1. Milwaukee (1 hour 35 minutes)
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Location:
Milwaukee, WIHighlights:
If you’re planning a city escape packed with character, culture, and crisp craft beers, we can’t recommend Milwaukee enough. It’s one of those places where history and modern vibes blend perfectly—ideal for weekend wanderers or festival fanatics.Recommended For:
Beer lovers, motorcycle enthusiasts, festivalgoers, history buffs, and travelers seeking a fun urban getaway with Midwest charm.What I Love: ♥
The vibrant brewery scene, legendary Harley-Davidson history, nonstop festivals, and a ton of green spaces for outdoor fun.- Explore Milwaukee’s proud brewing roots—from historic tours to creative microbreweries—thanks in part to the iconic 1960s Schlitz jingle that dubbed it "the beer that made Milwaukee famous."
- Visit the Harley-Davidson Museum to see the world’s oldest Harley and immerse yourself in motorcycle culture and innovation.
- Celebrate with the locals at over two dozen festivals, including Summerfest, the world’s largest music festival.
- Enjoy recreational bliss with access to 75 golf courses, 25 theaters, and 150 parks throughout the city.
Distance from Chicago:
Just under 2 hours by car or around 1.5 hours by Amtrak from downtown Chicago.How to Get to Milwaukee:
Milwaukee is easily reached by I-94 from Chicago, or via direct flights and Amtrak service to Milwaukee Intermodal Station.2. Holland, Michigan (2 hours 30 minutes)
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Location:
Holland, MIHighlights:
Looking for a getaway that feels like a European escape without leaving the Midwest? Holland, Michigan charms visitors year-round with vibrant tulip fields, windmills, Dutch treats, and festive small-town energy.Recommended For:
Garden lovers, culture seekers, families, photographers, and anyone who adores spring festivals or European flair.What I Love: ♥
The explosion of tulips in spring, the charming Dutch architecture, immersive cultural events, and authentic shops like the wooden shoe factory.- Experience the city’s rich Dutch heritage, the heart of its appeal, highlighted each year during the world-famous Tulip Time Festival in early May.
- Marvel at more than 4.5 million tulips in bloom across locations like Veldheer Tulip Gardens and Windmill Island Gardens.
- Celebrate Dutch culture with parades, traditional Klompen dancing, live music, and local cuisine during spring's main event or winter’s cozy Dutch Winterfest.
- Discover year-round attractions like authentic windmills, historic architecture, and the DeKlomp Wooden Shoe & Delft Factory, or browse Dutch art at the Holland Museum.
Distance from Chicago:
About 2.5 hours by car.How to Get to Holland, Michigan:
Take I-94 or I-196 from Chicago to Holland. The scenic drive hugs the Lake Michigan shoreline and is particularly beautiful in spring and fall.3. Kettle Moraine State Forest (2 hours 40 minutes)
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Location:
Campbellsport, WIHighlights:
If you're itching for fresh air, forested trails, and one of the most scenic drives in the Midwest, Kettle Moraine State Forest is the perfect weekend escape. It’s a massive, adventure-filled stretch of Wisconsin wilderness that lets you truly unplug and reconnect with nature.Recommended For:
Outdoor enthusiasts, hikers, road trippers, winter sports fans, families, and anyone seeking nature with a side of history.What I Love: ♥
The endless trails for every season, the picturesque Scenic Drive, and the unique mix of geological and cultural landmarks scattered across the forest.- Explore over 30,000 acres of forest with eleven designated-use trails for hiking, horseback riding, mountain biking, skiing, snowshoeing, and more.
- Drive the 115-mile Kettle Moraine Scenic Drive, created for day-trippers to enjoy the most breathtaking natural views and attractions.
- Visit cultural and historic stops along the route like the Wade House Stagecoach Inn, Holy Hill Basilica, and Old World Wisconsin Outdoor Museum.
- Discover 24 protected natural areas, geological wonders, and 17 quaint small towns as you meander through Wisconsin’s countryside.
Distance from Chicago:
Around 2.5 to 3 hours by car.How to Get to Kettle Moraine State Forest:
Take I-94 West from Chicago toward Milwaukee, then I-41 North to Highway 28. Follow signs toward Campbellsport and the forest’s Northern Unit. The scenic drive begins near Elkhart Lake and runs south through the area.Address:
N1765 Highway G, Campbellsport, WIPhone: 262-626-2116
4. Lake Geneva (1 hour 40 minutes)
© Lake Geneva
Location:
Lake Geneva, WIHighlights:
If you're craving a quick escape from the city without giving up lake views, Lake Geneva is like stepping into a lakeside resort storybook. It’s peaceful, upscale, and just far enough from Chicago to feel like a true retreat.Recommended For:
Couples, architecture buffs, shoppers, lake lovers, and anyone seeking a classy weekend away with a historical twist.What I Love: ♥
The walkable shoreline packed with Gilded Age mansions, scenic lake cruises, and the blend of small-town charm with sophisticated dining and shops.- Stroll or bike the 21-mile Lake Geneva Shore Path for an intimate look at historic mansions once owned by Chicago’s elite.
- Set sail with the Lake Geneva Cruise Line to view the lakeside estates from the water—especially stunning at sunset.
- Explore a vibrant downtown with eclectic boutiques, cozy cafés, fine dining, and lively local bars year-round.
- Relax in all seasons—Lake Geneva is as great for summer boating as it is for winter spa days, skiing, and cozy getaways.
Distance from Chicago:
Just under 1.5 hours by car.How to Get to Lake Geneva:
From Chicago, head north on I-94, then take Route 50 west to Lake Geneva. It’s a straight, easy drive ideal for day trips or quick weekend escapes.Romantic Day Trips from Chicago:
5. Naperville (40 minutes)
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Location:
Naperville, ILHighlights:
If you're looking for a quick getaway that blends small-town charm with scenic strolls and family fun, Naperville is a gem just outside the city. The Riverwalk alone is worth the trip—peaceful, picturesque, and packed with hidden surprises.Recommended For:
Families, couples, photographers, walkers, and anyone who enjoys a relaxing day filled with water views and local eats.What I Love: ♥
The charming DuPage Riverwalk, paddle boats, bell towers, Centennial Beach, and the peaceful, well-kept vibe of this walkable downtown area.- Walk the 1.75-mile Riverwalk—lined with fountains, bridges, heritage sculptures, a clock tower, and the stunning Moser Tower.
- Play at Centennial Beach and Grill, a family-friendly sandy waterpark with a beachside restaurant, ideal for summer fun and sun.
- Relax at riverside amphitheaters or test your balance through a meditative stroll in the Riverwalk’s labyrinth.
- Paddle along the DuPage River with paddle boat rentals for a laid-back way to take in the scenery.
Distance from Chicago:
Around 45 minutes to 1 hour by car or Metra train.How to Get to Naperville:
Take I-88 west or hop on the BNSF Metra line from Union Station to Naperville. Both options make it easy for a relaxed day trip.6. Village of Oak Park (15 minutes)
© Village of Oak Park
Location:
Oak Park, ILHighlights:
If you love architecture, artsy vibes, and welcoming communities, Oak Park should be at the top of your list. It’s the kind of place that feels progressive, creative, and deeply rooted in history all at once.Recommended For:
History lovers, architecture fans, LGBTQ+ travelers, weekend wanderers, and anyone seeking diversity, charm, and cultural depth close to Chicago.What I Love: ♥
The walkable Frank Lloyd Wright Historic District, inclusive spirit, boutique shops, and lush stops like the Oak Park Conservatory.- Tour the Frank Lloyd Wright District, home to an incredible concentration of prairie-style architecture and Wright’s own home and studio.
- Celebrate diversity in a village that prides itself on inclusion across all backgrounds—everyone is truly welcome here.
- Shop the village’s independent boutiques and browse fresh produce and handmade goods at the Saturday farmers’ market.
- Stroll through the Oak Park Conservatory or visit the nearby Brookfield Zoo for a dose of greenery and wildlife.
Distance from Chicago:
Just 25 minutes from downtown by car or CTA Green Line.How to Get to Oak Park:
Take the CTA Green Line westbound toward Harlem/Lake or hop on I-290. Both routes make Oak Park an easy and enriching half-day or full-day trip from the city.7. Six Flags Great America (1 hour)
© Six Flags Great America
Location:
Gurnee, ILHighlights:
Ready for a full day of thrills, laughs, and water park fun just outside Chicago? Six Flags Great America is a must for adrenaline seekers, families, and anyone who loves a mix of roller coasters, rides, and water slides all in one massive park.Recommended For:
Families, teens, thrill-seekers, group outings, summer adventurers, and roller coaster fanatics.What I Love: ♥
The impressive lineup of coasters, the sprawling water park, and the sheer number of options for every age and comfort level—plus plenty of food to keep you fueled up.- Ride one of 17 thrill rides, including 14 roller coasters for every level of daredevil.
- Bring the whole crew—there are 23 family rides and 17 kid-specific rides across the park.
- Cool off at Hurricane Harbor, a 20-acre water park with 30 attractions like surf simulators, lazy rivers, and a massive family pool. Open Memorial Day to Labor Day.
- Refuel with bites from over 50 restaurants and food stands, offering everything from snacks to full meals.
Operating Season:
Late April through early November for the main park; Hurricane Harbor runs Memorial Day through Labor Day.Distance from Chicago:
About 1 hour by car, depending on traffic.How to Get to Six Flags Great America:
Drive north on I-94 toward Gurnee, exit at Grand Avenue, and follow signs to the park. Parking is available onsite, and ride-share drop-off is also an option.Address:
1 Great America Parkway, Gurnee, ILPhone: 847-249-1776
8. North Utica (1 hour 45 minutes)
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Location:
North Utica, ILHighlights:
Need a break from the bustle? North Utica is the kind of charming river town that invites you to slow down, sip local wine, browse antiques, and explore nature just steps from your front porch.Recommended For:
Antique hunters, wine lovers, couples, history buffs, families with kids, and nature-minded travelers seeking a relaxed and scenic retreat.What I Love: ♥
The nostalgic small-town vibes, wine tastings, nearby parks, and that you can do as much—or as little—as you want in one lovely weekend.- Wander into wine shops, antique stores, flea markets, and even a local pottery studio full of rustic charm.
- Learn about the region's roots at the LaSalle County Historical Museum, which covers the town’s rich canal and river history.
- Dine at cozy favorites like Cajun Connection or Canal Port Bar & Grill—both perfect for comfort food after a day of exploring.
- Play with a day pass to Grand Bear Resort’s indoor waterpark, a 24,000-square-foot space with slides, splashes, and treats for all ages.
- Explore four nearby state parks, including popular Starved Rock State Park, known for its canyons, waterfalls, and stunning seasonal hikes.
Distance from Chicago:
About 1.5 hours by car.How to Get to North Utica:
Take I-80 west to Exit 81 (IL-178), then head south into town. The drive is easy and scenic, especially as you approach the Illinois River Valley.Family Day Trips from Chicago:
9. Chicago Botanic Garden (35 minutes)
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Location:
Glencoe, ILHighlights:
Need a breath of fresh air and some serious flower power? Chicago Botanic Garden is an easy escape from the city where nature, design, and tranquility meet across 385 acres of beautifully curated gardens and walking paths.Recommended For:
Garden lovers, families, photographers, birders, nature walkers, and anyone needing a scenic reset just outside Chicago.What I Love: ♥
Over 30 different themed gardens, self-guided audio tours, interactive kid zones, and peaceful spots to sit, stroll, or snap a photo-worthy bloom.- Explore the Crescent Garden, Heritage Garden, and more naturalistic spaces like the Lakeside and Native Plant gardens.
- Take a self-guided walking tour narrated via the garden’s smartphone app—perfect for wandering at your own pace.
- Visit the Nature Play Garden and Children’s Growing Garden for hands-on, outdoor fun with the little ones.
- Try bike rentals or join a birding class for an active garden experience that’s both educational and refreshing.
- Refuel at the onsite restaurant, then stop by the gift shop for nature-themed treasures and garden-inspired gifts.
Distance from Chicago:
Around 30–40 minutes by car or Metra train from downtown.How to Get to Chicago Botanic Garden:
Drive via I-94 to Lake Cook Road or take the Union Pacific North Metra line to Braeside, then walk or bike to the garden. Bike paths connect directly to the entrance!Address:
1000 Lake Cook Road, Glencoe, ILPhone: 847-835-5447
10. Indiana Dunes National Lakeshore (1 hour)
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Location:
Porter, INHighlights:
Craving beach vibes without the flight? Indiana Dunes National Lakeshore offers wild dunes, sandy shores, and skyline views—just a short trip from Chicago.Recommended For:
Beachgoers, nature lovers, hikers, families, photographers, and anyone who wants to see a national park from a towel or trail.What I Love: ♥
The mix of sandy relaxation and rugged adventure, the trails with surprising biodiversity, and the unforgettable view from the top of West Beach’s dunes.- Relax on a 15-mile stretch of pristine Lake Michigan beach—perfect for swimming, sunbathing, or sunset picnics.
- Explore 50 miles of scenic trails for hiking, biking, horseback riding, birdwatching, snowshoeing, and cross-country skiing in the colder months.
- Learn through ranger-led walking tours, or bring the kids to the Nature Play Zone at the Paul H. Douglas Center.
- Step back in time at four historic 19th-century homestead buildings scattered across the park.
- Don’t miss hiking the Succession Trail at West Beach—you’ll be rewarded with a spectacular view of the Chicago skyline from across the lake.
Distance from Chicago:
About 1 hour by car or South Shore Line train.How to Get to Indiana Dunes:
Drive east on I-94 or take the South Shore Line to the Indiana Dunes Station. Free shuttles and local paths connect you to popular beach and trail areas.Address:
1100 N. Mineral Springs Road, Porter, INPhone: 219-395-1882
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