At a glance
Scan the table to match a trip to your weekend. Traffic and schedules change, so check before you go.
| Trip | Getting there | Best for | Start with |
|---|
| Milwaukee, WI | Amtrak Hiawatha, 1 hour 29 minutes, with round-trips daily including Sunday. | A lakefront city with museums and theaters | The Milwaukee Art Museum |
| Madison, WI | FlixBus, with trips from 3 hours 20 minutes. | Lakes, a campus and live shows | Memorial Union Terrace |
| St. Joseph, MI | Amtrak Pere Marquette, or about 1.5 hours by car. | A beach day by the water | Silver Beach County Park |
| Indiana Dunes, IN | The South Shore Line stops at four stations in the park. | Beaches and hiking | Dune Park station and the Visitor Center |
| Galena, IL | Drive: 3 hours. | A historic small town with outdoor days | Ulysses S. Grant's home |
| Starved Rock, IL | Starved Rock Lodge says less than two hours from Chicago. | Canyons and waterfalls | The park's canyon trails |
| Door County, WI | Drive: 4 hours 15 minutes to Sturgeon Bay. | State parks and lighthouses on a peninsula | Peninsula State Park |
Trips with train or bus service
Milwaukee, WI
A lakefront city a short train ride away, with a landmark art museum and a theater district.
- Getting there. Amtrak's Hiawatha runs multiple round-trips daily between Chicago and Milwaukee, including Sunday. Amtrak lists the trip at 1 hour 29 minutes and says you can be in the center of either city in a quick 90 minutes. The Quiet Car is available on all Hiawatha trains.
- Day one. Start with breakfast at Uncle Wolfie's Breakfast Tavern, then take a short walk for views of the downtown skyline. Visit The Pfister Hotel, built in 1893, which has the largest Victorian art collection of any hotel in the world. For lunch, try Pepperpot on MLK, known for its jerk egg rolls, oxtail and jerk chicken.
- Day two. Head to the lakefront and the Milwaukee Art Museum. Its Calatrava-designed Quadracci Pavilion is the city's defining landmark, and the Burke Brise Soleil opens daily and flaps at noon, weather permitting. Inside are a large collection of Haitian art and one of the largest Georgia O'Keeffe collections outside New Mexico. The Milwaukee Theater District is just blocks away for an evening show, and At Random in Bay View, an institution since 1964, makes a good nightcap.
- Worth knowing. Plan how you will get from the station to the lakefront and to Bay View.
Madison, WI
A capital city built around two lakes, with a lively campus and downtown.
- Getting there. FlixBus runs between Chicago and Madison, with trips from 3 hours 20 minutes. Check the weekend departures and the stop you want before you book.
- Day one. Go to the Memorial Union Terrace on the UW–Madison campus, known for its views of Lake Mendota and its sunburst chairs. Then take a guided tour of Monona Terrace to learn about Frank Lloyd Wright's vision for the city and Lake Monona. Rent a kayak, canoe or paddleboard at Brittingham Boats or through Outdoor UW at the Terrace.
- Day two. Visit the Madison Museum of Contemporary Art or the Chazen Museum of Art, then rent an e-bike from a Madison BCycle station and explore the city's trails. In the evening, see a show at the Overture Center for the Arts, Comedy on State or the historic Orpheum Theater.
- Worth knowing. In summer, outdoor live music runs all through downtown, from the Monona Terrace rooftop to the Terrace.
St. Joseph, MI
A Lake Michigan beach town, with a train that stops close to the sand.
- Getting there. Amtrak's Pere Marquette runs from Chicago to Grand Rapids with a stop at St. Joseph, and Visit Southwest Michigan lists it Sunday through Saturday. The station is within walking distance of lodging and activities, and less than a five-minute walk from the beach. By car, Visit Southwest Michigan puts St. Joseph about 1.5 hours from Chicago, non-stop.
- Day one. Walk to Silver Beach County Park, with 1,600 feet of sandy shoreline, a boardwalk and a pavilion. Stroll out onto the South Pier to watch boats and freighters come in, and look across at the North Pier lighthouses. Stay for sunset.
- Day two. Rent a stand-up paddleboard or kayak from Third Coast Paddling, which has locations at Silver Beach, Jean Klock Park and the Paw Paw River. Silver Beach also has loungeboards, skimboards and beach umbrellas.
- Worth knowing. Lifeguards are on duty at Silver Beach in the summer. Construction on I-94 can affect drive times.
Indiana Dunes, IN
Miles of Lake Michigan beach and dune trails, with train stops inside the park.
- Getting there. The South Shore Railroad stops at four stations throughout the park. From the Dune Park station, the Indiana Dunes Visitor Center is a 1.33-mile walk or ride south on the Dunes Kankakee Trail. Select weekend trains allow bikes, and Dune Park is the only stop in the park that does.
- Day one. Pick up a map at the Visitor Center and head to the beach. Indiana Dunes National Park is a 13,000-acre preserve stretching 15 miles along the lake, with hiking trails, beaches and historic sites.
- Day two. Spend it on the trails, or visit Indiana Dunes State Park, which covers more than 2,000 acres. Both parks have designated campsites within walking distance of the beach.
- Worth knowing. The larger beaches can get crowded on summer weekends, so go early in the day. Fall, winter and spring bring easier parking and a different feel: hiking in fall and sledding on the dunes in snow. West Beach is the only part of the national park with an entrance fee, and the state park charges at its gate.
Trips worth the drive
Galena, IL
A historic small town with more than 125 shops and restaurants, plus ziplines, fly-fishing and resort slopes.
- Getting there. Enjoy Illinois lists Chicago to Galena as 3 hours by automobile.
- Day one. Walk the historic downtown, with more than 125 shops and restaurants, including Fried Green Tomatoes and Otto's Place Cafe. Tour President Ulysses S. Grant's home.
- Day two. Get outdoors. Zip over the trees with Long Hollow Canopy Tours, or try its aerial Adventure Park. Galena Fly Fishing Outfitters provides equipment, instruction and transportation for half-day and full-day trips. At Chestnut Mountain Resort you can ride the dual alpine slides or the Farside Gravity Bike Park.
- Worth knowing. Eagle Ridge Resort and Spa and Chestnut Mountain Resort are the two resorts, and Eagle Ridge has four premier golf courses.
Starved Rock, IL
Sandstone canyons and waterfalls along the Illinois River, with a historic lodge in the park.
- Getting there. Starved Rock Lodge, in Oglesby, says it is less than two hours from Chicago.
- Day one. Walk the canyon trails. The park has 18 canyons with moss-covered sandstone walls, more than 13 miles of trails, rain-fed waterfalls and overhangs. Spend the night at the historic Starved Rock Lodge, built in the 1930s, which offers lodge rooms, log cabins and hotel rooms, and have dinner at the Lodge Restaurant.
- Day two. Start at the visitor center, where the exhibit hall, park office and information desk are open 9 a.m. to 4 p.m. daily. Then pick a trail to a canyon or a viewpoint, or join one of the guided tours and programs the park hosts through the year.
- Worth knowing. Throughout 2026, some trails could be closed or have limited access because of a trail improvement project. The lodge, campground and visitor center stay open. Check Illinois DNR's trail updates before you go.
Door County, WI
A peninsula with five state parks and 11 historic lighthouses. It is the longest drive here, so plan to stay put.
- Getting there. Destination Door County lists the drive from Chicago to Sturgeon Bay as four hours and fifteen minutes: north on I-94, onto I-43 in Milwaukee, then exit 185 onto Highway 57. Once you are there, Door 2 Door Rides runs a shared-ride connector in Sturgeon Bay and northern Door County.
- Day one. Hike the bluffs of Peninsula State Park. In Ephraim, the Old Post Office Restaurant serves a Door County fish boil of fresh whitefish nightly Monday through Saturday, and holiday Sundays. Reservations are requested.
- Day two. Explore the rugged coast at Newport State Park and the waves at Whitefish Dunes. Or have breakfast at the Old Post Office Restaurant, where cherry pancakes and Belgian waffles are on the menu.
- Worth knowing. Door County has more than 300 miles of shoreline, so pick one stretch of the peninsula rather than trying to see it all. The Old Post Office Restaurant is open May to October and closed in winter, so check seasonal hours.
