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16 Mar 2025Updated last time
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Chicago to Minneapolis Road Trip Itinerary

Chicago to Minneapolis Road Trip Overview

Embark on an unforgettable road trip from Chicago to Minneapolis that takes you through a diverse array of charming towns and vibrant cities. Begin your journey in the bustling metropolis of Chicago, IL, where you can explore world-class museums, savor a vibrant food scene, and marvel at iconic architecture such as the Willis Tower and Millennium Park's Cloud Gate. Continue your adventure to Rockford, IL, known for its beautiful parks like the Anderson Japanese Gardens and cultural attractions including the Rockford Art Museum.

Next, head to Madison, WI, which boasts a lively atmosphere with its numerous lakes, the impressive Wisconsin State Capitol, and the picturesque campus of the University of Wisconsin-Madison. From there, visit Wisconsin Dells, WI, famous for its stunning natural scenery, thrilling water parks, and various entertainment options, making it an excellent destination for family fun. Journey onward to La Crosse, WI, a city offering breathtaking riverfront views along the Mississippi River, charming downtown areas, and outdoor activities like hiking at Grandad Bluff.

Your trip continues to Rochester, MN, renowned for the Mayo Clinic, beautiful parks such as Silver Lake, and a rich cultural scene with museums and historic sites. Finally, reach your destination, Minneapolis, MN, where you can enjoy a unique blend of natural beauty, vibrant arts and music scenes, and notable attractions like the Minneapolis Sculpture Garden and the Mall of America. This road trip promises an enriching experience filled with diverse landscapes, cultural treasures, and memorable adventures.


Recommended Activities

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    Chicago, IL

    Chicago offers world-class museums, a vibrant food scene, beautiful lakeside views, and iconic architecture such as the Willis Tower and Millennium Park's Cloud Gate.
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    Rockford, IL

    Rockford is known for its beautiful parks, including Anderson Japanese Gardens, and cultural attractions like the Rockford Art Museum.
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    Madison, WI

    Madison boasts a lively atmosphere with its numerous lakes, the lovely Wisconsin State Capitol, and the University of Wisconsin-Madison's picturesque campus.
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    Wisconsin Dells, WI

    Wisconsin Dells is famous for its stunning natural scenery, thrilling water parks, and various entertainment options, making it a great destination for family fun.
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    La Crosse, WI

    La Crosse offers beautiful riverfront views along the Mississippi River, charming downtown areas, and outdoor activities like hiking Grandad Bluff.
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    Rochester, MN

    Rochester is renowned for the Mayo Clinic, beautiful parks like Silver Lake, and a rich cultural scene with museums and historic sites.
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    Minneapolis, MN

    Minneapolis offers a unique blend of natural beauty with its numerous parks and lakes, vibrant arts and music scenes, and attractions like the Minneapolis Sculpture Garden and the Mall of America.
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Restaurants

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    Alinea (Chicago, Illinois)

    4.6
    $$$$

    Alinea (Chicago, Illinois)

    Alinea in Chicago offers a unique, avant-garde dining experience with innovative multi-course tasting menus.
    4.6
    $$$$
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    Beef-A-Roo

    4.3
    $$$$

    Beef-A-Roo

    A quirky, local favorite in Rockford, IL, known for its retro vibe and delicious roast beef sandwiches.
    4.3
    $$$$
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    The Old Fashioned (Madison, WI)

    The Old Fashioned (Madison, WI)

    Located in Madison, WI, this restaurant celebrates Wisconsin's culinary traditions with locally sourced ingredients and classic dishes.
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    Ishnala Supper Club

    4.6
    $$$$

    Ishnala Supper Club

    Situated in Wisconsin Dells, this restaurant offers a historic ambiance and scenic views of Mirror Lake.
    4.6
    $$$$
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    The Vintage Kitchen

    The Vintage Kitchen

    A charming spot in La Crosse, WI, known for its eclectic decor and farm-to-table cuisine.
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Hotels

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    The Gwen, a Luxury Collection Hotel

    The Gwen, a Luxury Collection Hotel

    Located in Chicago, this hotel provides an art deco experience with lavish decor and top-notch amenities.
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    Ironworks Hotel

    4.6

    Ironworks Hotel

    Situated in Beloit, WI, this boutique hotel features industrial-chic design and a warm, inviting atmosphere.
    4.6
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    Graduate Madison

    4.1

    Graduate Madison

    This quirky, college-themed hotel in Madison, WI, offers a nostalgia-filled experience with its fun and vibrant decor.
    4.1
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    Nordic Lodge

    3.9

    Nordic Lodge

    Located in Sister Bay, WI, this charming Scandinavian-inspired lodge offers a cozy and unique stay with a Northern European touch.
    3.9
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    The Charmant Hotel

    4.7

    The Charmant Hotel

    A beautifully restored historic building in La Crosse, WI, offering luxury accommodations and a rooftop bar with stunning river views.
    4.7
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Local Events & Happenings

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    Little River Band

    Little River Band

    The event will take place at Ho-Chunk Gaming-WI-Dells in Baraboo.
    Map IconHo-Chunk Gaming-WI-Dells in Baraboo (31.87 mi)
    Calendar Icon31 Aug 2025
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    Rodney Carrington

    Rodney Carrington

    The event will take place at Ho-Chunk Gaming-WI-Dells in Baraboo.
    Map IconHo-Chunk Gaming-WI-Dells in Baraboo (31.87 mi)
    Calendar Icon14 Sep 2025
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    Grand Funk Railroad

    Grand Funk Railroad

    The event will take place at Ho-Chunk Gaming-WI-Dells in Baraboo.
    Map IconHo-Chunk Gaming-WI-Dells in Baraboo (31.87 mi)
    Calendar Icon26 Oct 2025
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    Country Boom Music Festival

    Country Boom Music Festival

    The event will take place at Country Boom in West Salem.
    Map IconCountry Boom in West Salem (49.22 mi)
    Calendar IconN/A
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    Elvis Explosion

    Elvis Explosion

    Elvis Explosion Package Tickets are On Sale May 15 at 11 AM until June 15. Individual Event Tickets are On Sale June 16 at 11 AM.
    Map IconLa Crosse Center in La Crosse (52.29 mi)
    Calendar Icon6 Sep 2025
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    Elvis Explosion Package

    Elvis Explosion Package

    Elvis Explosion Package Tickets are On Sale May 15 at 11 AM until June 15. Individual Event Tickets are On Sale June 16 at 11 AM.
    Map IconLa Crosse Center in La Crosse (52.29 mi)
    Calendar Icon6 Sep 2025
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    Born of Osiris, The Browning , AXTY, Lost in Separation

    Born of Osiris, The Browning , AXTY, Lost in Separation

    The event will take place at The Annex in Madison.
    Map IconThe Annex in Madison (54.16 mi)
    Calendar Icon25 Sep 2025
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Travel Gems from Reddit


Music for Your Journey

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    Rascal Flatts - Life is a Highway

    Rascal Flatts - Life is a Highway

    Perfect for road trips with its upbeat tempo and adventurous spirit.
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    Eagles - Take It Easy - 2013 Remaster

    Eagles - Take It Easy - 2013 Remaster

    A classic rock tune that captures the essence of a laid-back journey.
    Listen on Spotify
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    Chuck Berry - Route 66

    Chuck Berry - Route 66

    An iconic road trip anthem celebrating the famous highway.
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    Willie Nelson - On The Road Again - Live

    Willie Nelson - On The Road Again - Live

    Willie Nelson's classic hit embodies the freedom of traveling.
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    Bruce Springsteen - Born to Run

    Bruce Springsteen - Born to Run

    A high-energy song that's perfect for fueling your driving excitement.
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    Lindsey Buckingham - Holiday Road - National Lampoon's Vacation

    Lindsey Buckingham - Holiday Road - National Lampoon's Vacation

    A fun and nostalgic road trip song featured in National Lampoon’s Vacation.
    Listen on Spotify
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    Tom Petty - Runnin' Down A Dream

    Tom Petty - Runnin' Down A Dream

    Tom Petty's song about ambition and the open road.
    Listen on Spotify
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    Fleetwood Mac - Go Your Own Way - 2004 Remaster

    Fleetwood Mac - Go Your Own Way - 2004 Remaster

    A Fleetwood Mac classic about independence and moving forward.
    Listen on Spotify
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    Incubus - Drive

    Incubus - Drive

    An evocative song with a mellow vibe for stretches of scenic driving.
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    Robert Johnson - Sweet Home Chicago

    Robert Johnson - Sweet Home Chicago

    A tribute to Chicago, perfect for starting your journey.
    Listen on Spotify
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