Chicago to Michigan
Road Trip Tritinerary

The L is the superior way to get a real feel for Chicago—and it’ll only set you back US$5 a day. Short for ‘elevated’ (though some lines go underground), Chicago’s easy-to-navigate train network can take you virtually anywhere, while offering some of the best views for urban explorers. The Orange Line takes you right from Midway International Airport to the city’s most iconic downtown landmarks. You can even book a dedicated train tour to get truly acquainted. When you’re done discovering by train, rent a Divvy bike for a cycling escapade along the 18-mile Lakefront Trail, or join a group bike tour.

For adventure further afield, you can’t beat Starved Rock State Park, 90 minutes from the city. Trails wind through 18 canyons with captivating rock formations and waterfalls. If you’re keen on hiking, boating, horseback riding or simply relaxing in stunning surrounds, there’s nothing like it.

Neighboring state Michigan is also a bonanza for adventure lovers. Thanks to its northern position and low light pollution, parts of Michigan are prime positions to view the aurora borealis (northern lights). For day-time pursuits, the state is famous for its freshwater fishing (it borders four of the five Great Lakes) and is known for its quality forests, both of which provide ample adventure opportunities.

Deep dish pizza is Chicago’s culinary gift to the world: a thick cake-like crust heaped with an inverted layer of toppings—sauce goes on top of the cheese to stop it burning. If you fancy a slice of history, Pizzeria Uno invented deep dish and still operates from its original Downtown location. Other lauded local favorites are Lou Malnati’s, (60 Chicago restaurants) and Pequod’s.

Deep dish might get the glory, but it would be a mistake to visit Chicago without indulging in its other noteworthy culinary invention: Italian beef. The dish features a bun, piled with thin slices of slow-roasted beef, swimming in rich jus, and topped with giardiniera (pickled vegetables). Fans of TV show The Bear will know all about it, but nobody does it better than Johnnie’s Beef, about 20 minutes from Downtown.

Rounding out the trio of legendary local dishes: the Chicago-style hotdog is a beef frankfurter in a poppy-seed bun, topped with a medley of pickles, onions, mustard and—crucially—no ketchup allowed. For a lauded hotdog stop, check out Jimmy’s Red Hots.

For a change of culinary pace, neighboring state Michigan is an agricultural hotspot particuarly famous for its fruit. For a unique foodie experience, stay at Goldberry Woods and explore its 30 acres of orchards and hop houses. You’ll enjoy farm-to-table meals and a calendar of food-inspired classes and events.

Granor Farm is a certified organic farm where you can also enjoy an in-season multi-course, family-style meal (advanced booking required). Two excellent farm-to-table options on the state’s Upper Peninsula are Farm Club (who grow 90 percent of the vegetables and herbs they serve) and Pond Hill Farm (homemade pizzas and the estate’s own beer and wine).

Downtown Chicago’s upscale offerings are as impressive as its skyline. Chicago Cultural Centre features the opulent Tiffany Dome, with free tours run year-round. Handcrafted in 1897, the dome is the largest in the world of its kind, featuring more than 1,000 square feet of ornate Tiffany Favrile glass. Sunlight casts a kaleidoscope of colors through each of the 30,000 pieces.

Just a few blocks away you’ll find a hotly anticipated entry to the city’s luxury hotel scene, St Regis Chicago. The tallest building in the world designed by a female architect (Jeanne Gang), it’s luxe in every way imaginable: a world-class spa, unrivaled waterfront views and butlers for every room (yes, even at entry level).

For Chicago’s most sought-after fine dining experience, take a short cab ride over to Oriole in the West Loop neighborhood. This two-Michelin starred restaurant serves a menu of contemporary American cuisine alongside inventive cocktails and an impeccable wine list.

If an upscale road trip to the Great Lakes is on the cards, consider a stop at the seaside town of Saugatuck. Known as the Art Coast of Michigan, you’ll find galleries and artists’ studios to explore, as well as renowned wineries such as Modales. Bowdie’s Chophouse is the fine dining eatery in town, while The Southerner is famous for fried chicken with a fancy spin.

In the heart of Chicago’s Loop is the magnificent Millennium Park, 25 acres of gardens where locals and tourists gather year-round for picnics, free events and the iconic sculptures dotted throughout. A trip isn’t complete without a photo at Cloud Gate, known affectionately as ‘The Bean’. Inspired by liquid mercury, the impressive sculpture by British artist Anish Kapoor is one of the world’s largest permanent outdoor installations. You may recognize ‘The Bean’ from its film and TV show cameos; it’s been spotted in The Vow, Transformers: Age of Extinction and Parks and Recreation. Admire the reflections of the skyline (and yourself) in its shiny surface.

Chicago’s architectural history is a joy to explore—after all, it is the birthplace of the skyscraper. Less than half a mile from Millennium park is the Chicago Architecture Center, where you can explore exhibitions before setting off on one of the center’s renowned guided walking tours.

Four-and-a-half hours away by car, Michigan’s largest city Detroit is home to two world-renowned museums, each iconic in their own way. The Motown Museum will delight music fans with its celebration of the transformative record label that released artists such as The Supremes, Stevie Wonder and Marvin Gaye. While The Henry Ford is the largest museum complex in the United States and home to three distinct experiences. Take your pick of the Henry Ford Museum of American Innovation, the recreated history scenes of Greenfield Village or the Ford Rouge Factory Tour, which includes a visit to a working car plant—or visit all three with a longer stay and an ‘All Access’ ticket.

If you’ve been impressed by Lake Michigan’s beaches in Chicago, the 35 miles of pristine National Park shoreline at Sleeping Bear Dunes in the state of Michigan is likely to blow you away. The drive takes more than five hours from Chicago but you’ll arrive at otherworldly beauty, in the form of 400-foot towering sand dunes and turquoise-blue water. Stay in the nearby village of Empire and get a feel for the area by doing the Pierce Stocking Scenic Drive, a 7.4-mile loop with 12 clearly marked stops. For epic views, the Empire Bluff Trail is a 1.5-mile must-do hike.

It may be tempting to freewheel down the sand at the Dune Climb but beware it’s a steep and strenuous 30-minute ascent that challenges even the fittest of climbers. And while the beachy scenes are Caribbean-like in the summer months, from November to March the area is snow-covered. Visit for a different kind of tranquil beauty, as well as sledding and other winter activities.

For serenity closer to Chicago, make the worthwhile two-hour drive to Rockford, Illinois. Bountiful greenery earned its nicknames ‘The Forest City’ and ‘City of Gardens’. Case in point, the Anderson Japanese Gardens, a 12-acre oasis of streams, waterfalls and winding paths. Nothing settles the soul like an afternoon among the koi-filled ponds.

While you’re in Rockford, visit Laurent House—a stunning Mid-Century marvel by architect Frank Lloyd Wright. Designed for World War II veteran Kenneth Laurent, it’s the only Wright house built with wheelchair accessibility in mind. Book a tour to see one of his best-preserved homes.

Reachable in less than an hour by car from downtown, Kankakee River State Park is close enough for a nature-filled day-trip from Chicago. Though with excellent biking and hiking trails, fishing and horseback riding on offer, you may want to stay longer. The 1.5-mile trail that begins at the Visitor Center is flat, paved and shaded, making it a convenient way to immerse yourself in the pretty landscape.

Galien River County Park, 90 minutes east of Chicago, is home to two unique nature experiences. The first, a canopy walkway over the treetops leading to a lookout tower with sublime views. The other, a boardwalk over marshland, bringing you up close to wildlife such as turtles and herons. Both walks are accessible to wheelchairs and strollers.

However, you don’t need to leave the city to enjoy the great outdoors. Chicago is home to 28 miles of Lake Michigan shoreline and one of the USA’s finest beaches is just 10 minutes’ drive out of the city. Take in the majestic views at Oak Street Beach with lounge chairs, umbrellas and cabanas available for rent.

Lake Michigan is part of the largest freshwater system in the world, more famously known as the Great Lakes. The five connected lakes contain 20 percent of the world’s fresh water in an area roughly the size of the UK. To see more of this natural marvel, neighboring state Michigan is known as the “Great Lakes State” and is the only state to touch four of the lakes: Superior, Michigan, Huron and Erie. Home to five National Parks, including the renowned Sleeping Bear Dunes, Michigan has plenty to offer nature lovers.