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20 Oct 2025
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10 best places for weekend getaways from Naperville, IL

Weekend Getaways from Naperville, IL: Trip Itinerary Overview

Embark on a rewarding journey beyond Naperville with this thoughtfully curated collection of the ten best weekend getaway destinations. Whether you love nature, history, or simply want to unwind, this itinerary promises a mix of scenic landscapes, cultural highlights, and unique experiences suited for all interests. Discover the dramatic canyons and waterfalls of Starved Rock State Park, and take in the tranquility of Matthiessen State Park, both perfect for outdoor adventure and relaxation. Explore the lush gardens and educational paths at Morton Arboretum and Cantigny Park, where natural beauty meets family-friendly activities.

Venture farther to the sandy shores and diverse ecosystems of Indiana Dunes National Park, ideal for beach lovers and hikers. Stroll along the picturesque Lake Geneva Shore Path with its breathtaking lake views and historic estates. Immerse yourself in vibrant floral displays at Chicago Botanic Garden and the peaceful serenity of Anderson Japanese Gardens. Step back in time in Galena Historic District, where charming streets and historic architecture abound. And don’t miss Millennium Park in downtown Chicago, the city’s social and cultural hub, featuring iconic attractions like Cloud Gate and lively public events. This itinerary offers a perfect blend of discovery, recreation, and memorable experiences.


Recommended Activities

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    Starved Rock State Park

    Famous for its striking canyons, scenic overlooks of the Illinois River, and beautiful waterfalls, it's perfect for hiking and photography.
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    Morton Arboretum

    This expansive outdoor museum features diverse tree collections, themed gardens, hiking trails, and interactive exhibits, making it ideal for nature lovers and families alike.
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    Matthiessen State Park

    Known for its dramatic rock formations, lush woods, and picturesque waterfalls, it's a peaceful destination for hiking, picnicking, and wildlife spotting.
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    Cantigny Park

    Offers beautifully landscaped gardens, fascinating military museums, and family-friendly activities in a peaceful, historic estate setting.
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    Indiana Dunes National Park

    Features diverse ecosystems, sandy beaches along Lake Michigan, scenic hiking trails, and unique wildlife, making it a haven for outdoor enthusiasts.
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    Lake Geneva Shore Path

    Provides picturesque views of historic estates and crystal-clear waters, making it perfect for leisurely walks and soaking in the lakefront charm.
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    Chicago Botanic Garden

    Showcases breathtaking themed gardens, peaceful walking paths, and educational exhibits, perfect for plant lovers and anyone seeking a tranquil escape.
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    Anderson Japanese Gardens

    Renowned for its authentic, meticulously designed Japanese landscapes, serene koi ponds, and calming atmosphere ideal for relaxation and reflection.
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    Galena Historic District

    Famous for its preserved 19th-century architecture, charming shops, and rich history, offering an immersive experience in a picturesque small-town setting.
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    Millennium Park

    Home to iconic attractions like Cloud Gate ('The Bean'), impressive public art, beautiful gardens, and free outdoor concerts, making it a vibrant centerpiece of downtown Chicago.
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Restaurants

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    The Girl & The Goat

    The Girl & The Goat

    A celebrated Chicago hotspot known for inventive shared plates led by award-winning chef Stephanie Izard, offering a lively urban dining experience.
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    Frontera Grill

    8.8
    $$$$

    Frontera Grill

    Rick Bayless’s acclaimed restaurant serving upscale Mexican cuisine with bold flavors and locally sourced ingredients.
    8.8
    $$$$
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    Parachute

    8.7
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    Parachute

    A Michelin-starred, modern Korean-American restaurant in Chicago, praised for its creative dishes and intimate setting.
    8.7
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    The Publican - Chicago, IL

    4.5
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    The Publican - Chicago, IL

    Renowned for its hearty, farm-to-table fare with a focus on pork and beer, housed in a stylish communal space in Chicago’s Fulton Market.
    4.5
    $$$$
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    Luella’s Southern Kitchen

    4.4
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    Luella’s Southern Kitchen

    A beloved spot in Lincoln Square offering authentic Southern comfort food and warm hospitality.
    4.4
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Hotels

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    The Langham, Chicago

    The Langham, Chicago

    Luxury hotel with elegant rooms, excellent river views, and top-notch amenities in downtown Chicago.
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    Grand Geneva Resort & Spa

    Grand Geneva Resort & Spa

    Expansive resort in Lake Geneva featuring golf courses, a spa, and various recreational activities, perfect for a relaxing getaway.
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    Hotel Arista

    Hotel Arista

    Modern, upscale hotel in Naperville known for sleek design, exceptional service, and easy access to local attractions.
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    Hotel Julien Dubuque

    Hotel Julien Dubuque

    Historic hotel in the heart of downtown Dubuque, close to the Galena Historic District, blending classic charm with modern amenities.
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    Starved Rock Lodge

    4.5

    Starved Rock Lodge

    Rustic lodge offering comfortable accommodation within Starved Rock State Park, ideal for nature lovers and hikers.
    4.5
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Local Events & Happenings

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    Gladys Knight

    Gladys Knight

    The event will take place at Arcada Theatre in Saint Charles.
    Map IconArcada Theatre in Saint Charles (8.97 mi)
    Calendar Icon14 Nov 2025
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    The Marshall Tucker Band

    The Marshall Tucker Band

    The event will take place at Arcada Theatre in Saint Charles.
    Map IconArcada Theatre in Saint Charles (8.97 mi)
    Calendar Icon21 Nov 2025
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    Loverboy

    Loverboy

    The event will take place at Arcada Theatre in Saint Charles.
    Map IconArcada Theatre in Saint Charles (8.97 mi)
    Calendar Icon4 Dec 2025
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    A Timeless Christmas with The Lettermen

    A Timeless Christmas with The Lettermen

    The event will take place at Arcada Theatre in Saint Charles.
    Map IconArcada Theatre in Saint Charles (8.97 mi)
    Calendar Icon11 Dec 2025
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    Steel Panther

    Steel Panther

    The event will take place at Arcada Theatre in Saint Charles.
    Map IconArcada Theatre in Saint Charles (8.97 mi)
    Calendar Icon18 Dec 2025
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    Sara Evans

    Sara Evans

    The event will take place at Arcada Theatre in Saint Charles.
    Map IconArcada Theatre in Saint Charles (8.97 mi)
    Calendar Icon21 Dec 2025
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    Ten Years After

    Ten Years After

    The event will take place at Arcada Theatre in Saint Charles.
    Map IconArcada Theatre in Saint Charles (8.97 mi)
    Calendar IconN/A
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Travel Gems from Reddit

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    Unfortunately, Naperville is mostly chain restaurants, but there are still some good places. u/katbonk mentioned Naper Settlement which is mostly closed for the season until A...

    My friend and I are spending the weekend in Naperville. What to do?

    Unfortunately, Naperville is mostly chain restaurants, but there are still some good places. u/katbonk mentioned Naper Settlement which is mostly closed for the season until A...

    /r/Naperville
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    46 votes, 47 comments. Ive been trying to find somewhere the fianc and I can get away for a weekend that would be worthwhile. Im wanting to go

    Fun weekend getaways in Illinois or surrounding states?

    46 votes, 47 comments. Ive been trying to find somewhere the fianc and I can get away for a weekend that would be worthwhile. Im wanting to go

    /r/illinois
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    22 votes, 52 comments. Hey guys Im from the NW Burbs and was looking to do a little weekend getaway with me and my girlfriend. We have a pretty

    Little weekend getaway in illinois?

    22 votes, 52 comments. Hey guys Im from the NW Burbs and was looking to do a little weekend getaway with me and my girlfriend. We have a pretty

    /r/illinois
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    22 votes, 38 comments. I have spent plenty of weekends in Indiana, Michigan, Wisconsin, southern Illinois. Im looking to mix it up and try somewhere

    Where to travel for weekend trip?

    22 votes, 38 comments. I have spent plenty of weekends in Indiana, Michigan, Wisconsin, southern Illinois. Im looking to mix it up and try somewhere

    /r/illinois
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    Its kind of a long ride but I drive from Chicago to Nashville with my family if 5 for about 4 days and it was a ton of fun. My kids are between 1-6 ... Galena IL/ Mineral Poin...

    Can anyone suggest a 3-4 day weekend getaway from chicago?

    Its kind of a long ride but I drive from Chicago to Nashville with my family if 5 for about 4 days and it was a ton of fun. My kids are between 1-6 ... Galena IL/ Mineral Poin...

    /r/AskChicago

Music for Your Journey

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    Edward Sharpe & The Magnetic Zeros - Home

    Edward Sharpe & The Magnetic Zeros - Home

    A feel-good anthem about the joy of travel and returning home, perfect for starting your journey.
    Listen on Spotify
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    Willie Nelson - On The Road Again - Live

    Willie Nelson - On The Road Again - Live

    Classic road trip song that celebrates the excitement of hitting the open road.
    Listen on Spotify
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    Rusted Root - Send Me on My Way

    Rusted Root - Send Me on My Way

    Upbeat and cheerful, it adds a sense of adventure and optimism to your drive.
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    WALK THE MOON - Shut Up and Dance

    WALK THE MOON - Shut Up and Dance

    An energetic, catchy tune that’s sure to lift spirits and keep everyone moving.
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    Eagles - Take It Easy - 2013 Remaster

    Eagles - Take It Easy - 2013 Remaster

    A laid-back classic ideal for cruising scenic byways and relaxing on your trip.
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    Katrina & The Waves - Walking On Sunshine

    Katrina & The Waves - Walking On Sunshine

    Bright and lively, it brings sunny vibes and positivity to any travel playlist.
    Listen on Spotify
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    Rascal Flatts - Life is a Highway

    Rascal Flatts - Life is a Highway

    Embraces the spirit of exploration and makes for an iconic travel singalong.
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    Fleetwood Mac - Go Your Own Way - 2004 Remaster

    Fleetwood Mac - Go Your Own Way - 2004 Remaster

    Encourages freedom and adventure, fitting for exploring new destinations.
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    The B-52's - Roam

    The B-52's - Roam

    Celebrates the thrill of wandering and discovering new places during your journey.
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    Coldplay - Adventure of a Lifetime

    Coldplay - Adventure of a Lifetime

    An uplifting, energetic track that embodies the excitement of every great road trip.
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