Chicago Uncovered: A Traveler’s Guide to the Windy City

Discover Chicago

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. Whether you’re a first-time visitor or a seasoned explorer, Chicago’s boundless energy and endless possibilities ensure an unforgettable journey filled with discovery and delight.


Best time to visit
Best places to visit

Fun Facts About Chicago


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.


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.


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.


Must See Attractions

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Brookfield Zoo


Just a train ride away, this acclaimed zoo is a must-visit! Imagine wandering among some of the most wondrous animals from around the globe. You can 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


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


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

Have you ever dreamed about lounging by a serene lake, yet found yourself right in the heart of the bustling Windy City? Well, you’re in luck! Lake Michigan is not just a stone’s throw away, it’s your enormous, freshwater neighbor right alongside Chicago’s eastern edge. Isn’t it fascinating to think that you have one of the largest lakes in the world as your next-door pal?

Lake Michigan

S Lake Michigan Dr. Empire, Michigan 49630

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, don’t you agree? The lake’s shores are perfect for a leisurely stroll or a lively bike ride. Spot any avid joggers or relaxed picnic-goers lately? They’re probably reveling in the scenic beauty that the lakeside effortlessly provides.

Distance from Chicago: 1 mile
Boating, swimming, fishing, kayaking

Chain O’Lakes

8916 Wilmot Road Spring Grove Illinois 60081

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, the Chain O’Lakes is one of the largest inland recreational waterway systems in the United States.

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

Lake Geneva

201 Wrigley Drive, Lake Geneva, Wisconsin 53147

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

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

Fishing Destinations Near Chicago

Hey there! Are you itching to cast a line without venturing too far from the Windy City? Let’s talk about some prime fishing spots where you can reel in a big one without a big journey. Your fishing tales are just waiting to be made. So grab that tackle box, get out there, and make some waves with your rod and reel. Whether you choose the urban backdrop of Lake Michigan or a serene excursion to Lake Springfield, your perfect catch is waiting. Happy fishing!

Lake Michigan

S Lake Michigan Dr. Empire, Michigan 49630

First up, Lake Michigan is your go-to for that urban fishing escape. If you’re looking to land some trout or maybe a salmon, you’re in luck! Along the shores of Chicago, Lake Michigan offers you both 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 take a drive to Lake Springfield? It’s about a 3 to 4-hour 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, saugeye, bluegill, crappie

Lake Catherine

Lake Catherine, Illinois 60002

Situated near the 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 compared to other nearby lakes.

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

Top Hiking Trails 1 Hour From Chicago

Hey there, outdoor enthusiast! Looking to trade the Windy City skylines for some natural vistas? Lucky for you, there’s a slice of scenic wonder just an hour away from Chicago. Let’s lace up those hiking boots and venture into the wild! So, ready to escape the hustle and bustle of the city? Nature’s calling and it’s just around the corner. Happy trails to you!

Lincoln Park Trail

1730 N Stockton Dr, Chicago, Illinois 60614

Not far at all, you’ve got the Lincoln Park Trail. It’s a classic favorite 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: 5 miles
Type: Loop
Elevation Gain: 26 m
Time to Complete: 1.5 hours

Skokie Lagoons Inner Trail

N Branch Trail System – Black Paved Lp, Glencoe, Illinois 60022

Skokie Lagoons Inner Trail offers a serene escape into nature just outside of Chicago’s bustling urban landscape. Situated within the Skokie Lagoons Forest Preserve in Glencoe, Illinois, this scenic trail winds its way 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 60561

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 for 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

Hey there, golf aficionado! Are you looking to tee off in the Chicago area? There’s an amazing selection of courses where you can practice your swing and enjoy the beauty of the landscapes. Remember, each course comes with its unique charm and challenges. Whether you’re here for the weekend or you call Chicago home, you’re bound to find a course that fits your style. So grab your clubs, and let’s hit the green!

Chicago Golf Club

25W253 Warrenville Rd, Wheaton, Illinois 60189

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

Visit their website for more information

Wild Rock Golf Club

856 Canyon Rd, Wisconsin Dells, Wisconsin 53965

Wild Rock Golf Club, nestled in the picturesque Wisconsin Dells, offers golfers a truly 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

Visit their website for more information

Sydney R. Marovitz Course

3701 N Recreation Dr, Chicago, Illinois 60613

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

Visit their website for more information

Tips on Renting a Vacation Property in Chicago

Research Neighborhoods

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

Set a Budget

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

Book in Advance

Popular vacation rentals in Chicago tend to book up quickly, especially during peak seasons like summer and major events. 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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Jet Skiing

Ready to find that perfect Chicago vacation rental? Let’s jump right into the nitty-gritty so you can book with confidence.

Finding the Right Spot

Location, location, location! You’re looking for convenience, right? Whether that’s being close to Millennium Park or steps away from deep-dish pizza, here’s what to consider:

– Proximity to attractions
– Access to public transportation

Types of Rentals

Chicago offers a smorgasbord of properties. From studio apartments for solo adventures to spacious houses and condos for the whole crew.

Must-Have Amenities

WiFi: For sharing your snaps or if you’re remote working.
A kitchen: Who doesn’t love a homemade breakfast?
Luggage storage: Drop those bags and explore.
Parking: Free parking is a gem in the city.

Entertainment and Comfort

– Look for listings with Netflix after a long day of exploring.
– A lovely bathroom can be a game-changer!

Pets and Pricing

Bringing a furry friend? Pet-friendly options are a must. As for the average price, it varies—but you can snag a sweet deal with a little digging.

Before You Book

– Check guest reviews and photos.
– Ask about check-in/out times and if they can accommodate early/late requests.

By keeping these tips in mind, you’ll be well on your way to booking a vacation rental in Chicago that ticks all the boxes. Just imagine the memories you’ll make! Happy hunting!

Going Deeper

Ready to soak in the bustling city vibes with a side of comfy, just-like-home living? Chicago awaits, with its dynamic blend of urban sophistication and Midwestern charm! With a rich variety of vacation rentals, ranging from modern apartments in The Loop to cozy townhomes in Logan Square, you’re spoiled for choice. Who wouldn’t love their own space to kick back after a day exploring the Windy City?

Imagine sipping your morning coffee with views of Lake Michigan or unwinding in a chic loft in River North after chasing sunsets on the Chicago Riverwalk. Here’s a tempting bit: over 9,000 property options cover you, with tasteful apartments making up 63.93% of available accommodations. On average, you can snag a rental for $310 a night, and with spaces averaging 84m², there’s room to bring your friends or family for a memorable city getaway.

Heading out? The Loop and Downtown Chicago offer heart-pumping excitement where skyscrapers reach for the clouds, and the urban pulse never skips a beat. If foodie adventures call your name, West Loop’s culinary scene is a treasure trove of delights. More of a night owl? Wicker Park and Old Town serve up vibrant nightlife that keeps the city humming until dawn.

And hey, don’t fret over the weather in Chicago. You’ve got a warm and cozy rental waiting after a dreamy snow day or a sunny urban adventure. Hyde Park offers peaceful retreats near the University of Chicago’s gothic architecture, whereas Lakeview teems with youthful energy. Whether you’re in town for business near O’Hare or on a family vacation, Chicago’s neighborhoods cater to every vibe and occasion.

Check out this quick list of bustling ‘hoods:

Gold Coast & Near North Side: Upscale living and luxury shopping
Uptown: Historic venues and global cuisine
Avondale: Quirky and artsy locales for the adventurous soul
West Town: Industrial-chic streets lined with galleries and boutiques
Irving Park: A quiet community feel for a relaxing stay

Which one’s calling your name? Book your Chicago vacation rental, and get ready for an urban adventure that feels just like home.

Now, if you’re thinking about overnight stays, consider the variety of lake rentals available in and around Chicago. Imagine waking up to the sound of waves gently lapping at the shore, right from the comfort of your Lake rental. You might find a cozy spot with its own heated pool or a charming rustic cabin with a fire pit to warm up those breezy nights.

While you’re enjoying the maritime vibes, you might stumble upon some fantastic lake house getaways. They could range from a penthouse with all the trimmings—think fireplaces and balconies—to quaint cottages just a short drive into Wisconsin.

So, next time you’re looking for an urban adventure with a touch of tranquility, you know where to set your sights. How’s tomorrow looking for a visit to beautiful Lake Michigan?

Chicago and Lake Michigan

Hey, did you know that Lake Michigan is not just a lake, but a freshwater giant that shapes the entire personality of Chicago? It’s true! Let’s explore some quick, cool tidbits about this legendary body of water and its surrounding cityscape.

Chicago’s endearing nickname, “The Windy City,” isn’t just about the breeze off the lake—nope! While Lake Michigan definitely contributes to the city’s gusts, the term was originally coined to describe Chicago’s talkative politicians. Go figure, right? Still, the lake’s winds are nothing to scoff at; they’re a big part of what makes the city so vibrant.

Lake Michigan
– Size: 5th largest lake in the world
– Role: Major influence on Chicago’s climate

So next time you’re strolling along the lakefront or exploring Chicago’s grand avenues, remember these little nuggets of knowledge and impress your travel buddies with your insider info!

Frequently Asked Questions about Chicago

Looking for luxury? Sites like Lake and Airbnb are a treasure chest, offering 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!

Absolutely! Many rentals, especially those listed on platforms like Rent By Owner™, offer the flexibility for longer-term stays. This adaptability makes it perfect for those extended vacations or business trips.

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.

Fido can come too! Search filters on sites like Lake, Airbnb, and Rent By Owner™ make sniffing out pet-friendly listings as easy as a walk in the park. Some even offer special amenities to make your pet’s stay as comfy as yours.

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. Always ensure that the property you’re eyeing is licensed to avoid any hiccups during your Chi-town escapade.

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