Discover Chicago, Illinois

Traveling to Chicago promises an exhilarating journey into the heart of the Midwest, where vibrant culture, iconic architecture, and culinary delights await. As you arrive, the majestic skyline, punctuated by towering skyscrapers and the shimmering waters of Lake Michigan, welcomes you to the Windy City. Whether exploring world-class museums like the Art Institute of Chicago, indulging in deep-dish pizza at renowned pizzerias, or strolling along the picturesque Riverwalk, there’s no shortage of experiences to captivate visitors.

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Fun Facts About Chicago

01

The Windy City

Chicago is famously known as “The Windy City,” not because of its weather (although it can be windy!), but because of its long history of political hot air and debates.

02

The Great Chicago Fire

The Great Chicago Fire of 1871 destroyed much of the city, but it also led to a remarkable period of rebuilding and growth. The city’s architecture flourished in the aftermath, resulting in the birth of the modern skyscraper.

03

The Bean

Cloud Gate, affectionately known as “The Bean,” is a popular public sculpture in Millennium Park. Designed by artist Anish Kapoor, its mirrored surface reflects the city skyline and has become a beloved symbol of Chicago.

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Must See Attractions

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Brookfield Zoo

Zoo

This acclaimed zoo is just a train ride away and a must-visit! Imagine wandering among some of the most wondrous animals from around the globe. Add it to your itinerary for a refreshing escape from the city’s bustle.

Chicago Botanic Garden

Nature & Parks

Ready for a breath of fresh air? The Botanic Garden boasts 23 gardens, serene waterfalls, and a rich tapestry of native prairies. It’s perfect for a calming day trip to reconnect with nature.

Art Institute of Chicago

Speciality Museums

Explore one of the oldest and largest art museums in the United States, featuring a vast collection of artworks from around the world.

Navy Pier

Shopping & Attraction

Spend a day at this bustling entertainment complex along Lake Michigan, featuring shops, restaurants, boat cruises, the Chicago Children’s Museum, the Centennial Wheel, and seasonal events like fireworks.

Architecture River Cruise

Attraction

Take a guided boat tour along the Chicago River to admire the city’s stunning architecture, including iconic buildings like the Willis Tower, Tribune Tower, and Wrigley Building.

Magnificent Mile

Shopping

Shop ’til you drop on this famous stretch of Michigan Avenue, known for its upscale boutiques, department stores, restaurants, and architectural landmarks.

Lakes Near Chicago

Lake Michigan

Chicago, Illinois

Just east of the Loop, Chicago’s downtown, Lake Michigan offers a refreshing escape. Facing its glistening blue waters, it’s hard not to feel the stress melt away. The lake’s shores are perfect for a stroll or a lively bike ride.

Distance from Chicago: One mile
Activities:
Boating, swimming, fishing, kayaking

Chain O’Lakes

Spring Grove, Illinois

Situated in northern Illinois, the Chain O’Lakes is a chain of interconnected lakes and waterways that offer excellent boating, fishing, and water sports opportunities. With over 7,000 acres of water and 488 miles of shoreline, it is one of the largest inland recreational waterway systems in the United States.

Distance from Chicago: 55 miles
Activities:
Boating, fishing, water sports

Lake Geneva

201 Wrigley Drive, Lake Geneva, Wisconsin

Lake Geneva is a popular getaway destination for Chicagoans in Wisconsin, just over the Illinois border. This picturesque lake offers boating, fishing, kayaking, and lakeside dining opportunities. The charming town of Lake Geneva also features boutiques, restaurants, and historic estates along its shores.

Distance from Chicago: 83 miles
Activities
: Boating, fishing, kayaking, lakeside dining

Fishing Destinations Near Chicago

Lake Michigan

Chicago, Illinois

First up, Lake Michigan is your go-to for that urban fishing escape. You’re in luck if you want to land some trout or maybe a salmon! Along the shores of Chicago, Lake Michigan offers you the city skyline and fishing opportunities. Imagine that—skyscrapers and fishing rods!

Fishing: Boat, shoreline, harbors
Species: Salmon, walleye, perch, small and largemouth bass

Lake Springfield

Springfield Lake Shore Improvement, Illinois

If you’re in the mood for a weekend getaway, why not drive to Lake Springfield? It’s about a three to four ride from downtown Chicago, but the trip is worth it. You’ve got 3,866 acres of fishing grounds—we’re talking a hefty dose of bass, catfish, and more. Get your playlist ready, and hit the road for some lakeside serenity!

Fishing: Boat, kayak, shoreline 
Species: Bass, catfish, bluegill, crappie

Lake Catherine

Lake Catherine, Illinois

Situated near Chain O’Lakes State Park in Antioch, Lake Catherine is often overlooked but provides fantastic fishing for largemouth bass, bluegill, and northern pike. It’s a serene spot with fewer crowds than other nearby lakes.

Fishing: Shoreline
Species: Bluegill, crappie, catfish, pike

Top Hiking Trails One Hour From Chicago

Lincoln Park Trail

1730 N Stockton Dr, Chicago, Illinois

Not far at all, you’ve got the Lincoln Park Trail. It’s a classic, and guess what? You can grab a coffee at a local bar before hitting the trail. This urban adventure is perfect for a quick escape while staying close to city comforts.

Distance: Five miles
Type: Loop
Difficulty:
Easy
Elevation Gain: 26 m
Time to Complete: 1.5 hours

Skokie Lagoons Inner Trail

N Branch Trail System – Black Paved Lp, Glencoe, Illinois

Skokie Lagoons Inner Trail offers a serene escape into nature outside Chicago’s bustling urban landscape. Situated within the Skokie Lagoons Forest Preserve in Glencoe, Illinois, this scenic trail winds through lush woodlands, tranquil wetlands, and peaceful lagoons. Spanning approximately 4.5 miles, the trail provides an ideal setting for hiking, jogging, birdwatching, and nature photography.

Distance: 4.1 miles
Type: Loop
Difficulty: Easy
Elevation Gain: 17 m
Time to Complete: 1.5 hours

Waterfall Glen Trail

Waterfall Glen Main Trail, Darien, Illinois

Fancy something a bit more secluded? Check out the Waterfall Glen Forest Preserve. With its beautiful cascades and ample trails, it’s a haven that’s practically next door. It’s ideal when you’re short on time but need a full dose of nature.

Distance: 9.3 miles
Type: Loop
Difficulty: Moderate
Elevation Gain: 122 m
Time to Complete: 3.5 hours

Best Golf Courses Around Chicago

Chicago Golf Club

25W253 Warrenville Rd, Wheaton, Illinois

Chicago Golf Club holds a revered place in the annals of golf history as one of the oldest and most prestigious golf clubs in the United States. Founded in 1892, this historic club is located in Wheaton, Illinois, a suburb west of Chicago. Renowned for its classic design and championship-caliber course, Chicago Golf Club has hosted numerous prestigious events, including the U.S. Open and the Walker Cup.

Holes: 18
Designer: C.B. Macdonald

Wild Rock Golf Club

856 Canyon Rd, Wisconsin Dells, Wisconsin

Wild Rock Golf Club, nestled in the picturesque Wisconsin Dells, offers golfers a unique and exhilarating experience. With its dramatic rock formations, rolling fairways, and meticulously manicured greens, Wild Rock presents golfers with a scenic and challenging round amidst the beauty of the Wisconsin countryside. The course’s layout incorporates the natural terrain and showcases strategic bunkering and water features, providing an engaging test for players of all skill levels.

Holes: 18
Designer: Michael Hurdzan

Sydney R. Marovitz Course

3701 N Recreation Dr, Chicago, Illinois

Sydney R. Marovitz Course, located along the picturesque shores of Lake Michigan in Chicago, offers golfers a unique and scenic urban golfing experience. This 9-hole, par-36 course, nestled within the bustling Lakeview neighborhood, provides stunning views of the city skyline and the tranquil waters of Lake Michigan.

Holes: 9
Designer: Edward B. Dearie Jr., Harry Bowers

Tips on Renting a Vacation Property in Chicago

Research Neighborhoods

Chicago is a city of diverse neighborhoods, each with its unique character and attractions. Research different areas to find one that suits your preferences regarding location, ambiance, and attraction convenience.

Set a Budget

Determine your budget for accommodation and consider factors such as the property size, amenities offered, and proximity to key attractions.

Book in Advance

Popular vacation rentals in Chicago tend to book quickly, especially during peak seasons like summer and major events. Even if you plan an off-season trip, such as visiting one of the fall fairs in Illinois, but still call Chicago home base, you’ll want to secure your rental well in advance to avoid missing out on your preferred property.

Have a Backup Plan

While rare, unexpected issues can arise with vacation rentals. Have a backup plan in case of emergencies or last-minute changes to ensure a stress-free trip.

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Frequently Asked Questions about Chicago

Looking for luxury? Sites like Lake and Airbnb are treasure chests that offer splendid options, from guest suites in hip neighborhoods like Andersonville to chic apartments downtown. Don’t forget to compare with listings on Hometogo for exclusive deals!

You bet! Downtown Chicago is peppered with vacation rentals that put you in the heartbeat of the city. Whether you prefer the buzzing streets or a tranquil spot with a view, you’ll find a rental that suits your urban adventure.

Bagging a bargain can be as simple as booking during the off-peak times or scouring for new listings that may offer introductory rates. Keep an eye on price drops—you might just land a sweet spot at a not-so-steep price!

You may not need to play detective here, but it’s good to know Chicago has regulations in place for vacation rentals. Ensure that the property you’re eyeing is licensed to avoid hiccups during your Chi-town escapade.

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