A First-Timer's Adventure in Chicago

Sites

Chicago is filled with a vibrant network of public spaces that highlight different parts of the city. Walk along the river to enjoy cafes and public art installations, spend time in to Millennium Park, home to Cloud Gate colloquially known as "The Bean," or get out onto Lake Michigan on Navy Pier.

Navy Pier

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Navy Pier is a major Chicago attraction on the waters of Lake Michigan. You can roam around on the pier and experience the shops, restaurants, museums, and live shows. If you're looking for a great view, ride the Centennial Wheel to get a glimpse of the Chicago skyline. Sunday – Thursday 11:00 am – 9:00 pm Friday – Saturday 11:00 am – 10:00pm *Hours may vary per establishment and in Pier Park The pier is free to visit but tickets are required for many of the museums and attractions. You can buy different types of ticket bundles on their website.

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Riverwalk

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The Chicago Riverwalk is a 1.25 mile long park that runs along the river. You can stroll along the scenic path and enjoy waterfront eateries, architectural gems and bridges, and open spaces for relaxing by the water. Free public park open year-round, businesses will vary in operating hours

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Cloud Gate

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Cloud Gate, also known as "The Bean," is a large public sculpture iconic to Chicago. Located in Millennium Park, it is created from polished stainless steel plates, its smooth, mirror-like surface reflecting you and the city's skyline. Free public park open year-round, sometimes the park restricts access when at capacity

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Lurie Garden

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Lurie Garden, located in Millennium Park, is nature escape from the urban downtown. The garden is made up of a dynamic mix of perennials, bulbs, grasses, shrubs, and trees designed by landscape architects. Free public park open year-round

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Maggie Daley Park

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Sitting between Millennium Park and Lake Michigan, Maggie Delay Park is a park filled with family-friendly activities. Their large Play Garden has a variety of spaces for kids of varying ages. Throughout the garden you'll also find a climbing wall, mini-golf, and ice-skating (depending on the season). Free public park 6:00 am to 10:00 pm

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Clarence F. Buckingham Memorial Fountain

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Located in the center of Grant Park, the Buckingham Fountain is a landmark and popular tourist destination. The design of the fountain was inspired by the Latona Fountain at Versailles. The central jet shoots 150 feet into the sky and at night the water moves with music and lights. Free public park open year-round

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Tour Recommendation 

If you're interested in taking a walk tour through these sites while enjoying Chicago bites, this tour would be great for you! Walk through iconic Chicago sites with a guide telling you about the history and architecture of the spaces. You'll end the tour with lunch in the River North neighborhood to try Chicago food highlights like the Chicago dog, deep dish pizza, and the Italian beef sandwich.

Chicago in a Day: Food, History and Architecture Walking Tour

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Iconic Buildings

Chicago is home to many iconic buildings creating the fabric of the city. Several of the city's sky scrapers are architectural marvels with details making each one of them unique. The Willis Tower, once the world's tallest building, offers panoramic views, while the Chicago Cultural Center features free exhibitions and events that celebrate the city's rich artistic heritage.

Chicago Cultural Center

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The Chicago Cultural Center is an iconic building in the heart of The Loop right across from Millennium Park. You can walk through the building to enjoy the stunning architecture and see mosaic patterns and stain-glassed domes. They host art exhibitions, events, and performances, all free for the public to enjoy. Daily, 10am-5pm Exhibition galleries begin closing 15 minutes prior to building closing. Tickets are not required for entry into the building or exhibitions. Admission is free.

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The Chicago Theatre

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“The Chicago Theatre was the first large, lavish movie palace in America and was the prototype for all others.” It is an iconic landmark in the city’s fabric, referenced in multiple movies. You can visit for a tour or buy tickets to watch a live performance. Tours Friday-Saturday, 12PM and 2PM $20

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Skydeck Chicago

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Skydeck Chicago is an observation deck on the 103rd floor of Willis Tower. The Ledge, a glass box that pops out from the face of the building, lets you see Chicago literally under your feet. March – September Sunday – Saturday 9:00am – 10:00pm October – February Sunday – Friday 9:00am – 8:00pm Saturday 9:00am – 9:00pm Tickets start at $30

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TILT @ 360 Chicago

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Located on the 94th floor on the former John Hancock Tower, 360 Chicago is an observation deck that gives you a panoramic view of the city and Lake Michigan. Their main attraction is Tilt, a thrill ride that brings you floating over the city. They also have a bar so you can grab a drink while you enjoy the view. 9am-11pm Daily Last entry 1 hour prior to closing General admission $30 Tilt and view $39

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Tour Recommendation

If you're interested in learning more about the city's architecture and the history behind these iconic buildings, take a river cruise hosted by the Chicago Architecture Center. You'll cruise down the Chicago River on Chicago's First Lady with a tour guide to explain it all. Sit on the upper deck to get a clear view of the buildings, but bring a jacket in the colder months for the wind chill.

Chicago Architecture Center River Cruise aboard Chicago's First Lady

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Museums

Chicago has many museums for you to explore. Immerse yourself in impressionist masterpieces at The Art Institute of Chicago, journey through natural history at the Field Museum, or experience the wonders of science and technology at the Museum of Science and Industry.

The Art Institute of Chicago

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One of the best art museums in the country, the Art Institute of Chicago houses the largest collection of impressionist art outside the Louvre. They have a variety of rotating exhibitions and give free tours daily. Some of the well known works include “A Sunday on La Grande Jatte” by Seurat, “Water Lilies” by Monet, and “Self-Portrait” by Van Gogh. Mon 11–5 Tue–Wed Closed Thu 11–8 Fri–Sun 11–5 General Admission $32

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Adler Planetarium

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Alder Planetarium was the first planetarium in the western hemisphere and continues to be a leader in science education. They host a variety of theater programs, exhibitions, and events that encourage the exploration of the universe. Thursday-Tuesday 9AM-4PM Wednesday 4PM-10PM Tickets start at $25

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Shedd Aquarium

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The Shedd Aquarium is a great place to get up and close to over 30,000 different sea species. Their exhibits include the Abbott Oceanarium where you'll find beluga whales and sea otters, and the Polar Play Zone perfect for kids to touch starfish and see penguins. The building is currently being upgraded with most experiences to be completely by summer 2024. Hours vary day to day, typically opening at 9 or 10am and closing at 6pm or 10pm Tickets are available 2 months in advance and vary based on expected attendance, around $40

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Field Museum

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The Field Museum is Chicago's natural history museum. It is home to Máximo the Titanosaur, one of the largest dinosaurs discovered. If you're interested in history from China to Egypt to the Ancient Americas, they have the exhibits for you. Open daily, 9am-5pm, last entry 4pm General Admission $30

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Museum of Ice Cream

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The Museum of Ice Cream is the perfect spot to unleash your inner child. They have interactive installations for you to explore, play, and take photos. Your ticket includes unlimited ice cream, but if you're looking for something with more a of kick they also have a speakeasy serving sweet cocktails! Sun-Thur 10AM-7PM Fri-Sat 10AM-730PM WEEKDAY TICKETS From $25 WEEKEND TICKETS From $33

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WNDR Museum

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The WNDR (Wonder) Museum is an immersive art museum filled with interactive exhibits to spark your curiosity. One of the most popular installations is Chicago’s first-ever Infinity Mirror Room by Japanese artist Yayoi Kusama. Walking through each exhibit will take you on journey through different spaces of art, light, and sound. Monday-Thursday 12pm - 8pm Friday-Saturday 10am - 8pm Sunday 10am - 6pm General Admission starts at $32

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Garfield Park Conservatory

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Garfield Park Conservatory is one of the largest botanical conservatories, also known as “landscape art under glass.” They have indoor gardens highlighting palms, ferns, and aroids. Their outdoor city garden has a large lily pool for the public to enjoy. Wednesday 10am-8pm (last entry at 7:15pm) Thursday – Sunday 10am-5pm (last entry at 4:15pm) Closed Monday and Tuesday Admission is free and requires reservations.

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Museum of Science and Industry, Chicago

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The Museum of Science and Industry is one of the largest science museums in the world. It is filled with exhibits exploring tornados and sand storms, a German submarine, and a mirror maze. There will be plenty for you to explore! Regular Hours daily from 9:30 a.m. to 4 p.m. Summer Hours through August 18, 2024: Open 9:30 a.m. to 5:30 p.m. Tickets start at $26

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Chicago CityPASS

Depending on which museums you're interested in, the Chicago CityPASS might be right for you. In one pass you get tickets to  the Shedd Aquarium and Skydeck Chicago, as well as admission to 3 additional attractions of your choice.

Chicago CityPASS®

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Food

Chicago has many quintessential eats from their deep dish pizza to the Chicago-style hot dog, the Italian beef sandwich to the Garrett's popcorn on every corner. Even beyond the staples, the city is home to many top chefs creating their mark on the Chicago food scene. You'll find many Michelin-starred restaurants to fill any appetite.

Chicago Classics

Garrett Popcorn Shops

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Since 1949, Garrett's Popcorn Shops have been specializing in small-batch, gourmet popcorn, popping fresh flavors throughout the day. They are most known for the Garrett Mix, a blend of their signature CaramelCrisp and CheeseCorn recipes making a sweet and salty treat. Garrett Popcorn Shops are not only a fun snack, but also a popular souvenir. No reservations Sun–Thu 10 AM–8 PM Fri–Sat 10 AM–9 PM $

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Portillo's Hot Dogs

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Portillo's is a local favorite and fast-casual joint known for their Chicago-style hot dog, topped with all the classic like sport peppers, juicy tomatoes, and neon green relish. They are also popular for their Italian Beef sandwich and char-grilled burgers. One of their well known desserts is the chocolate cake milkshake, made with a slice of their legendary chocolate cake. No reservations Monday-Friday: 10:00 am - 10:30 pm Saturday: 10:00 am - 12:00 am (midnight) Sunday: 10:00 am - 10:30 pm $

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Al's #1 Italian Beef

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Al's Italian Beef is a local legend, serving up iconic Italian beef sandwiches since 1938. They are most known for their slow-roasted Italian roast beef, thinly sliced and piled high on a toasted Italian roll. You can customize it "wet" dipped in gravy, "dry" with just a drizzle, or "dipped" for a happy medium. No reservations MONDAY - SATURDAY 10:30AM-12:00AM SUNDAY 10:30AM-9:00PM $

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Manny's Cafeteria & Delicatessen

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Manny's Cafeteria & Delicatessen has been a Chicago institution since 1942. They are a cafeteria-style eatery famous for Jewish comfort food like corned beef sandwiches, latkes with applesauce, and matzo ball soup. It has been a popular spot for politicians and celebrities, with the walls adorned with photos of famous patrons. No reservations Sunday 8am - 3:30pm Monday 8am - 3:30pm Tuesday - Saturday 8am - 7:30pm $$

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River North - Lou Malnati's Pizzeria

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Lou Malnati's is one of the oldest family names in Chicago pizza. If you're looking for the classic, deep dish pizza with a flaky, buttery crust, chunky tomato sauce, and fresh mozzarella cheese, this is the place to visit. They are an iconic pizzeria, where the recipe has been passed down generation to generation. Takes reservations Mon-Thu 11am-11pm Fri-Sat 11am-12am Sun 11am-11pm $$

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Pequod's Pizza

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Although not technically a deep dish pizza, Pequod’s still stands in the top ranks of Chicago favorites. They are most famous for their caramelized crust - a dark ring of crispy cheese around the edge of their pie. Reservations are highly recommended so that you can ensure you get a seat at this crowded sports bar. Online reservations Monday – Saturday: 11am – 2am Sunday: 11am – 12am $$

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Chicago Favorites

The Purple Pig Restaurant

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The Purple Pig is a Mediterranean tapas restaurants perfect for a group dinner. Some of their highlights include roasted bone marrow, crispy pigs ear, and the lamb shank. You can wash everything down with their craft cocktails or finish your meal with their tiramisu. Reservations recommended, walk-ins accepted. Sunday - Wednesday: 11:00am-9:00pm Thursday - Saturday: 11:00am-10:00pm $$

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Girl & The Goat

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A well-known spot, Girl & the Goat by Chef Stephanie Izard is serving new American food in both their Chicago and Los Angeles locations. On the menu you'll find variations on it's namesake, goat, in forms like empanadas or mousse. The rest of the menu is divided into bread, veggies, fish, and meats perfect for sharing plates with friends. Reservations highly encouraged to reduce wait time, but walk-ins are accepted Sunday - Thursday 4:30pm - 10pm Friday & Saturday 4:30pm - 11pm $$$

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Monteverde Restaurant & Pastificio

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Monteverde is an Italian restaurant in the West Loop by Top Chef Sarah Grueneberg. It is a Chicago favorite for special occasions serving house-made pasta and large plates like ragu alla napoletana. If you can't get in for dinner, they have lunch and aperitivo hour. Dinner reservations are booked months in advance. TUE-TH 11:00am-9:30pm FRI-SAT 11:00am-10:30pm TUESDAY - SATURDAY APERTIVO HOUR 2:30pm-4:30pm Closed Sunday and Monday $$$

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Kasama

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Kasama, a personal favorite, is the only Filipino restaurant in the world with a Michelin star. They serve breakfast and baked goods by day and transform into a fine dining tasting menu at night. During breakfast they have classics like Filipino breakfast, adobo, and many bakery items. Their dinner tasting menu has a more modern take with lamb belly kare-kare or squab inasal. Asian-owned; reservations are for dinner only and release on a 45 day rolling calendar. They can be a little tough to get, but if you put the work in, it’ll be worth it. Walk-ins only for breakfast, but you'll need to get there very early to avoid standing in line for too long! Daytime Wednesday – Sunday 9am – 3pm Dinner Service Thursday – Sunday Reservation Only $$$

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Tortello

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The large window at the front of Tortello will draw you in as you watch them create their hand-made pastas. Walk inside to the counter to order your food and you'll see even more trays of pasta and options for you to take home! On their menu you'll find tortelli stuffed with burrata, tagliatelle with a beef ragu, or duck parpardelle, you can't go wrong when the pasta is this fresh. No reservations M 4:30PM – 9PM T — TH 11:30AM – 9PM F — SU 8AM – 9PM $$

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Taqueria Chingon

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A Chicago favorite for tacos! At Taqueria Chingon you order at the counter then wait in the outdoor patio for your tacos served on a freshly made tortilla. Their menu varies from classics like al pastor to more atypical offerings like duck carnitas or blood sausage. Follow their instagram to see their daily specials or their next 'tacomakase' event. No reservations Tuesday- Saturday 11:00am - 9:00pm Sunday 11:00am-8:00pm Closed Mondays $

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Lardon

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Lardon is an old-world inspired salumeria focused on utilizing every part of the animal. They highlight their house-cured meats in their charcuterie boards, pairing them with artisan cheeses and wines. If you're looking for something a little more filling, they are open for breakfast, lunch, and dinner with varying menus. At lunch, you'll find the ruben, rumored to be the best pastrami in the city! Reservations online MONDAY-THURSDAY | 8 AM - 9 PM FRIDAY-SATURDAY | 8 AM - 10 PM SUNDAY | 8 AM - 4 PM $$

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Lula Cafe

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Lula Cafe is the neighborhood spot in Logan Square good for brunch, lunch, and dinner. Their menu is locally sourced and rotates seasonally, with favorites such as the "Royale" Breakfast Sandwich for brunch or Baked French Feta for dinner. They also offer a 6 course vegetarian tasting menu and on Mondays they host farm dinners (three new courses for $46). Reservations for dinner only; walk in for brunch and lunch, but come early or expect a line! 9:00 AM - 3:00 PM 4:30 PM - 10:00 PM WEDNESDAY - MONDAY CLOSED TUESDAYS $$

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Food Halls

Revival Food Hall

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Revival Food Hall in the heart of The Loop is focused on highlighting Chicago locals. You have Danke, from the same team behind Table, Donkey & Stick, serving up sandwiches, and Lito’s Empanadas original from Lincoln Park. The cafe turns into a bar in the evenings and you can also peruse their books and record shop. No reservations MONDAY thru FRIDAY 8:00AM–8:00PM $$

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Time Out Market Chicago

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Time Out Market is a curated food hall in the West Loop filled with stands by Chicago's top chefs. There's Bar Goa serving Indian-inspired cuisine, Urbanbelly with "Asian Fusion Fare", and Gutenberg for German-inspired burgers. They are serving up drinks in both the main bar and rooftop bar. Whatever you're craving, you can find it here! No reservations Mon–Fri: 8am–10pm (bakery opens at 8am; all other kitchens open at 11am) Sat: 9am–10pm (bakery opens at 9am; all other kitchens open at 11am) Sun: 9am–9pm (bakery opens at 9am; all other kitchens open at 11am) $$

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Tour Recommendation

If you want to try all of the iconic Chicago food in one go, check out this tour to guide you through the eats. You'll start at Lou Malnati's Pizzeria for that classic Chicago pie then move up Magnificent Mile for the Chicago hot dog. The tour ends at Millennium Park where you can get 2 free hours of bike or kayak rental included as part of the tour ticket.

Chicago Favorites Ultimate Food and Walking Tour

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Bars

Food and drinks go hand in hand, and Chicago's nightlife keeps up with the standards set by their food scene. You'll find many rooftop bars to enjoy the Chicago skyline, speakeasies to step into another world, and cocktail bars to explore your senses. For a more casual drink, Chicago neighborhoods still have their favorite dive bar. 

Cindy's Rooftop

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Cindy's Rooftop is a great place to grab and drink and enjoy a view of Millennium Park. They are located on the roof of the Chicago Athletic Association providing a view from the park all the way out to Lake Michigan. You can enjoy cocktails, beer, and wine on the terrace or sit down in the main dining room for a meal. Reservations for dining only; walk-in standing room on the terrace for cocktails. Monday - Thursday 11am - 11pm Friday 11am - 12am Saturday 10am - 12am Sunday 10am - 11pm $$

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Three Dots and a Dash

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Three Dots and a Dash is a speakeasy tiki bar located in the River North neighborhood. You enter through the back alleyway and are then transported to a tropical paradise. They have your classic tiki drinks as well as some seasonal offerings, all served in fun decorative vessels. Reservations recommended for a table; walk-ins welcome for bar seating Sunday - Wednesday: 4pm - 12am Thursday - Friday: 4pm - 1am Saturday: 2pm - 1am $$

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Kumiko

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Owned by award-winning mixologist Julia Momosé, Kumiko is a Japanese-inspired dining bar that treats both food and drink with equal reverence. They pride themselves in the art of cocktails, using ingredients like rice vodka, sake, and yuzu alongside house-made infusions to create unique flavor combinations. You can order small plates like wagyu katsu sandos or crispy karaage to pair with your cocktail or opt for the seasonal tasting menu. Asian-owned; reservations highly recommended, walk-ins for one or two people at the bar Wednesday - Sunday, 6:00 pm - midnight $$$

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The Aviary

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Conceptualized by Michelin-starred Chef Grant Achatz, The Aviary is an innovative cocktail bar that pushes the boundaries of mixology. Their bartenders craft their cocktails with a focus on theatrical presentations and unexpected flavor combinations. Taking a "fine-dining" approach to cocktails, they offer a multi-course cocktail journey with or without accompanying food pairings. Reservations recommended Su-Th: 5pm - 12am F: 5pm - 1am Sa: 4:30pm - 1am $$$

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Green Mill Cocktail Lounge

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The Green Mill is famous for being Al Capone’s Prohibition-era hangout. Today, they are one of the city's best jazz clubs hosting live music everyday. Come in for a drink, jazz bands, and a piece of history. No reservations, walk in only, cash only Sunday - Thursday, 4pm to 1:11am Friday, 4pm to 2am Saturday, 1pm to 2am $$

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Tour Recommendation

If you're more into beer than cocktails, consider taking this guided brewery tour. You'll learn about Chicago’s brewpub scene and taste different types of craft beer while riding this Prohibition-era-styled barrel bus!

Chicago Craft Brewery Barrel Bus Tour

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Happy Travels

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