Monday Night In Chicago: Where To Go Out In 2025

What is it? Boka is a special spot in Chicago, located at 1729 N Halsted St. Here, you'll find modern American food with a creative twist. It's more than just eating; it's a unique experience in a stylish place that grabs your attention.

Why we love it: Boka shines with its lively mood and dishes that both surprise and please. From the moment you walk in, a mix of elegance and warmth welcomes you, preparing you for an unforgettable night. The team's love for top-notch taste is clear in every dish, turning every bite into a memorable moment. It's the perfect place for anyone who wants a bit of luxury in their life.

What is it? Meet Offshore, Navy Pier's crown jewel and the top rooftop bar in the world. It offers amazing views of Lake Michigan and the Chicago skyline, all with a cool, modern feel. Think cozy lounges, trendy fire pits, and a relaxed yet stylish atmosphere. When night falls, live DJs kick the vibe up a notch.

Why we love it: Offshore stands out in Chicago not only because of its size but also due to its unique mix of style and energy. It's the go-to for great drinks, delicious snacks, and incredible views, guaranteeing an unforgettable night. Whether you live in the city or are just visiting, Offshore brings you a mix of chill and thrill, offering a high-flying adventure above the city.

What is it? PRYSM Nightclub on Kingsbury Street is the key to an exciting night in Chicago's nightlife. Picture entering a world where music, lights, and people's energy create an unforgettable time.

Why we love it: It's more than just a night out—it's an adventure. With its modern design and technology, PRYSM pulls you into a show of sounds and visuals. The best DJs play a mix of music that keeps the mood high. Here, everyone is welcome, and the party never stops. PRYSM isn't just a place to visit; it's a place to feel alive.

What is it? Right in the heart of Chicago at 854 W Randolph St, Nobu lights up the scene. It's a perfect mix of new styles and old Japanese charm. As soon as you walk in, calming music sets the stage for an amazing meal. This spot draws in the city's trendsetters and VIPs, all eager for Nobu's famous sushi and unique food.

Why we love it: Nobu Chicago is more than just eating out; it's a full-on adventure. Every plate is a work of art, full of imagination and made with the best ingredients. It's a place where luxury meets creativity, making each meal a feast for your senses.

What is it? Cindy's on 12 S Michigan Avenue is a cool rooftop place. It gives you amazing views of the Chicago skyline and Lake Michigan. This fashionable spot is perfect for a city break.

Why we love it: Cindy's has a great vibe and live music that calms you. It's perfect for a romantic date or hanging out with friends. Locals enjoy it for something different, and visitors get to see what Chicago is all about. Come to Cindy's for an unforgettable time.

What is it? Alinea shines bright in Chicago's busy heart. It's more than eating; it's a journey for all senses, blending innovation with luxury. Alinea's sleek style sets the scene for a night to remember, with music that adds to your food adventure.

Why we love it: It's where food lovers and chefs come together, all drawn by Alinea's bold ideas. The service is top-notch, the food is super creative, and every bite is a new discovery. Here, eating turns into lasting memories, making Alinea not just a meal, but an experience to hold dear.

What is it? Indienne sits in the heart of Chicago. It's a top spot for Indian food, with a cozy, fancy vibe. Here, you get to enjoy rich smells, traditional music, and top-notch service.

Why we love it: Indienne isn't just a restaurant; it's where food lovers meet. Perfect for date nights or catching up with friends, it's always lively and full of great tastes. Whether you know Indian food well or are trying it for the first time, Indienne makes every visit special and tasty.

What is it? Check out VU Rooftop Bar at 133 E Cermak Rd. It's high up and fancy. When night comes, it's full of life. Expect great music, comfy places to chill, and stylish vibes. Here, you can hang out, talk, and enjoy tasty drinks and champagne, all with amazing views of the city.

Why we love it: VU Rooftop Bar is more than just the awesome views. Every visit feels special, no matter why you're there. It's perfect for romantic dates or fun nights with friends. It's the top spot for anyone looking to make their evening a bit more exciting.

What it is: Upstairs at The Gwen is a rooftop spot in Chicago's heart. It's not just any place; it's a cool vibe. You get awesome skyline views that make any night special. There's stylish seating, cool lights, and a modern feel that lifts you above the city buzz.

Why we love it: This place is all about fun times and cool music, with a live DJ that keeps things lively. It's where the trendy crowd hangs out - from city pros to hip young people, all fitting in together with the city lights shining bright. Upstairs at The Gwen is where to be for memorable nights in Chicago's nightlife.

What is it? Z Bar is a stylish rooftop spot in Chicago. It sits high above the city, giving you awesome views. It's cozy and modern, making it a perfect place to unwind.

Why we love it: Z Bar is not just any bar. It brings Chicago to life at night with great music, cool drinks, and a vibrant atmosphere. It's more than just a place to go; it's an adventure. It's where every evening is special, letting you enjoy the city from above. Here, every visit is unforgettable, a real treat for both locals and visitors. Every night is a chance to experience something wonderful.

What is it? LH Rooftop is a cool spot in Chicago, right on the 22nd floor of 85 E Wacker Dr. It mixes awesome city views with style in a great rooftop place.

Why we love it: It's not just the views (and they're amazing) that make us love this place. It's the chill yet fancy feel that pulls you in. With its neat decor and the right music, everything about LH Rooftop feels like a trendy city getaway. It's where the city's energy meets a peaceful break, making each visit special. Whether you're here to relax, chat, or just enjoy Chicago from above, LH Rooftop is where you'll make memories you won't forget.

What is it? Check out Joy District at 112 W Hubbard St, the heart of Chicago nightlife! It's a stylish, buzzing club where the party never ends.

Why we love it: Joy District isn't just a night out; it's an epic adventure. Get lost in the beats from top DJs and live shows, and join a crowd that's all about fun. This place is alive with energy, making each visit unforgettable. Come for the excitement, stay for the amazing memories.

What is it? Aba: A cool rooftop spot on Chicago's 3rd floor at 302 N Green St. Here, you get awesome views of the city, making every visit special.

Why we love it: Aba isn't just any rooftop. It's alive with music that makes you happy, right in the middle of the city's action. It's all about delicious Mediterranean food that's a treat for your taste buds. Perfect for a fun brunch with buddies or a romantic evening under the stars, Aba turns your time into magic. Feel the pulse of Chicago here, making each visit unforgettable.

What is it? TAO Nightclub is the heart of Chicago's fun night scene, located at 632 N Dearborn St. Step inside to find a place where fancy meets fun in a stunning mix.

Why we love it: TAO has an electric feel and a stylish, dimly lit setting that’s not just any place - it’s an adventure. The dance floors light up, pulling you into the night’s beat as top DJs play tunes for everyone. It’s more than a club; it’s where fashion meets fun, making every night special. With a lively crowd, TAO is the top spot in the city for those looking for excitement, music, and memorable moments all in one amazing place.