Scenic Road Trip from Chicago to Minnesota: A Midwest Adventure

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Day 1: Chicago to Madison

Chicago, IL to Madison, WI on May 17, 2025

7:30am

Breakfast at Ann Sather

Enjoy classic Swedish cinnamon rolls and hearty breakfast options at this beloved Chicago staple, opening at 7:00am, perfect to fuel up before hitting the road.
USD20, 1h0m

8:30am

Drive to Madison, Wisconsin

Depart Chicago and embark on a 2.5-hour drive northwest via I-90 W, enjoying scenic views of the Midwestern countryside.
USD0, 2h30m

11:00am

Explore Wisconsin State Capitol

Visit the iconic Wisconsin State Capitol in Madison, known for its stunning architecture and beautiful murals, open to the public weekdays 8:00am–6:00pm.
USD0, 1h0m

12:30pm

Lunch at The Old Fashioned

Savor classic Wisconsin comfort food and local brews in a lively atmosphere, open from 11:00am to 9:00pm.
USD25, 1h0m

2:00pm

Visit Olbrich Botanical Gardens

Explore the vibrant outdoor gardens and tropical conservatory, a perfect spot for a leisurely stroll open daily from 10:00am to 6:00pm.
USD0, 1h30m

4:00pm

Check into hotel in Madison

Relax and freshen up before dinner. Choose a centrally located hotel for easy access to dining and evening walks.
USD150, 1h0m

6:30pm

Dinner at Graze

Dine at a popular farm-to-table restaurant offering innovative shared plates and beautiful views of the Capitol, open until 10:00pm.
USD35, 1h30m
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Day 2: Madison to Minneapolis

Madison, WI to Minneapolis, MN on May 18, 2025

7:30am

Breakfast at Marigold Kitchen

Start the day with light and fresh breakfast options, including pastries and coffee, open at 7:00am.
USD15, 1h0m

8:30am

Drive to Minneapolis

Continue the trip heading northwest for about 4 hours, passing scenic spots along I-94 W.
USD0, 4h0m

12:30pm

Lunch at Midtown Global Market

Enjoy diverse ethnic food stalls in this vibrant indoor market, perfect for a quick and tasty meal, open 10:00am to 6:00pm.
USD20, 1h0m

2:00pm

Visit Minneapolis Sculpture Garden

Walk through one of the largest urban sculpture gardens in the US, featuring iconic pieces like the Spoonbridge and Cherry, open daily from 6:00am to midnight.
USD0, 1h0m

3:30pm

Explore the Walker Art Center

Visit a leading contemporary art museum adjacent to the Sculpture Garden, open from 11:00am to 5:00pm on Saturdays.
USD25, 1h30m

5:30pm

Check into Minneapolis hotel

Settle into your accommodation in downtown Minneapolis.
USD180, 1h0m

7:00pm

Dinner at The Bachelor Farmer

Experience Nordic-inspired dishes made from local ingredients in a charming setting, open until 9:00pm on Saturdays.
USD40, 1h30m
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Day 3: Explore Minneapolis / St. Paul

Minneapolis and St. Paul, MN on May 19, 2025

8:00am

Breakfast at Pur-0-Misu

Enjoy artisan coffee and fresh breakfast fare in the Whittier neighborhood, opening at 7:00am.
USD15, 1h0m

9:30am

Visit the Minnesota State Capitol

Tour the grand building with its beautiful dome in St. Paul, open Monday to Friday 8:00am-4:30pm, weekends closed, so this visit is best on a weekday or take an external walk around the grounds.
USD0, 1h0m

11:00am

Walk around Como Park Zoo & Conservatory

Visit this free zoo and conservatory featuring variety of animals and beautiful indoor gardens, open 10:00am–4:00pm on weekends.
USD0, 2h0m

1:00pm

Lunch at The Lexington

Discover one of St. Paul's oldest restaurants with classic American meals and local charm, open daily for lunch and dinner.
USD25, 1h0m

3:00pm

Stroll along the Mississippi Riverfront

Experience scenic views and walking paths along the river, ideal for a relaxing afternoon walk.
USD0, 1h0m

5:00pm

Return to Minneapolis / Relax

Rest at your accommodation or explore local shops and cafes.
USD0, 1h0m

7:00pm

Dinner at Spoon and Stable

End your trip with a fine dining experience featuring contemporary American cuisine in a beautifully restored stable, open until 9:00pm on Mondays.
USD50, 1h30m
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Itinerary created by AI-assisted, human-reviewed