Chicago, Illinois
About chicago
Situated on the shores of Lake Michigan, Chicago, stands as a bustling metropolis celebrated as the cradle of modern architecture. Its skyline, featuring towering icons like the Willis Tower and John Hancock Center, along with the historic Navy Pier—once a naval training site and now a beloved destination for both residents and tourists—tells a vivid visual story. Art and culture lovers can explore many world-class museums and cultural institutions, as well as incredible restaurant and shopping scenes.
Recently Chicago has been home to Sail GP events and World Match Race Tour Events. However, the most famous sailing event in Chicago is the Chicago Yacht Club Race to Mackinac, often referred to simply as “The Mac.” First held in 1898, it is the oldest annual freshwater distance race in the world. This challenging race covers 289 nautical miles from Chicago to Mackinac Island in Michigan.
Getting There
There are two main airports in Chicago, O’Hare International Airport (ORD) and Chicago Midway International Airport (MDW).Both airports utilize public transportation.
You can also rent a car or use a rideshare.
Approximate Travel Times
Local Tips
Sailing Tips
If the wind is out of the west and you’re sailing close to shore, a lot of the puffs are dropping off the buildings and only last 10-15 seconds instead of making their way down the course..
Pizza
While in Chicago, don’t forget to try some iconic Chicago style deep dish pizza! The age- old question of Chicago deep dish vs. NYC thin slice…you be the judge.
Sailing Tips
You’ll usually get wind out of the east or the west. The west is very shifty and puffy and can get very unpredictable if you’re close to shore (i.e. don’t get too leveraged to either side). If it’s out of the east the wind will be very consistent across the course and if it’s heavy wind you get much bigger waves than most people expect for it being a lake.
weather links
SAILING CLUBS
MarinAS/Boat Ramps
Marine Stores
Sails/Rigging
Boat Services
Fuel
Boat Storage
LAUNDRY SERVICES
Grocery stores
hardware stores
RESTAURANTS
Cheesies Pub and Grill is a kitschy casual sandwich shop and pub with a diverse menu of grilled-cheese sandwiches, soups & craft beers. Anything that you can expect with monstrous amounts of cheese, you can get it here! They are open late nights for those after hour cravings, and have a full bar and arcade games as well.
Try local favorite: The Tenderizer- Texas toast filled with cheddar and mozzarella cheese, bacon, fried chicken fingers, and served with a side of ranch dressing. And just imagine their desserts….think apples, and cinnamon, and cheese….
Address: 958 W Belmont Ave. Chicago, IL 60657
Phone: (773)388-1574
Prices: $
Located near the main entrance to Navy Pier, Harry Caray’s boasts an unbeatable waterfront location, out of this world burgers, pizzas, and house smoked barbecue, and a great selection of local craft beer, and a world class collection of sports memorabilia. Harry’s dog friendly patio is an excellent place to enjoy the beauty of Lake Michigan and the hustle and bustle of Navy Pier, and the HDTVs throughout the restaurant and patio bar offer endless access to most major sporting events.
Harry’s boasts an impressive roster of celebrity partners including Patrick Kane, Ryne Sandberg, Richard Dent, and many more of Chicago’s biggest athletes, Hollywood stars, and radio personalities.
Please note that guests of Harry Caray’s are eligible for $20 Navy Pier Valet Parking with validation.
Address: 700 Grand Ave. Chicago, IL 60611
Phone: (312)527-9700
Prices: $$
Located inside the Grand Sheraton Chicago, on the ground level right on the riverwalk, Chicago Burger Company offers some of the juiciest burgers in downtown Chicago, IL. The menu features delicious burgers and hot dogs, vegetarian options, as well as thick shakes and innovative cocktails. Chicago Burger Company is casual and welcoming- you order at the counter and they bring out your food- and offers inside dining in a thriving atmosphere, or outdoor dining right along the river.
Address: 301 E Water St. Chicago, IL 60611
Phone: (312)329-7272
Prices: $$
Located at the Radisson Blu hotel, just steps from Lake Michigan and Millennium Park, Fire Lake Grill is a farm-to-table restaurant that focuses on Midwestern cuisine and specialty cocktails. Known for its wood-fired cooking, Fire Lake Grill offers a menu featuring the Midwest’s best meat, freshwater fish, and produce. Local favorites include the decadent chicken pot pie, and the giant 2 pound Mega pretzel, served with beer cheese and honey mustard. We dare you!
Address: 221 N Columbus Dr. Chicago, IL 60601
Phone: (312)477-0234
Prices: $$$
Labriola Italian is one of Chicago’s best kept secrets for extraordinary authentic Italian food. Known and loved for their award winning brick oven pizza and homemade breads- their breads can be found in stores throughout the Chicago area- Labriola’s is a Chicago staple. They offer a full bar with specialty cocktails and an extensive wine list- and do not miss their Chicago style pizza- just trust us, it takes a solid half hour to make- but is worth the wait! Make sure and try the Gnocchi Bolognese, it is said to be hands down the best in town.
Local Tip: Labriola is a very popular spot located on the Magnificent Mile, so if you don’t see street parking right away, the lot next to Whole Foods is generally a safe bet.
Address: 535 N Michigan Ave, Chicago, IL 60611
Phone: (312)955-3100
Prices: $$
Located right near Millenium Park, Ryo Sushi offers a wide selection of sushi and cooked Japanese specialties. Boasting a menu that focuses on healthy and fresh cuisine- every dish is made from purely natural, raw, local, and sustainable products at Ryo. Known for its incredibly fresh sushi and nigiri, Ryo Sushi is a fresh and modern restaurant with excellent daily specials, as well as take out and delivery options.
Address: 62 E Madison St. Chicago, IL 60602
Phone: (312)409-8888
Prices: $$
SIGHTS
Navy Pier is a 3,300-foot-long pier on the shoreline of Lake Michigan. The pier encompasses over 50 acres of parks (including Polk Bros Park), gardens, shops, restaurants, family attractions, and is one of the top tourist destinations in the Midwest. Opened in 1955, this 50-acre waterfront destination is home to the famous Centennial Wheel, a 200-foot tall ferris wheel, a carousel, Chicago Children’s Museum, and in the summer, numerous firework displays, live music, and theater productions. There are sightseeing cruises available, as well as speedboat tours for the adrenaline junkies.
“The Bean,” officially known as Cloud Gate, is a public sculpture, and the iconic centerpiece of Millennium Park. Created by British artist Anish Kapoor, The Bean is a giant, shiny, and reflective bean-shaped sculpture, famous for its hyper-reflective surface that mirrors the city skyline, as well as ant one near by. The sculpture has become one of Chicago’s most famous public works of art- and in a city filled to the brim with public art- that is saying a lot! The Bean is located on top of Park Grill, between Chase Promenade and McCormick Tribune Plaza and Ice Rink. Believe us when we say, you can’t miss it!
Museum Campus is a 57-acre museum park located on Lake Michigan, right off Lakeshore Drive. The campus surrounds three of the city’s most notable natural science museums: the Adler Planetarium; the Shedd Aquarium; and the Field Museum of Natural History. All three of these attractions are world class institutions and all are well worth a visit. Note that the Field Museum is HUGE and can take quite a bit of time- and if you go, make sure and say hi to Sue, the world-famous T-Rex that stands guard of the institution. It’s worth noting that the park grounds themselves are beautiful and well-maintained, offering lush gardens and walking paths. Museum Campus is an ideal spot for a leisurely stroll and a picnic, and of course some seriously cool natural science opportunities!
Founded in 1879, The Art Institute of Chicago is one of the world’s oldest and largest art museums. Housing an enormous amount of art, including famous artworks such as American Gothic, by Grant Wood, and A Sunday Afternoon on the Island of La Grande Jatte, by Seurat- the Art Institute is filled to the gills with masterpieces. The Institute’s many, many walls hold some of the most well-known and cherished art works in the world- art giants like Hopper, Picasso, Renoir, Cassatt and O’Keeffe are but a few lining the museum’s walls. If you like art of any kind, from any time period, this is THE place to go- do not miss it!
Local Tip: The Museum offers a free, downloadable app that features excellent and informative audio tours.
Chicago is known throughout the world as one of the top architectural giants. Known for its unique and daring architectural pursuits, Chicago boasts some of the world’s inspired buildings. Modern-day skyscrapers meet 100-year-old Art Deco, Neoclassical, and Gothic Towers, throughout the Windy City. There are many ways to experience the architecture throughout town, but one exhilarating and unique way is to tour the spectacular architecture via one of Chicago’s Architecture River Cruises. These cruises focus on the designs, creators, and special innovations behind the city’s world famous architecture, and are an excellent way to kick back and relax while taking in some of the city’s most interesting and intriguing views.