Visit Chicago & The Great Lakes

Chicago is a city that blends culture, architecture and a warm Midwest welcome. Wander the Magnificent Mile, catch your reflection in The Bean, admire world-class art at the Art Institute or hop on an architectural boat tour along the Chicago River. There’s live blues on most nights, deep-dish pizza on every corner and the spectacular Lake Michigan shoreline that feels more like a seaside resort than a city waterfront.

Once you’ve soaked up the buzz of Chicago, the wider Great Lakes Region opens up an entirely different side of America. A road trip here means quiet coastal drives, historic lighthouses, forest-lined highways and small lakeside towns filled with independent shops and local breweries. Whether you head into Michigan for sandy beaches, cross into Wisconsin for rolling farmland and pretty harbour towns, or venture towards Minnesota’s dramatic North Shore, the journeys are relaxed and the scenery constantly changing.

Discover holidays to Chicago and the Great Lakes Region below or speak to one of FREEDOM’s USA travel experts to create the perfect holiday for you.

Travel Guide to Chicago & The Great Lakes

Known for its striking architecture, deep-dish pizza and lakeside setting, Chicago is a great destination for a city break, as well as a starting point for exploring the Great Lakes and Route 66.

Popular things to do in Chicago

Chicago is packed with world-class attractions. Stroll the Magnificent Mile, admire your reflection in Cloud Gate (The Bean), explore the Art Institute of Chicago, or take a famous architecture river cruise. Millennium Park, Navy Pier, live blues clubs and a gorgeous Lake Michigan shoreline add to the city’s charm.

Is Chicago a good starting point for exploring The Great Lakes?

Chicago sits on the southwest corner of Lake Michigan, making it an ideal launchpad for road trips into Michigan, Wisconsin and Indiana. Within a few hours’ drive you’ll find sandy beaches, lighthouse trails, scenic coastal highways and small towns perfect for leisurely exploring.

When is the best time to visit Chicago and the Great Lakes?

Whilst summer brings sunshine and lively waterfronts in Chicago, this is the peak time to visit, so expect crowds at the most popular attractions. With winter temperatures plummeting it is not the best time for a road trip, so either late Spring or early Autumn would be perfect for either a Chicago city break, or for exploring the Great Lakes region.

How long should I spend in Chicago and the Great Lakes?

We would recommend around three to four days for a Chicago city break, or a city stay before travelling further. If you are going to explore the Great Lakes region as well, then an additional week will allow for circumnavigating most of the lakes, or longer if you wish to visit Niagara Falls as well. If you are going on to drive Route 66 then we would suggest allowing between two and three weeks to complete the journey from Chicago.

Is Chicago the starting point for Route 66?

Although it is possible to follow the Historic Route 66 in either direction, downtown Chicago marks the official beginning of the ‘Mother Road’. From Chicago you can follow Route 66 through small Midwest Towns, across the plains, through the Canyonlands and on to the Pacific Ocean, where Santa Monica Pier now marks the end of the road. Along the way you will be able to stop at classic American diners, automotive museums and various displays of oddities and Americana.

How do you plan a holiday to Chicago and the Great Lakes?

The simplest way to plan and book your holiday to Chicago and the Great Lakes, is to contact one of FREEDOM’s USA Travel Experts and discuss your plans. They can create a bespoke travel itinerary just for you. They can advise on the differences between road trips, motorhome hire, rail journeys and cross-country itineraries.