Top Chicago Attractions for Your Next Visit

Dates of Travel: September 2012, July/August 2013, June 2014, November 2014, March 2018

🔹Favorites: 

-Swissôtel for accommodation: I’ve stayed here in the corner suite most of my trips with views of both the Chicago River and Lake Michigan. It’s right downtown and was convenient for my conference 

Swissotel Chicago – Luxury Hotel In Chicago – SwissĂ´tel Hotels & Resorts

-Kimpton Palomar Hotel (apparently now the Royal Sonesta): Adorable boutique hotel in River North neighborhood. I stayed here the year my conference was in the McCormick Center since I would have to uber there anyway. 

The Royal Sonesta Chicago River North – Official Website

-Architectural boat tour on the Chicago River: I did this two of my first trips and it was so informative and pretty

-Second City Comedy: I went to a show on every visit to Chicago. The best comedy I’ve ever seen. It’s in the Old Town District of Chicago which is also an area I’d recommend

https://www.secondcity.com/shows/chicago

-Sailing on Lake Michigan: On my first trip, friends took us sailing on Lake Michigan and I’d credit this as what made me fall in love

-Seeing the River dyed green for St. Patrick’s day! 

-Cubs games at Wrigley and exploring Wrigleyville 

-The typical spots: Millennium Park, Grant Park, Lincoln Park, Navy Pier, Michigan Avenue

-North Avenue Beach 

-Oak Street Beach 

-West loop neighborhood 

-Gold Coast Neighborhood 

-Restaurants I’ve been to: Eataly, Greektown, Pequod’s Pizza, Kanela for breakfast in Old Town, Eggsperience Cafe, The Dawson, SoHo House, Perennial Verdant 

🔹Photo Gallery:

Map of Chicago highlighting various locations including Wrigley Field, Lincoln Park, and the shoreline along Lake Michigan.

Visual of ground covered 

The Chicago River dyed green for St. Patrick's Day, featuring nearby historic buildings and a cloudy sky.

Riverfront on St. Patrick’s Day

Chicago River dyed green for St. Patrick's Day, with city buildings in the background.

Riverfront on St. Patrick’s Day

Chicago River dyed green for St. Patrick's Day, with skyscrapers in the background and a boat on the water.

Riverfront on St. Patrick’s Day

View of the Chicago River dyed green for St. Patrick's Day, featuring downtown buildings and a bridge in the foreground.

Riverfront on St. Patrick’s Day

View of the Chicago River dyed green for St. Patrick's Day, with the Wells Street bridge and skyscrapers in the background.
Chicago skyline featuring a mix of modern and historic buildings along the river, with clear blue skies.

Riverfront on St. Patrick’s Day

Fireworks display over Lake Michigan with illuminated buildings and attractions along the riverfront at night.

Fireworks over Navy Pier from our friends’ condo in Streeterville

Person smiling while sitting on a boat at night.

Sailing on Lake Michigan 

Night view of Chicago skyline with illuminated buildings along the waterfront.

Skyline from Lake Michigan 

View of Chicago skyline at night from a sailboat on Lake Michigan.

Sailing on Lake Michigan 

Person smiling in front of a city skyline, wearing sunglasses and casual clothing, with high-rise buildings and a clear sky in the background.

Rooftop views 

View of Wrigley Field with a scoreboard and crowds during a baseball game.

Wrigley!

A blurry selfie of a woman smiling, wearing a baseball cap, in a crowded indoor setting.
View of Wrigley Field during a baseball game with fans in the stands, scoreboards visible in the background.
Street view near Wrigley Field with pedestrians and vehicles, featuring directional signs and flags.
Facade of a historic red brick building with decorative architectural elements and trees in the foreground.

Walking around Wrigleyville

View of the Chicago River with skyscrapers in the background, including a raised bridge, during sunset.

Chicago River

View of the Chicago River with illuminated skyscrapers and a bridge opening at sunset.
Night view of the Chicago River and skyline, showcasing buildings illuminated by city lights against a dusky sky.

View from SwissĂ´tel

View of Chicago skyline and Lake Michigan at sunset, with tall buildings lining the riverfront.

View from SwissĂ´tel

View of Chicago skyline with buildings and Lake Michigan in the background

Friend’s condo in Gold Coast

View of a marina with several sailboats on calm waters, under a clear blue sky, with the Chicago skyline in the background.

Shoreline Trail

View of a rainy Chicago night from a hotel window, featuring illuminated buildings and city streets.

Rainy view from the SwissĂ´tel

Two women posing for a fun selfie in a dimly lit venue.

Night out in Boystown 

View of a bridge over the Chicago River with skyscrapers in the background during twilight.
Blurred view of the illuminated Navy Pier entrance sign at dusk.
View of the Chicago Riverwalk with modern buildings in the background at dusk.
Brightly lit Ferris wheel at Navy Pier against a twilight sky, capturing the festive atmosphere of the amusement area.

Navy Pier 

Chicago skyline at dusk with reflections on the water.

Evening run on the lakeshore trail

Chicago skyline at dusk, with illuminated buildings reflecting on the water and a clear sky above.
Silhouette of the Chicago skyline at sunset, viewed from the waterfront.
Individual smiling in sunglasses in a park setting with architectural structures in the background.
A pathway lined with tall flower planters, featuring colorful blooms, under a blue sky with clouds, and a person jogging in the distance.

Maggie Daley Park

A reflection of people walking near a large sculpture with a smooth, curved surface, set against a blue sky with scattered clouds.

The Bean 

Reflective surface of the Bean sculpture in Millennium Park with city skyscrapers and a cloudy sky in the background.
Reflection of Chicago's skyline and clouds in the surface of the Cloud Gate sculpture, commonly known as 'The Bean'.
Reflection of Chicago skyline in the Cloud Gate sculpture, with two people in the foreground.
Reflection of the Chicago skyline and clouds in the Bean sculpture at Millennium Park
Group of people enjoying an architectural boat tour on the Chicago River, with city buildings in the background.

Architectural tour

View of a historic building in Chicago with a clock tower against a clear blue sky.
Chicago skyline featuring tall modern buildings and a clear blue sky
View of Marina City towers in Chicago against a clear blue sky, showcasing distinctive round balconies and nearby skyscrapers.
Sky view of historic skyscrapers in Chicago with a clear blue sky.
View of modern skyscrapers with reflective glass facades in downtown Chicago under a blue sky.

SwissĂ´tel from the River

View of Oak Street Beach with city buildings in the background on a sunny day.

Gold Coast

Night view of the Chicago skyline with illuminated buildings and clouds in the sky.

Skyline view from our friends’ condo in Streeterville

Night view of the Chicago skyline with numerous illuminated buildings and a cloudy sky.

Skyline view from our friends’ condo in Streeterville

Nighttime skyline view of Chicago, featuring illuminated skyscrapers and city lights.

Skyline view from our friends’ condo in Streeterville

Nighttime skyline view of Chicago showcasing illuminated buildings and streets.

Skyline view from our friends’ condo in Streeterville

Sidewalk view of the Chicago Theater with a Walgreens nearby, surrounded by tall buildings.
View of the Chicago River with a boat passing under a bridge, surrounded by skyscrapers and greenery.
Entrance archway to Old Town neighborhood in Chicago with nearby storefronts and flower pots.
Exterior view of a comedy club with a marquee displaying event details and surrounded by greenery.

Second City— The Best Comedy!

Exterior view of the Old Town Ale House with a sidewalk and a passerby in casual attire.

Old Town Ale House, where all the comedians convene 

View of the Chicago skyline from a park, surrounded by lush greenery and blooming flowers on a sunny day.

Lincoln Park

View of the Chicago skyline from Lake Michigan on a clear day, with the water shimmering in the foreground.

Skyline from Gold Coast

Foggy view of Oak Street Beach with high-rise buildings partially obscured in the background, featuring beach-goers walking along the shore.

Gold Coast

Two women wearing red ponchos smiling in a cosmetics store aisle.

Caught in a rainstorm after Eataly on the way to the Cubs game

Scenic view of Lake Michigan with sailboats and a walking path, featuring a person with a dog and the Chicago skyline in the background.

Lakeshore Trail

A view of the Chicago River with skyscrapers in the background and a rainbow created by a fountain, showcasing a vibrant urban landscape.

View from SwissĂ´tel

A serene park scene featuring a statue surrounded by lush green trees and a wet stone pathway, hinting at recent rain.

Millennium Park 

Sculptures of human figures in a public park with trees and people walking in the background.

Millennium Park 

Statue of a horseman in a park with cloudy skies and traffic lights in the background.

Grant Park 

View of the Clarence Buckingham Memorial Fountain in Grant Park, Chicago, with water fountains and a cloudy sky.

Clarence Buckingham Memorial Fountain 

Silhouette of a statue on a hill with urban skyscrapers in the background

Grant Park

A lush green pathway lined with trees and buildings in the background, taken in a park-like setting, with a cloudy sky.

Grant Park 

A statue of a female figure holding a torch, set against a cloudy sky, with greenery and historical architecture in the background.

Grant Park

View of the Bean sculpture in Millennium Park, Chicago, with nearby outdoor dining areas and high-rise buildings in the background under a cloudy sky.

Millennium Park

Chicago River with historical buildings and a police boat, viewed on a cloudy day.

St. Patrick’s day ceremony 

View of the Chicago waterfront with a boat and Ferris wheel on a clear day

Navy Pier view from the Lakefront Trail

View of a lake with a monument featuring a statue on horseback in the background, surrounded by trees under a blue sky.

Lincoln Park

Statue of Abraham Lincoln standing on a stone pedestal, surrounded by leafless trees against a blue sky

Lincoln Park 

Flamingos resting near a pond surrounded by tall grasses and buildings in the background at Lincoln Park Zoo.

Flamingos at the Lincoln Park Zoo 

Group of camels resting near a log in a zoo setting.

Camels at the Zoo 

View of the Chicago skyline from a park with a river in the foreground and a curved structure in the center.

Lincoln Park Zoo 

Statue of a mounted figure on a stone pedestal surrounded by bare trees and blue sky.

Lincoln Park Zoo 

Pathway through a park with bare trees, leading to a skyline view of Chicago on a clear day.

Lincoln Park Zoo 

A tranquil view of a sandy beach with calm water and a clear blue sky, featuring wooden posts along the water's edge.

North Avenue Beach 

View of the Chicago skyline from Lake Michigan on a sunny day, with blue skies and shimmering water.

North Avenue Beach 

View of the Chicago skyline from North Avenue Beach with sandy beach in the foreground and a clear blue sky.

North Avenue Beach 

View of Lake Michigan with marinas and a tree in the foreground on a clear day.

North Avenue Beach 

Sailboats on Lake Michigan with a clear blue sky in the background.

North Avenue Beach 

View of a calm marina with empty docks and clear blue water on a sunny day.

North Avenue Beach 

Exterior view of Pequod's Pizza sign on a sunny day with a parked car-lined street

Pequods Pizza 

🔹GPS Tracks:

Map displaying a walking route through Lincoln Park in Chicago, showing distance and time.
Map showing a running route along Lake Michigan in Chicago, marked with a distance of 3.73 miles and total time of 45:49.

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