Windy City Waterfront: Top Ways to Soak Up Chicago’s Scenic Lake Michigan Shoreline

Post originally Published December 29, 2023 || Last Updated December 30, 2023

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Windy City Waterfront: Top Ways to Soak Up Chicago's Scenic Lake Michigan Shoreline - The Lakefront Trail - Chicago's Scenic Green Ribbon


Windy City Waterfront: Top Ways to Soak Up Chicago’s Scenic Lake Michigan Shoreline

Stretching for 18 miles along the shores of Lake Michigan, the Lakefront Trail is Chicago’s scenic green ribbon of paths for walking, running, cycling, and simply taking in the splendid views. This trail connects an array of Chicago’s top attractions, making it easy to explore many of the city’s highlights on two wheels or two feet.

On any given day, you’ll find the trail bustling with joggers, rollerbladers, cyclists, and families out for a relaxing stroll. Locals and visitors alike flock to the Lakefront Trail to soak up the fresh lakeside breezes and take in vistas of Chicago’s striking skyline and the vast blue expanse of Lake Michigan. Early risers can catch golden sunrise views across the water, while late afternoon brings stunning sunsets over the Chicago cityscape.
In addition to the marvelous scenery, the trail winds past numerous attractions and landmarks. Going from north to south, the trail connects gems like Lincoln Park, North Avenue Beach, Navy Pier, the Museum Campus, Soldier Field and McCormick Place. There are also plenty of spots to stop for a picnic, go for a swim, or grab a drink or a bite to eat along the way.

For many Chicagoans, no summer is complete without multiple trips on the Lakefront Trail. Locals cherish early morning jogs along the path, family bike rides on sunny weekends, and leisurely strolls to take in the lake views. It offers an easy escape from the hustle and bustle of downtown into a scenic landscape that feels worlds away.
Visitors adore the Lakefront Trail as an easy and inexpensive way to experience Chicago’s famous lakefront. It offers a front row seat to many of the city’s top sights without the hassle of driving or public transport. Travelers say it’s one of the best ways to get a quintessential taste of Chicago in just a few hours of walking or cycling.

What else is in this post?

  1. Windy City Waterfront: Top Ways to Soak Up Chicago's Scenic Lake Michigan Shoreline - The Lakefront Trail - Chicago's Scenic Green Ribbon
  2. Windy City Waterfront: Top Ways to Soak Up Chicago's Scenic Lake Michigan Shoreline - North Avenue Beach - A Prime Spot for Sun & Fun
  3. Windy City Waterfront: Top Ways to Soak Up Chicago's Scenic Lake Michigan Shoreline - Navy Pier - Iconic Chicago Landmark on the Lake
  4. Windy City Waterfront: Top Ways to Soak Up Chicago's Scenic Lake Michigan Shoreline - Museum Campus - Art & Nature Along the Water
  5. Windy City Waterfront: Top Ways to Soak Up Chicago's Scenic Lake Michigan Shoreline - Harbor Tour Boats - Cruising Chicago's Magnificent Lakefront
  6. Windy City Waterfront: Top Ways to Soak Up Chicago's Scenic Lake Michigan Shoreline - Kayaking & Paddleboarding - Get Out on the Water
  7. Windy City Waterfront: Top Ways to Soak Up Chicago's Scenic Lake Michigan Shoreline - Alfresco Dining with a View - Lakefront Restaurants & Cafes
  8. Windy City Waterfront: Top Ways to Soak Up Chicago's Scenic Lake Michigan Shoreline - Sunset Strolls & Lakefront Paths - Evening Ambles by the Water

Windy City Waterfront: Top Ways to Soak Up Chicago's Scenic Lake Michigan Shoreline - North Avenue Beach - A Prime Spot for Sun & Fun


Known for its lively atmosphere and stunning city views, North Avenue Beach is one of Chicago’s most popular lakefront escapes. This beach has everything visitors love about Chicago’s summers – plenty of sun, sand, water fun, and that friendly Midwestern vibe.

Stretching for a mile along the lakefront, North Avenue Beach is conveniently located just north of the Gold Coast and Lincoln Park neighborhoods. It’s usually buzzing with activity thanks to the plethora of amenities, from volleyball nets and stand up paddleboard rentals, to snack bars and beachfront restaurants.
North Avenue Beach draws a festive mix of families, friends, runners and sunbathers. You’ll see kids building sandcastles, teens playing beach volleyball, and young professionals soaking up some rays after work. There’s always a game of beach soccer, volleyball or frisbee happening, not to mention swimmers and stand up paddleboarders gliding across the calm blue waters.
The lively beach scene is anchored by the iconic North Avenue Beach House. This Art Deco building houses DJ booths, a gym, bike rentals, a bar and grill, and the iconic rooftop patio. Grab a burger or beer while gazing at the Chicago skyline - it doesn't get much more quintessentially Chicago than this.

Nearby you’ll also find the North Avenue pier, which makes a lovely spot to stroll out over the water for unobstructed panoramas of the cityscape. It’s especially stunning at dusk, when the buildings light up as the sun dips towards the horizon.

When you need a break from the sand and surf, take a scenic stroll south towards the historic Navy Pier, or head north to the tranquil gardens of Lincoln Park. The Lakefront Trail connects North Avenue Beach to all of Chicago's top lakefront hotspots.

Windy City Waterfront: Top Ways to Soak Up Chicago's Scenic Lake Michigan Shoreline - Navy Pier - Iconic Chicago Landmark on the Lake


Jutting nearly 3,000 feet into Lake Michigan, Navy Pier stands as one of Chicago’s most iconic and beloved landmarks. Locals and visitors alike are drawn to this bustling pier for its wealth of dining, shopping and entertainment options, all packed into a scenic setting on the shimmering blue lake.

Originally built in 1916 as a shipping and recreational pier, Navy Pier was temporarily converted to a military training center during World Wars I and II. After falling into disrepair for several decades, the pier underwent extensive renovations in the 1990s and reemerged as Chicago’s top lakefront attraction.

Today, Navy Pier hums with activity year-round and ranks as the Midwest’s top tourist draw. The pier stretches half a mile and covers more than 50 acres of space filled with restaurants, shops, gardens, concert venues and amusements. Visitors adore strolling the length of the pier to soak up panoramic views of Chicago’s skyline while enjoying lakefront breezes.
One Navy Pier highlight is the iconic Centennial Wheel. This enormous Ferris wheel carries visitors nearly 200 feet in the air for unbeatable vistas across Lake Michigan and back towards Chicago’s glittering towers. The wheel’s twinkling lights create a magical scene after dark.

For many, no trip to Navy Pier is complete without a cruise aboard one of the sightseeing boats. Options range from architecture tours along the Chicago River to private chartered cruises on Lake Michigan. Gliding across the water offers an idyllic perspective of the city’s world-famous architecture.

Navy Pier also houses the Chicago Children’s Museum, perfect for families looking to entertain the kids. Visitors of all ages flock to Amazing Chicago’s Funhouse Maze and the Crystal Gardens botanical center with its lush palms and cascading fountains.

When it’s time to refuel, Navy Pier offers over 50 restaurants ranging from deep dish pizza to fine dining. Grab famous Garrett’s popcorn, chow down on Chicago-style hot dogs or indulge in upscale fare with waterfront views. Many restaurants boast outdoor patios perfect for dining al fresco in summer.

Windy City Waterfront: Top Ways to Soak Up Chicago's Scenic Lake Michigan Shoreline - Museum Campus - Art & Nature Along the Water


Sprawling across 57 acres of prized lakefront real estate, Chicago’s Museum Campus delivers a delightful fusion of art, nature and architecture. Located just south of downtown, this campus unites three world-class museums in a setting that artfully blends manicured greenspace and sweeping lake vistas.

The Museum Campus stars the Field Museum of Natural History, Shedd Aquarium and Adler Planetarium, conveniently connected by the scenic Lakefront Trail. This pedestrian path makes it easy to explore all three institutions during a single visit. Or spend a whole day diving into the fascinating exhibits at just one.
Nature lovers, science buffs and families flock to the Museum Campus to admire rare aquatic life, dinosaurs, Egyptian mummies, and much more. But beyond the cultural riches within the museums, the campus itself imparts a deep appreciation for the natural splendor surrounding Chicago.
Strolling from museum to museum, visitors soak up panoramic views of Lake Michigan and Chicago's striking skyline. Lush, green lawns ideal for picnicking sprawl towards the Adler Planetarium. A scenic promenade leads out to the 12th Street Beach, where many take a refreshing dip in the lake after hours of enriching museum exploration.

The neoclassical grandeur of these lakefront museums combined with the serene natural setting makes the campus a joy to experience. As one TripAdvisor user described, "it is a little oasis right in the middle of the city."

Within the soaring halls of the Field Museum, globetrotting families find endless fascination. Kids gape in awe at the largest and most complete T-Rex fossil ever found, dubbed “Sue.” Mythic gems like the cursed Hope Diamond or an ancient Egyptian sarcophagus tempt visitors to linger for hours uncovering mysterious tales.
The Field Museum’s trove of cultural artifacts vividly illustrates human civilizations across eras and continents. For many visitors, it’s a journey across the world without ever leaving Chicago. As one visitor raved, “from dinosaurs to rare gems to Egyptian mummies, every section is so interesting!”

Just steps away, the otherworldly Shedd Aquarium showcases an incredible diversity of aquatic life. At the fascinating Polar Play Zone, kids can pop up inside a faux seal den and imagine life as these adorable Arctic creatures. Everyone delights at the playful antics of belugas and whales gliding past the floor-to-ceiling glass walls.

The most mesmerizing exhibit is the color-changing jellyfish drifting like alien creatures through their luminous tanks. As one recent visitor described, “the jellyfish are so gorgeous, I could stare at them for hours!"

Capping off the campus, the Adler Planetarium launches visitors on an odyssey through the cosmos. In the state-of-the-art Grainger Sky Theater, the Galactic Starshow hurls viewers lightyears away to witness the miracles of deep space unfold.

The Adler perfectly caters to curious young astronomers. Kids can climb inside a module of the International Space Station, touch a real moon rock and sit atop a Mercury capsule. A dad who recently visited with his 7-year-old son shared, “the space museum was my boy’s dream come true!"

Windy City Waterfront: Top Ways to Soak Up Chicago's Scenic Lake Michigan Shoreline - Harbor Tour Boats - Cruising Chicago's Magnificent Lakefront


Gliding across the shimmering blue expanse of Lake Michigan, Chicago's harbor tour boats offer a blissful perspective of the city's world-famous architecture and breathtaking waterfront. From intimate charters to sightseeing cruises for hundreds, tourists adore hitting the lake for closeup views of Chicago's towers and scenic shoreline.
For many visitors, a boat tour ranks as the highlight of their Windy City getaway. As one TripAdvisor user remarked, "the architecture tour was the best way to see Chicago - so much beautiful history from the water!" Others rave about the joy of sitting back with a drink in hand to soak up the sights without the stress of driving or finding parking downtown.

Several companies offer narrated tours that weave along the main branch of the Chicago River through the heart of downtown. Listen as knowledgeable guides delve into the illustrious past behind buildings like the Wrigley Building, Tribune Tower, and the Chicago Board of Trade. You'll gain insight into legendary architects like Mies van der Rohe and Louis Sullivan who shaped Chicago's architectural legacy. Gliding gently down the river, passengers snap photos of iconic structures like Marina City's corncob towers and the Art Deco gems of the Loop.

For unobstructed vistas of the Chicago cityscape, many opt for a lake cruise. Leaving behind the curtain of skyscrapers, the boat heads out onto Lake Michigan's open waters. Passengers are treated to panoramic views of Navy Pier, Ohio Street Beach, and Chicago's gleaming walls of glass. As the boat curves back towards shore, the Chicago skyline rises majestically like a mountain range of steel and stone. A passenger who took the 90-minute Skyline Lake Cruise described it as "the most amazing way to take in the Chicago skyscrapers!"

Several companies also offer private charters, perfect for popping the question, celebrating an anniversary or simply an intimate escape for two. One glowing 5-star review read "the private boat tour made for the most romantic Chicago date night!"

For families, kids adore getting out on the water away from the crowds. Many tour operators offer special cruises where kids can serve as the captain steering the boat or go on a scavenger hunt to spot local wildlife along the shore. Amom who booked a family cruise shared, "it was wonderful to see the joy in our kids' faces as they experienced the magic of Chicago by water."

Windy City Waterfront: Top Ways to Soak Up Chicago's Scenic Lake Michigan Shoreline - Kayaking & Paddleboarding - Get Out on the Water


For an invigorating perspective of Chicago's waterfront, adventurous travelers are increasingly flocking to kayaking and stand up paddleboarding. Gliding across the calm waters of Lake Michigan, it's a peaceful way to soak up the sights at your own pace.

Kayaking has exploded in popularity, with convenient kayak rentals available all along Chicago's beaches. As avid kayaker Mark raves, "paddling the lake is an awesome core workout without feeling like exercise at all - just pure fun!"

It's the perfect activity for outdoorsy couples looking to get their hearts pumping together. Friends appreciate having time to chat while taking in lake views without the sweat and crowds of cycling or running the lakefront trail. Families with kids love embarking on mini-adventures while teaching young ones skills and respect for the water.
Most kayak rental outlets offer single or tandem options so you can cruise solo or share the experience with a friend or loved one. Costs typically run $15-20 per hour.
Paddleboard yoga has also emerged as a trendy wellness activity. Gliding through yoga poses on the water intensifies the challenge, while the sensation of floating atop the lake creates a deeply calming effect.

Anna did paddleboard yoga during a recent Chicago vacation and said, "floating while stretching intensified the core workout so much - I was sore for days after! But breathing in that fresh lake air while looking up at the skyscrapers was totally zen."

Kathy, a 50-year-old newcomer to SUP, admits she was nervous at first but got the hang of it quickly. "Within 15 minutes I felt steady and comfortable paddling - it's such an intuitive way to explore the lake."

The brilliant blue waters of Lake Michigan make an ideal paddleboarding playground. Most days the lake surface stays calm, allowing SUP fans to stride and glide for hours taking in gorgeous views.

When asked about stand up paddleboarding Chicago's lakefront, young adventure guide Will explained, "on a nice summer day when the water's smooth, you can easily go for 5 or even 10 miles if you have the stamina. And the scenery of the Chicago skyline keeps getting better and better!"

Windy City Waterfront: Top Ways to Soak Up Chicago's Scenic Lake Michigan Shoreline - Alfresco Dining with a View - Lakefront Restaurants & Cafes


After hours spent soaking up Chicago’s scenic lakefront sights, nothing caps off the day better than alfresco dining with a view. Luckily, Chicago’s magnificent waterfront boasts no shortage of restaurants and cafes with patios primed for panoramic vistas.

Visitors rave about kicking back on Navy Pier for perfect people-watching, sunset views and dining just steps from world-class attractions. Grab authentic deep dish pizza at Giordano’s on the pier’s outer edge, where every bite comes with stunning skyline views. Or splurge on upscale Italian at Offshore Rooftop & Bar’s alfresco terrace - their Aperol spritz and lobster bucatini pair swimmingly with the glittering cityscape.

Closer to the pier’s entrance, Harry Caray’s Tavern even boasts an outdoor beer garden for sampling local brews and grub from this Chicago icon under the open skies. As regular Bobby J. says, “Soaking up the atmosphere on the pier with a cold Goose Island and hot dog just feels so quintessentially Chicago, I love it!”

For glittering skyline vistas further south, Aeon Lounge’s chic patio spreads along historic Buckingham Fountain. Sipping signature cocktails and nibbling Asian fusion tapas as the fountain’s light show illuminates, you’ll feel worlds away from the bustling Loop just blocks away.

Travelers say Aeon Lounge offers “the best outdoor date night ambience,” and their heat lamps keep the patio pleasant even on brisk evenings. The bean-shaped seating makes it perfect for sipping with your sweetie while reminiscing about architectural gems like the Tribune Tower.

Families flock a bit further south to the Lakefront Trail’s newest food gem, Upside Down Pops for what Beth H. dubbed “the ultimate kids-eat-free meal with a view!” This trailer turned brick-and-mortar café crafts heavenly gourmet popsicles with globally inspired recipes, from mango lassi or Mexican hot chocolate to sneaky veggie combos like beet-carrot-apple. With indoor and outdoor seating right on the lakeside trail, Upside Down Pops lets parents savor lake breezes and skyline views while kiddos delight in popsicle bliss. A mom named Annie said, “it was the yummiest and most scenic family snack break along Chicago’s stunning lakefront!”

Windy City Waterfront: Top Ways to Soak Up Chicago's Scenic Lake Michigan Shoreline - Sunset Strolls & Lakefront Paths - Evening Ambles by the Water


After a day packed with Chicago’s top attractions, many travelers find that sunset brings the perfect chance to decompress with a leisurely lakefront stroll. The city’s scenic paths winding along Lake Michigan are ideal for evening ambles that immerse you in natural tranquility with unbeatable skyline views.

Making your way south from attractions like Navy Pier or the Museum Campus, the lakefront trail leads onward, ever quieter and more serene as dusk approaches. Joggers and cyclists gradually fade away as families pack up their picnics and couples head off to dinner. Soon you find yourself nearly alone, enveloped in the gentle lapping of waves.

This is Chicagoans’ favorite time for donning jackets on cooler evenings to soak up Lake Michigan’s tranquility. As lifelong Chicagoan Janice explains, “An evening walk along the lakefront trail is my stress-relieving ritual after busy workdays. Listening to the waves, gazing at the glittering skyline, it restores my spirit.”

Others agree that Lakeshore paths make for delightfully romantic reunions at day’s end. Michael recently planned a surprise visit to his long-distance partner in Chicago and says their evening lakeside stroll stands out as the weekend’s most magical memory. “Walking hand-in-hand at sunset, the summer breeze rustling through the trees, it felt like we were the only two people in the world.”

Indeed, Chicago’s lakefront trails seem to cast everyday worries adrift as the sky dims to dusk. You forget busy highways and bustling streets for a while, fully present and at peace.

As the sun dips towards the horizon, the Chicago skyline begins illuminating in a dazzling display. Because the lakefront paths sit slightly elevated, you’re treated to postcard views as lights wink on inside the iconic towers.

Visitors lucky enough to be strolling by on clear evenings are awestruck by Chicago’s sunset magic. “It was like seeing two different but equally beautiful cities – the sunlit daytime Chicago, then this glittering nighttime spectacle,” raved Maya after her first lakeside evening amble.

Locals who walk the lakefront trails daily never tire of this sunset skyline spectacle. There are gasps of delight as the buildings begin glowing amber, then vibrant reds and purples reflected on the glass walls from the sinking sun.

couples, families, tourists all stand shoulder to shoulder in hushed reverence as the sun sinks below the horizon. Then the buildings shine forth like sons to light up the urban night until it’s time for another magnificent Chicago sunrise.
As Kathy, who’s lived her whole life in Chicago, effuses: “Hustle and bustle can make you forget the simple magic of a sunset. But here along Chicago’s magnificent lakefront, it’s impossible not to stand in awe.”

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