Chicago Travel Guide: As Told by A Local

Chicago, also known as the Windy City, is a bustling metropolis located on the shores of Lake Michigan in the midwestern United States. The city is known for its stunning architecture, world-class museums, vibrant music scene, and beautiful lakefront. Chicago is a hub for business and commerce, with many Fortune 500 companies calling it home. The city is also a sports town, with passionate fans cheering on the White Sox, Cubs, Bulls, Red Stars, and Bears. Visitors to Chicago can take a stroll down the Magnificent Mile, visit the Art Institute of Chicago, or take in stunning views from the Willis Tower Skydeck.

I have lived in downtown Chicago for five years, but grew up only an hour north of Chicago and have loved every second of living here. Being the third biggest city, you have so much to do and keep you entertained.

If you are planning to visit Chicago, read more about my guide to make sure your visit to Chicago is as great as possible.

Weather

Chicago experiences distinct seasons, each with its own weather characteristics. Here's a general overview of the weather you can expect in each season:

Spring (March to May): Spring in Chicago is a transitional season characterized by increasing temperatures and occasional rainfall. March can still be chilly, with temperatures gradually warming up as the season progresses. It's advisable to dress in layers during this time.

• Average temperatures: Highs range from the upper 40s°F (8-9°C) in March to the upper 60s°F (17-20°C) in May.

• Precipitation: Spring sees moderate rainfall, so having an umbrella or raincoat is recommended.

Summer (June to August): Summers in Chicago are warm and humid, with occasional heat waves. It's the peak tourist season, and the city comes alive with festivals, outdoor activities, and beachgoers.

• Average temperatures: Highs range from the 70s°F (mid-20s°C) to the mid-80s°F (28-30°C), occasionally reaching into the 90s°F (32°C) during heatwaves.

• Precipitation: Summer can bring occasional thunderstorms, and it's a good idea to carry a light jacket or umbrella for unexpected showers.

Autumn (September to November): Autumn in Chicago brings cooler temperatures and vibrant fall foliage. It's a beautiful time to visit, with pleasant weather and fewer crowds compared to summer.

• Average temperatures: Highs range from the upper 60s°F (17-20°C) in September to the upper 40s°F (8-9°C) in November.

• Precipitation: Autumn sees moderate rainfall, so it's a good idea to have a light jacket or raincoat.

Winter (December to February): Winters in Chicago can be cold, with occasional snowfall. Be prepared for freezing temperatures, and expect winter storms and strong winds.

• Average temperatures: Highs range from the mid-30s°F (1-2°C) in December and January to the upper 30s°F (3-4°C) in February.

• Precipitation: Winter brings snowfall, and heavy snowstorms are not uncommon. It's important to dress warmly with appropriate winter clothing, including hats, gloves, and heavy coats.

Transportation

Chicago's public transportation system is known as the Chicago Transit Authority (CTA). It consists of an extensive network of trains, buses, and a few commuter rail lines. Here's an overview of the different modes of public transportation in Chicago:

• “L" Trains: The "L" (short for "elevated") is Chicago's iconic train system. It operates both above and below ground, serving the city and some suburbs. The train lines are color-coded and named after the destinations they serve, such as the Red Line, Blue Line, and Brown Line. The "L" provides convenient access to major attractions, neighborhoods, and downtown.

• Buses: The CTA operates a comprehensive bus network that covers the entire city, including neighborhoods not served by the "L" trains. Buses run frequently and connect various areas, making it an accessible mode of transportation for getting around Chicago.

• Metra: Metra is a commuter rail system that primarily serves the suburbs of Chicago. It connects downtown Chicago with surrounding areas and offers a convenient option for those living outside the city but commuting downtown for work or other purposes.

• Pace Bus: Pace is the suburban bus system that serves the areas outside of Chicago. It provides transportation to and from the suburbs, as well as connections to the CTA system and Metra stations.

To use the CTA system, you can purchase a reloadable Ventra card, which can be used to pay for rides on both trains and buses. The Ventra card allows you to load funds and passes for unlimited rides within a certain period. You can also use contactless payment methods, such as mobile payment apps or contactless credit/debit cards, to pay for fares.

Chicago's public transportation system is generally efficient, affordable, and a popular choice for both residents and visitors to navigate the city and explore its various attractions.

Neighborhoods

Chicago is a city of diverse neighborhoods, each offering a unique experience. While popular tourist areas are generally safe, it's worth researching specific neighborhoods you plan to visit to understand their characteristics and any specific considerations.

• The Loop: Located in the heart of downtown Chicago, the Loop is the city's central business district. It is home to iconic skyscrapers, including Willis Tower (formerly Sears Tower), as well as cultural institutions like the Art Institute of Chicago and Millennium Park.

• River North: Just north of the Loop, River North is a trendy neighborhood known for its art galleries, upscale restaurants, and vibrant nightlife. It's also home to the Merchandise Mart, one of the largest commercial buildings in the world.

• Lincoln Park: Situated on the North Side, Lincoln Park is a picturesque neighborhood known for its namesake park, which offers lush green spaces, a zoo, and a conservatory. The area is also dotted with charming residential streets, boutiques, and eateries.

• Lakeview: Adjacent to Lincoln Park, Lakeview is a lively neighborhood known for its proximity to Lake Michigan and its vibrant LGBTQ+ community. It's home to Wrigley Field, where the Chicago Cubs play, as well as an array of bars, restaurants, and theaters.

• Wicker Park/Bucktown: Located on the Northwest Side, Wicker Park and Bucktown are hip and eclectic neighborhoods with a mix of trendy boutiques, art galleries, live music venues, and diverse dining options. They're known for their vibrant street art and lively atmosphere.

• West Loop: Once an industrial area, the West Loop has transformed into a trendy neighborhood known for its excellent dining scene, with numerous acclaimed restaurants and celebrity chefs. It's also home to the popular Randolph Street Market for shopping and the United Center, where the Chicago Bulls and Blackhawks play.

• Hyde Park: Situated on the South Side, Hyde Park is home to the University of Chicago and has a rich intellectual and cultural heritage. It boasts beautiful parks, historic architecture, and attractions like the Museum of Science and Industry.

• Pilsen: Pilsen, located on the Lower West Side, is a vibrant neighborhood with a strong Mexican heritage. It's known for its colorful street art, Mexican cuisine, and thriving arts scene, with numerous galleries and art spaces.

• Chinatown: Chicago's Chinatown is a bustling neighborhood on the South Side, offering a vibrant cultural experience. Explore the authentic restaurants, shops, and the iconic Chinatown Gate, and don't miss the annual Chinese New Year celebrations.

• Bronzeville: Bronzeville is a historic neighborhood on the South Side, known for its rich African American heritage and contributions to arts and culture. It was once home to prominent figures like Louis Armstrong and Gwendolyn Brooks, and today it showcases beautiful architecture, jazz clubs, and the DuSable Museum of African American History.

These are just a few of the many neighborhoods in Chicago, each with its own distinct character, attractions, and sense of community. Exploring these diverse neighborhoods is a great way to experience the true essence of the city.

Lake Michigan/ Lakefront

Lake Michigan is a significant feature of Chicago, offering a variety of recreational activities, stunning views, and a beachfront experience. Here's what you should know about Lake Michigan in Chicago:

• Size and Location: Lake Michigan is one of the five Great Lakes of North America and is the only one entirely within the United States. It borders Chicago to the east, providing the city with a picturesque waterfront.

• Beaches: Chicago has several public beaches along the Lake Michigan shoreline. From the popular North Avenue Beach with its iconic beach house to Oak Street Beach and Montrose Beach, these sandy stretches offer opportunities for sunbathing, swimming, beach volleyball, and various water sports during the summer months.

• Lakefront Trail: The Lakefront Trail is a paved path that runs parallel to the Lake Michigan shoreline. It spans approximately 18 miles, offering a scenic route for walking, jogging, cycling, or rollerblading. It's a fantastic way to enjoy the lakefront and take in beautiful views of the city skyline.

• Water Activities: Lake Michigan provides opportunities for various water activities. You can rent kayaks, paddleboards, or jet skis from rental shops along the lakefront. Sailing and boating are also popular options, and boat tours are available to explore the lake and learn about Chicago's history and architecture.

• Fishing: Lake Michigan is known for its diverse fish population, attracting fishing enthusiasts. If you enjoy fishing, you can cast your line from designated fishing areas along the lakefront or join a fishing charter for a deeper lake experience.

• Chicago Air and Water Show: Every summer, Chicago hosts the Chicago Air and Water Show, one of the largest free-air shows in the United States. The event takes place along the lakefront, featuring aerial displays by military and civilian aircraft, as well as water demonstrations.

• Weather and Safety: Lake Michigan's conditions can change, and it's essential to be aware of weather and safety considerations. The lake can have strong currents and undertows, so it's advisable to swim only in designated areas with lifeguards and follow safety guidelines. Pay attention to weather forecasts and any advisories or warnings.

• Sunrise: Lake Michigan offers breathtaking sunrises over the water. You can gather along the lakefront in the mornings to witness the vibrant colors and capture stunning photos.

Lake Michigan is a valuable natural asset for Chicago, providing a beautiful backdrop and recreational opportunities for locals and visitors alike. Whether you want to relax on the beach, enjoy water activities, or simply take a leisurely stroll along the lakefront, Lake Michigan adds to the charm and appeal of the city.

Festivals and Events

Chicago hosts numerous exciting events and festivals throughout the year, showcasing its vibrant culture, diverse communities, and artistic expressions. Here are some of the major annual events and festivals in Chicago:

• Taste of Chicago: Held in Grant Park, Taste of Chicago is one of the city's premier food festivals. It features a vast array of culinary delights from local restaurants, live music performances, cooking demonstrations, and family activities. It typically takes place in July.

• Lollapalooza: Lollapalooza is a world-renowned music festival that brings together top artists from various genres. It takes place in Grant Park over four days, offering a fantastic lineup of live performances, food vendors, and art installations. Lollapalooza usually happens in August.

• Chicago Air and Water Show: As mentioned earlier, the Chicago Air and Water Show is a thrilling event held along the lakefront. It showcases stunning aerial displays by military and civilian aircraft, as well as water demonstrations. The event takes place in August and attracts millions of spectators.

• Chicago Jazz Festival: Celebrating the city's rich jazz heritage, the Chicago Jazz Festival is a free event held in Millennium Park and the Chicago Cultural Center. It features renowned jazz musicians, local talents, and a vibrant atmosphere. The festival typically occurs over Labor Day weekend in September.

• Chicago Blues Festival: Recognized as the largest free blues festival in the world, the Chicago Blues Festival celebrates the genre's roots and its influence on American music. It takes place in Millennium Park and features top blues performers, including both local and international artists. The festival happens in June.

• Chicago Pride Parade: The Chicago Pride Parade is a vibrant celebration of LGBTQ+ pride and diversity. It takes place in the Lakeview neighborhood, with colorful floats, music, dancing, and community participation. The parade typically occurs in June as part of Pride Month.

• Chicago Marathon: The Bank of America Chicago Marathon is a major annual marathon event attracting thousands of participants from around the world. The course takes runners through various neighborhoods, and spectators line the streets to cheer on the participants. The marathon is typically held in October.

• Christkindlmarket: Inspired by the traditional German Christmas markets, the Christkindlmarket is held in Daley Plaza. It offers a festive atmosphere with vendors selling holiday crafts, food, and drinks. The market usually starts in late November and runs through December.

These are just a few examples of the many exciting events and festivals that take place in Chicago throughout the year. The city's calendar is filled with a wide range of cultural, culinary, music, and art events, ensuring there's always something to enjoy and experience in the dynamic city of Chicago.

Chicago’s Food Scene

The food scene in Chicago is renowned and diverse, offering a wide range of culinary experiences. Here's an overview of what you can expect from Chicago's food scene:

• Deep-Dish Pizza: Chicago is famous for its deep-dish pizza, characterized by its thick, buttery crust, generous cheese layer, and chunky tomato sauce on top. Lou Malnati's, Giordano's, Pequod's Pizza, and Gino's East are popular spots to indulge in this iconic Chicago specialty.

• Chicago-Style Hot Dogs: Another beloved local delicacy is the Chicago-style hot dog. It features an all-beef hot dog on a poppy seed bun, topped with yellow mustard, onions, neon green relish, tomatoes, pickles, sport peppers, and a sprinkle of celery salt. Portillo's and Superdawg Drive-In are among the classic hot dog stands to try.

• Italian Beef Sandwiches: Chicago is known for its flavorful Italian beef sandwiches. Thinly sliced seasoned roast beef is piled on a crusty Italian roll and often topped with sweet or hot peppers and dipped in flavorful jus. Al's Beef and Portillo's are famous for their Italian beef sandwiches.

• Ethnic Cuisine: Chicago's food scene is incredibly diverse, with a wealth of ethnic cuisines. From Mexican taquerias in Pilsen to vibrant Indian restaurants on Devon Avenue, you can find flavors from around the world. Explore the neighborhoods like Chinatown, Greektown, and Little Italy for authentic international dining experiences.

• Fine Dining: Chicago boasts a thriving fine dining scene, with numerous Michelin-starred restaurants and acclaimed chefs. Alinea, Grace, and Spiaggia are just a few examples of establishments offering innovative and exquisite culinary experiences.

• Neighborhood Eateries: Chicago's neighborhoods are filled with charming local eateries and hidden gems. From cozy brunch spots to neighborhood taverns serving comfort food, you can discover a wide range of culinary delights throughout the city.

• Food Festivals: Chicago hosts various food festivals throughout the year, such as the Taste of Chicago, Chicago Gourmet, and Veganfest Chicago. These events showcase the city's culinary talents, offering a chance to sample dishes from renowned chefs and local restaurants.

• Craft Beer and Breweries: Chicago has a thriving craft beer scene, with numerous breweries and brewpubs scattered across the city. From Revolution Brewing to Half Acre Beer Company, beer enthusiasts can enjoy a variety of styles and flavors.

• Farm-to-Table and Sustainable Dining: Many Chicago restaurants focus on utilizing local, seasonal ingredients and promoting sustainable practices. These farm-to-table establishments offer fresh, high-quality dishes while supporting local farmers and producers.

• Vegan Food Scene: Chicago is an excellent destination for those who eat vegan or simply are just interested to try a good plant-based eatery. There’s no shortage of good places, but some of my favorites include Planta Queen, Bloom Plant-Based Kitchen, and Kitchen 17.

• Desserts and Sweet Treats: Chicago is not short on sweet indulgences. Don't miss trying the iconic Garrett Popcorn, Eli's Cheesecake, or grabbing a doughnut from Stan's Donuts. The city also offers a plethora of bakeries and dessert shops, satisfying any sweet tooth.

With its blend of iconic dishes, diverse ethnic cuisines, acclaimed fine dining, and a focus on local and sustainable ingredients, Chicago's food scene has something for every palate and budget. Exploring the city's culinary offerings is a delicious adventure that showcases the vibrant gastronomic culture of Chicago.

Areas in Chicago to Stay

The best area to stay in Chicago depends on your preferences, interests, and the purpose of your visit. Here are some popular neighborhoods and areas to consider:

1. Downtown/Loop: Staying in the heart of downtown Chicago puts you close to major attractions like Millennium Park, the Art Institute of Chicago, and the Magnificent Mile shopping district. It's a convenient location with a bustling atmosphere, a wide range of hotels, and excellent transportation connections.

2. River North: Located just north of the Loop, River North is a trendy neighborhood known for its art galleries, nightlife, and dining scene. It offers a variety of boutique hotels, upscale accommodations, and easy access to attractions like the Merchandise Mart and the Magnificent Mile.

3. Magnificent Mile: The Magnificent Mile is a section of North Michigan Avenue known for its luxury shopping, iconic landmarks, and high-end hotels. If you enjoy shopping, being in the midst of luxury brands, and having easy access to famous sights like the John Hancock Center and Navy Pier, this area is ideal.

4. Lincoln Park: Situated on the North Side, Lincoln Park is a charming and picturesque neighborhood with tree-lined streets, historic homes, and the beautiful Lincoln Park itself. It offers a mix of boutique hotels and bed-and-breakfasts, and it's well-suited for those who appreciate a residential feel with proximity to the park and attractions like the Lincoln Park Zoo.

5. Wicker Park/Bucktown: If you prefer a hip and vibrant neighborhood with a lively nightlife, diverse dining options, and unique boutiques, consider staying in Wicker Park or Bucktown on the Northwest Side. This area has a more artistic and alternative vibe, with plenty of accommodation options ranging from boutique hotels to Airbnb rentals.

6. West Loop: Once an industrial area, the West Loop has transformed into a trendy neighborhood with a thriving dining scene, art galleries, and boutique hotels. It's a great choice for food lovers, with numerous acclaimed restaurants and proximity to attractions like Randolph Street Market and Greektown.

7. Near North Side/Gold Coast: The Near North Side and Gold Coast neighborhoods offer a mix of upscale residential areas and luxury hotels. Located just north of downtown, they provide easy access to the Magnificent Mile, Oak Street Beach, and the vibrant nightlife of Rush Street.

Top 20 Things to Do in Chicago for First-Time Visitors

There are countless things to do in Chicago, but here are 20 top attractions and activities to consider:

1. Visit Millennium Park: Explore the iconic Cloud Gate sculpture (a.k.a. "The Bean"), enjoy outdoor concerts at the Jay Pritzker Pavilion, and cool off at the Crown Fountain.

2. Explore the Art Institute of Chicago: Marvel at the extensive collection of artworks, including pieces by Monet, Picasso, and Van Gogh.

3. Take an Architectural Boat Tour: Cruise along the Chicago River to learn about the city's stunning architecture and iconic skyscrapers.

4. Enjoy Navy Pier: Experience the Ferris wheel, ride the carousel, catch a show at the Chicago Shakespeare Theater, and take in the lakefront views.

5. Stroll along the Magnificent Mile: Shop at upscale boutiques, dine at renowned restaurants and admire the stunning architecture along this famous stretch of Michigan Avenue.

6. Explore the Museum Campus: Visit the Field Museum, Shedd Aquarium, and Adler Planetarium, all located within close proximity to each other.

7. Catch a Baseball Game at Wrigley Field or Guaranteed Rate Field: Cheer on the Chicago White Sox or Cubs for an afternoon or evening.

8. Splash around at one of Chicago's many beaches including North Avenue Beach, Oak Street Beach, or Ohio Street Beach.

9. Walk along the Chicago Riverwalk: Enjoy the scenic views, dine at waterfront restaurants, and take part in recreational activities like kayaking or biking.

10. Visit the Lincoln Park Zoo: Explore the free zoo, home to a variety of animals, and relax in the beautiful Lincoln Park surroundings.

11. Experience the Chicago Theatre: Catch a live performance or take a guided tour of this historic and iconic theater in the Loop.

12. Immerse Yourself in History at the Chicago History Museum: Learn about the city's past through engaging exhibits and displays.

13. Enjoy the Chicago Symphony Orchestra: Attend a concert by one of the world's greatest orchestras at the Symphony Center.

14. Indulge in Deep-Dish Pizza: Sample Chicago's famous deep-dish pizza at renowned pizzerias like Lou Malnati's or Giordano's.

15. Wander through the Garfield Park Conservatory: Explore the stunning indoor gardens, tropical exhibits, and beautiful plant collections.

16. Experience the Skydeck at Willis Tower: Step onto the glass floor, known as "The Ledge," for breathtaking views of the city from 1,353 feet above the ground.

17. Attend a live comedy show: Chicago has a vibrant comedy scene, with renowned venues like The Second City and iO Theater offering hilarious improv and sketch comedy performances.

18. Take a Walk on the 606: This elevated park and trail system, formerly a railway line, offers a unique urban green space for walking, biking, and enjoying public art installations.

19. Enjoy the nightlife in Chicago's neighborhoods: From the vibrant bars and clubs in River North to the laid-back pubs in Wicker Park and Logan Square, Chicago offers a diverse nightlife scene to suit various preferences.

20. Enjoy Live Music: Chicago is renowned for its music scene. Catch a live jazz performance at the historic Green Mill, enjoy blues at Kingston Mines, or experience a concert at one of the city's many music venues.

    For the full list of 101 Things To Do in Chicago, click here

Day Trips from Chicago

If you're looking to explore beyond Chicago, here are five fantastic day trip options to consider:

1. Milwaukee, Wisconsin: Located about 90 miles north of Chicago, Milwaukee offers a rich mix of history, culture, and attractions. Visit the Milwaukee Art Museum, explore the Historic Third Ward, sample local breweries, and enjoy the scenic Milwaukee Riverwalk.

2. Starved Rock State Park: Approximately 90 miles southwest of Chicago, Starved Rock State Park is a nature lover's paradise. Hike the park's picturesque trails, admire waterfalls, and explore the stunning canyons carved by the Illinois River.

3. Indiana Dunes National Park: Situated along the southern shore of Lake Michigan, the Indiana Dunes National Park is just a short drive from Chicago. Enjoy sandy beaches, hike through dunes and woodlands, and immerse yourself in the beautiful natural surroundings.

4. Galena, Illinois: Located about 160 miles northwest of Chicago, Galena is a charming historic town known for its well-preserved 19th-century architecture. Explore Main Street lined with boutique shops, visit historic sites, and take a scenic cruise along the Mississippi River.

5. Lake Geneva: Approximately 40 miles west of Chicago, Lake Geneva offers a picturesque escape. Explore the quaint downtown area with its boutique shops and restaurants, go biking or walking along the lake, and enjoy the scenic beauty of the surrounding area.

These day trips provide a mix of natural beauty, historic charm, and nearby cities worth exploring. Whether you're seeking outdoor adventures, cultural experiences, or a change of scenery, these destinations offer great opportunities to enhance your Chicago visit.

Additional Chicago Blogs

101 Things To Do in Chicago: As Told by A Local

Fall in Love with Chicago: The Ultimate Autumn Guide to the Windy City