Chicago impresses by day with its architecture and culture, but at night it turns into a center of vibrant entertainment. There is everything here: jazz clubs with history, modern rooftop bars and hidden speakeasy. The city’s atmosphere is often comparable in intensity to the excitement of casinos europeos online — the choice is huge and every night is unique. To make it as interesting as possible, it’s worth planning your itinerary in advance, and below you’ll find tips for a successful evening.
Night city atmosphere
Chicago is one of the largest metropolitan areas in the United States, and it lives a very different rhythm during the day and at night. If during the day it is a business center with skyscrapers, museums and architectural masterpieces, then after sunset the city changes. The streets are filled with the light of neon signs, crowds of fun-loving people, and the sounds of music coming from bars and clubs.
Locals are fond of saying, “If you want to understand Chicago, go out after 10 p.m.”. These are not empty words: this is the time when hidden speakeasies open, jazz clubs fill up, and dance floors rumble.
The atmosphere depends on the neighborhood. River North has a modern, dynamic vibe and is always full of trendy venues. Wicker Park feels like a creative studio, with bartenders experimenting with cocktails and musicians playing in small rooms. Boystown turns every night into a carnival with themed parties, while Lincoln Park and Wrigleyville make it easy to combine a sports game with a bar crawl.
Chicago’s nightlife is a combination of layered culture, history and freedom. And if it’s your first time here, it’s best to make a plan in advance: where to go, what to try and how to have time to see different sides of the city.
Best neighborhoods for a night out
Chicago’s nightlife map is divided into a few key neighborhoods, each of which will suit a different purpose, whether it’s a quiet night at the pub or a clubbing marathon until the wee hours of the morning.
- River North. This neighborhood is called the heart of Chicago nightlife. From chic lounges to dance clubs with world-class DJs, River North is a great place for those who love energetic fun. Many of the venues stay open until the wee hours of the morning, so River North is perfect for those who like energetic fun.
- Division Street. A real center of bar-hopping. The bars are literally one after another, and in the evening the street is closed to cars so that people can move freely from one establishment to another. The atmosphere is festival-like, especially on weekends.
- Wicker Park. A neighborhood for those who appreciate atmosphere and creativity. Here you can find bars with author’s cocktails, art exhibitions and small stages for live music. Often you’ll walk in for one drink and stay all evening because of the unique program.
- Boystown (Lakeview). This place is known as the center of Chicago’s LGBTQ+ culture. It hosts colorful parties, drag shows, and themed events. The neighborhood is friendly and open, and its bars are always filled with positive energy.
- Lincoln Park and Wrigleyville. These neighborhoods are often chosen by students and sports fans. Before a Chicago Cubs game or after a Wrigley Field game, it’s impossible to pass the bars here – the fun literally spills out into the streets. The atmosphere is light, youthful, with plenty of pubs and sports bars.
Each neighborhood gives a different flavor of Chicago at night. To experience the city to the fullest, it’s worth trying a few different routes.
Popular Bar Crawl Routes
If you’re planning a night out with friends and want to have a “bar-crawl” (traveling from bar to bar), Chicago is perfect. There are routes to suit all tastes.
- Historic Jazz Itinerary You can start at the legendary The Green Mill Cocktail Lounge. This club has been around since 1907 and is known as one of Al Capone’s favorite spots. The atmosphere here is like being transported from the past: soft lights, live jazz and bartenders who know hundreds of recipes of classic cocktails. After Green Mill you can go to Old Town Ale House – it’s a more private place with an unusual interior and the spirit of old Chicago.
- Rooftop Bar Tour For those who want to combine drinks and stunning views, the rooftop route is the way to go. Start at Cindy’s, which offers a panorama of Millennium Park and Lake Michigan. Then head up to J. Parker for a great view of Lincoln Park. End the evening at LondonHouse Rooftop Bar, with its multi-level terrace and impressive architecture.
- Cocktail and speakeasy adventures Fans of original drinks should check out The Aviary, one of the most famous cocktail bars in the world. Here drinks are turned into a real show: with smoke, bubbles and unusual serving. For a contrast, you can find the hidden Clandestino in River North – this place is known only to locals and operates as a real ‘secret’ bar.
- Dancing and Live Music If you want to end the night in a club, head to Sound-Bar, a huge room with electronic music and modern lighting. Another option is The Underground, located right under the DuSable Bridge. And for live music lovers, Kingston Mines is an iconic blues club that plays until the wee hours of the morning.
Useful tips for a night out
To make a night out in Chicago as comfortable as possible, there are a few things to keep in mind.
- Transportation. The city is large, so it is better to think in advance how you will move around. Subways and buses run late into the night, but for convenience, many people take cabs or carshare. If you’re going bar-crawling, leave the car at home.
- Rhythm of the evening. To avoid exhaustion, alternate between different venues. Start with a quiet bar where you can socialize, then head to the rooftop for panoramic views, and end the night at a club. This rhythm helps make for a busy but not exhausting night.
- Self-care. Don’t forget to drink water and take breaks. In Chicago, bars often charge a cover charge, so plan your budget.
- Keep up to date. The city’s nightlife is constantly changing, with new bars popping up every season. For example, Friends of Friends in West Town and Pilot Project Brewing in Wrigleyville have been getting attention lately.
- Safety. Chicago is a tourist city, and most neighborhoods popular at night are fairly safe. But as in any metropolis, it’s best to walk in companies and avoid low-lit streets.