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Amazing Day Trips from Chicago

Viewed by 144 travelers

Day 1: Explore Lake Geneva

Lake Geneva, Wisconsin

8:00AM

Breakfast at Egg Harbor Cafe

Start your day with a hearty breakfast at Egg Harbor Cafe, known for its delicious omelets and freshly squeezed juices.
Head northwest on I-90 and later merge onto WI-50 W towards Lake Geneva.
USD15, 1 hour

9:30AM

Lake Geneva Boat Tour

Embark on a scenic boat tour of Lake Geneva, where you can enjoy stunning views of the shoreline and historic mansions.
The boat tour departure point is just a short walk from the cafe.
USD30, 1.5 hours

11:00AM

Explore the Lake Geneva Shore Path

After the boat tour, stroll the picturesque Lake Geneva Shore Path, which boasts beautiful scenery and a peek at lavish lakeside homes.
Walk east from the boat dock to the shore path entrance.
Free, 2 hours

1:00PM

Lunch at The Boathouse

Savor a lakeside lunch at The Boathouse, offering fresh and locally sourced dishes alongside a great view.
Located right next to the Shore Path, you can easily walk there.
USD25, 1 hour

2:30PM

Visit the Geneva Lake Museum

Learn about the rich history of Lake Geneva at the Geneva Lake Museum, featuring engaging exhibits.
Drive or walk to the museum located in downtown Lake Geneva.
USD12, 1 hour

4:00PM

Wine Tasting at Studio Winery

Relax with a wine tasting experience at Studio Winery, where you can enjoy local wines and scenic views.
A short drive from the museum to Studio Winery.
USD15, 1.5 hours

6:00PM

Dinner at The Geneva Inn

Finish your day with an elegant dinner at The Geneva Inn, enjoying fine cuisine and sunset views over the lake.
It's a short drive or a lovely stroll along the lakeside to reach the restaurant.
USD50, 1.5 hours

8:00PM

Return to Chicago

Head back to Chicago after a fabulous day spent in Lake Geneva, reminiscing about the day’s adventures.
Drive back to Chicago via the same route.
Gas approximately USD20, 1.5 hours
Find Hotels in Lake Geneva

Day 2: Journey to Galena

Galena, Illinois

8:00AM

Breakfast at The Market House

Kick-start your day with breakfast at The Market House, famous for its extensive menu and homemade pastries.
Drive to Galena, about a 3-hour trip; enjoy the scenery along the way.
USD20, 1.5 hours

9:30AM

Visit Ulysses S. Grant Home

After breakfast, tour the historic Ulysses S. Grant Home, the former residence of the 18th President of the U.S.
It's a short drive from The Market House, easy to locate in Galena.
Free, 1 hour

10:30AM

Explore Main Street

Wander down Galena’s picturesque Main Street, lined with charming shops, galleries, and antique stores.
Walk from the Grant Home as Main Street is nearby.
Free, 2 hours

12:30PM

Lunch at Fried Green Tomatoes

Indulge in a local favorite at Fried Green Tomatoes, famous for its comfort food and friendly atmosphere.
Take a short walk from Main Street to the restaurant.
USD25, 1 hour

2:00PM

Visit Galena History Museum

Discover the rich history of Galena at the Galena History Museum, with exhibits on local heritage.
Drive or walk to the museum, located near the center of town.
USD10, 1 hour

3:00PM

Wine Tasting at Galena Cellars Vineyard

Enjoy an afternoon of wine tasting at Galena Cellars Vineyard, sampling local vintages in a lovely setting.
A short drive from the museum to the vineyard.
USD15, 1.5 hours

4:30PM

Visit Belvedere Mansion

End the day with a tour of the Belvedere Mansion, known for its beautiful architecture and stunning gardens.
A brief drive from the vineyard to the mansion.
USD15, 1 hour

6:00PM

Dinner at The Galena Lodge Restaurant

Wrap up your Galena getaway with a delightful dinner at The Galena Lodge Restaurant, featuring farm-to-table dishes.
A quick drive back to the lodge from the Belvedere Mansion.
USD40, 1.5 hours

8:00PM

Return to Chicago

Conclude your trip, reflecting on the wonderful experiences during your days away from the city.
Drive back to Chicago, about a three-hour drive.
Gas approximately USD30, 3 hours
Find Hotels in Galena
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