catch a concert at one of the live music venues. 

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Toronto is worth a visit, too. A trip to the top of the CN Tower is a must, catching panoramic views of the cityscape below. Then you can head back down to ground level, exploring all the quirky corners, markets, and museums this city offers. 

Other not-to-miss places include Cleveland, with its excellent theatre district and rock n’ roll scene, and Minneapolis, a go-to spot for baseball fans and architecture aficionados. 

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The Lakes

If you’re planning a holiday to this region of North America, you’ll likely want to spend some time exploring the lakes themselves. A good place to start is Lake Superior – the world’s largest freshwater lake. Here, you’ll find picturesque lighthouses, gnarly rock formations and hidden waterfalls, all waiting to be discovered. 

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Lake Michigan also has a lot going for it, and there are plenty of places to visit along the shoreline. One idea is to base yourself around Traverse City, enjoying beach days and waterfront bike rides, before making your way to Torch Lake for a day trip. 

Alternatively, you could head towards the equally beautiful Lake Huron. Rent out a kayak and explore the wonders of the water, passing hidden grottos and rocky outcrops along the way.



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Best time to go to Chicago and the Great Lakes

There’s never a bad time to visit Chicago and the Great Lakes, with every season having its own perks. One of the best times to go is autumn. During these months, you’ll catch the landscape as its most vivid, with the colourful forests of Ontario being a particular highlight.

If you go a little earlier, during summer, you’ll get super toasty temperatures, perfect for days spent chilling by the lakeshore and overnight camping trips. 

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Show Less

For hiking and city sightseeing, we’d recommend a trip in one of the spring months. But if you’re looking for something different, why not opt for a winter holiday? Hit up the region’s best ski slopes and catch all the Christmas and New Year festivities.

Show More
Show Less

Things to do

Things to do

You’re spoilt for choice when it comes to things to do across the Great Lakes. You might fancy kicking things off in Canada with a trip to Niagara Falls. Get up close on a thrilling boat tour or complete the Journey Behind the Falls for a totally unique experience. 

Over in Michigan, by the Canadian border, Isle Royale National Park is a good place to go if you’re a fan of outdoor adventure. Walk the trails and go looking for black bears and moose. 

Show More
Show Less

If you want to spend time discovering different towns and cities, you’re in luck with a Great Lakes holiday. 

Enjoy the slow life in car-free Mackinac Island by Lake Huron, or swing by Lake Erie and visit Cleveland’s Rock and Roll Hall of Fame.

Show More
Show Less

City exploring

City exploring

We can’t talk about the Great Lakes’ cities without mentioning Chicago. Illinois’ largest city, here, you can browse avant-garde sculptures at Millennium Park, see masterpieces at The Art Institute of Chicago, or catch a concert at one of the live music venues. 

Show More
Show Less

Toronto is worth a visit, too. A trip to the top of the CN Tower is a must, catching panoramic views of the cityscape below. Then you can head back down to ground level, exploring all the quirky corners, markets, and museums this city offers. 

Other not-to-miss places include Cleveland, with its excellent theatre district and rock n’ roll scene, and Minneapolis, a go-to spot for baseball fans and architecture aficionados. 

Show More
Show Less

The Lakes

The Lakes

If you’re planning a holiday to this region of North America, you’ll likely want to spend some time exploring the lakes themselves. A good place to start is Lake Superior – the world’s largest freshwater lake. Here, you’ll find picturesque lighthouses, gnarly rock formations and hidden waterfalls, all waiting to be discovered. 

Show More
Show Less

Lake Michigan also has a lot going for it, and there are plenty of places to visit along the shoreline. One idea is to base yourself around Traverse City, enjoying beach days and waterfront bike rides, before making your way to Torch Lake for a day trip. 

Alternatively, you could head towards the equally beautiful Lake Huron. Rent out a kayak and explore the wonders of the water, passing hidden grottos and rocky outcrops along the way.



Show More
Show Less

Best time to go

Best time to go to Chicago and the Great Lakes

There’s never a bad time to visit Chicago and the Great Lakes, with every season having its own perks. One of the best times to go is autumn. During these months, you’ll catch the landscape as its most vivid, with the colourful forests of Ontario being a particular highlight.

If you go a little earlier, during summer, you’ll get super toasty temperatures, perfect for days spent chilling by the lakeshore and overnight camping trips. 

Show More
Show Less

For hiking and city sightseeing, we’d recommend a trip in one of the spring months. But if you’re looking for something different, why not opt for a winter holiday? Hit up the region’s best ski slopes and catch all the Christmas and New Year festivities.

Show More
Show Less

Our top 5

Mackinac Island

Take a horse and carriage along the scenic waterfront or visit one of the fascinating heritage museums.

Our top 5

Rock & Roll Hall of Fame

See original memorabilia and learn all about the makings of your favourite musical icons, from The Rolling Stones to David Bowie and Blondie.

Our top 5

Millennium Park

Snap a picture next to the iconic Cloud Gate sculpture, or stroll around the neatly pruned gardens.

Our top 5

Isle Royale National Park

Spot moose, elk and even black bears as you follow the forested hiking trails, enjoying immaculate views of the nearby Lake Superior.

Our top 5

Lake Superior

Take a kayak over the calm water or take a scenic drive along Highway 61 – stopping off for a swim along the way.

How to do Chicago and the Great Lakes

Our experts will help you tailor-make your trip

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Knowledge

Between them, our travel specialists have years of holiday expertise.

Ease

Our tailor-made holiday 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, so your booking is completely secure.

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