Ultimate Chicago Bucket List

By Katie Sagal

With such a diversity of cultures, attractions, cuisines, and neighborhoods, Chicago is just bursting with exciting things to do for locals and visitors. Whether you’re a long-time Chicagoan or a newbie trying out the ropes, we’ve pulled together our favorite things to do in this marvelous city. This ultimate Chicago bucket list isn’t completely exhaustive but it’s a good start for those who hope to enjoy the best and most unique things that the Windy City has to offer. In no particular order, please consider:

Chicago Bucket List 1-10

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  1. Visit the Lions at the Art Institute. One of the best art museums in the world, Michigan Ave. entrance to the Art Institute of Chicago is also guarded by some of the most famous lions.
  2. Go ice-skating at Maggie Daley Park. With their own modest ice-skating ribbon, Maggie Daley Park is a great winter destination for families.
  3. Ride the Centennial Wheel. This Navy Pier icon is perfect for dates or entertaining the kids. Check out the new rooftop bar while you’re at it.
  4. See the summer fireworks at Navy Pier. You can take a cruise to see them closer, but the views from the Pier itself are pretty good, too.
  5. Compare the views. Chicago boasts two main observation decks—SkyDeck Chicago and 360 CHICAGO. Try them both to see which you like best.
  6. Savor deep-dish pizza. One of Chicago’s most famous culinary exports, deep-dish pizza is a must. Try Gino’s East (just off Michigan Ave.) for some authentic options.
  7. Snap your photo with the world’s most famous dinosaur. SUE the T. Rex, at the Field Museum, is the largest and most complete T. Rex skeleton in the world. Get a selfie with it to soak up the celebrity vibes.
  8. Tour Wrigley Field. Or cheer on the Cubs. Either way, the world-famous Wrigley Field is a must-see for all Chicago visitors.
  9. Go shopping. Chicago is a shopping capital of the country, with options ranging from luxe Oak Street to eclectic Wicker Park.
  10. Take a cruise on Lake Michigan. If you’ve never enjoyed an excursion out on a lake so big that it has tides, this Lake Michigan cruise is perfect.

Chicago Bucket List 11-20

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  1. Sample craft brews. Chicagoland has more breweries than any other metro area in the country, and many of them don’t export. Snag that rare Forbidden Root IPA while you can.
  2. See some Frank Lloyd Wright architecture. This iconic American architect called Chicago home for many years, with great examples of his Prairie Style architecture like the Robie House still around to explore.
  3. Enjoy the nightlife. With bars that close at 4 AM and a selection of venues offering everything from expensive champagne to dollar beers, the Chicago nightlife scene is unbeatable.
  4. Put the kids on a historic carousel. The Lincoln Park Zoo boasts an endangered species carousel comprised of 48 artisan-made wooden animals—an artistic marvel in the age of all things plastic.
  5. Take an architecture tour. Even locals love the chance to explore the city’s multi-faceted architectural history. Options include architecture cruises, bus tours, walking tours, or even Segway tours.
  6. Dine at the Walnut Room. Located in Macy’s on State Street, this iconic restaurant is most popular at Christmastime when you can see their annual tree.
  7. Roam Millennium Park. This massive urban park includes landmarks like the Pritzker Pavilion (home to free concerts in the summer) and public art like “Cloud Gate” (also known as The Bean) and the official Chicago Christmas Tree in the winter.
  8. Tour the historic Chicago Theatre. Boasting one of the most iconic marquee signs in the city, the Chicago Theatre also has a lot to offer inside. Take a tour to see it all.
  9. Explore the Chicago Riverwalk. This revitalized area is a hip place to dine, sip cool drinks, or go on a river cruise.
  10. Bike, walk or run along the lakefront trail. It’s one of the nation’s most beautiful and longest waterfront trails. Rent a bike if you weren’t able to bring your own.

Chicago Bucket List 21-25

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  1. Go on a date at a planetarium. The Adler Planetarium offers monthly Adler After Dark events with music, entertainment, and, of course, star-gazing.
  2. Take in a show. Chicago’s theatre scene easily rivals that of New York City, with more theatres, more shows, and more indie productions than Broadway.
  3. Soak up artistic inspiration. The Museum of Contemporary Art offers an eclectic mix of the most innovative and provocative art being produced around the world. They also have a restaurant, Marisol, which is helmed by one of the city’s top chefs.
  4. Party at a music festival. Lollapalooza is one of the biggest and most diverse music festivals in the United States, as well as one of the most long-running.
  5. Commune with nature. The Garfield Park Observatory is an oasis in the middle of the city, bursting with greenery and lush indoor gardens that visitors can enjoy for free year-round.
Save on Chicago Bucket List Ideas Many of these ultimate Chicago bucket list ideas are included on the Go Chicago pass. This convenient digital pass provides up to 55% on combined admission prices to the city’s best attractions and activities. Share Your Adventure with Us Tag @GoCity or use the hashtag #GoCityPass in your vacation photos and we'll feature you on our page. Follow the Go City Instagram and Facebook pages for competitions, special offers, and events and inspiration for your chosen destination, too!

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A visitor viewing the art museums of Chicago
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Best art galleries in Chicago

A haven for art lovers, Chicago had more galleries than anywhere in the United States bar New York. Its artistic heritage goes right back to the early days of the city, and has escaped its gallery walls to spread across its streets. Chase Tower Plaza provides a home for Marc Chagall’s Four Seasons mural, Daley Plaza a 50 foot sculpture by Picasso, Brunswick Plaza Miro’s Chicago and Millennium Park Anish Kapoor’s Cloud Gate – otherwise known as ‘the bean’. What’s particularly wonderful about the best art galleries in Chicago is that they encompass all artistic styles and ages – from contemporary photography to outsider art. Nor is it limited to the second city’s grand institutions. Chicago’s smaller independently run art galleries have equally captivating collections. Where should you spend your time as an art lover in Chicago? The answer lies within the next 800 words. Art Institute of Chicago Founded in 1866, the Art Institute of Chicago is the gallery from which much of the city’s pleasure in artistic pursuits has developed. Its collection is both expansive and world class, totaling some 300,000 individual objects from ancient Middle Eastern artefacts to modern textiles. Some of its most famous residents include Hopper’s Nighthawks and Seurat’s A Sunday on La Grande Jatte, alongside Grant Wood’s American Gothic. Museum of Contemporary Art Whilst it cannot compete with the 5000 years of human endeavor covered by the Art Institute, the Museum of Contemporary Art more than holds its own with its rotating series of exhibitions focused on the art of the latter twentieth century to the present day. Its box-like gallery space provides a home for works including Andy Warhol’s Vote McGovern – a ghoulish image of President Richard Nixon. Borrowing much of the art that hangs on its walls both nationally and internationally, a visit is never the same twice. Zolla/Lieberman Gallery It’s only because of Zolla/Lieberman Gallery that the River North Art District exists. When it arrived in 1976, the area was a down-on-its-luck industrial district whose industry had long gone, leaving ‘Smokey Hollow’ all but derelict. Since its first show, the gallery has sought a path which isn’t restricted by either genre or the status of its artist. It supports a great deal of new talent as well as those who have already made their name. Each exhibition lasts just a couple of months. Intuit: The Center for Intuitive and Outsider Art It was the early 1990s which witnessed the birth of Intuit, a gallery created to celebrate and promote the work of outsider and folk artists. It means that many of the 1100 pieces in its permanent collection were created by self-taught artists who felt in some way marginalized, providing a fascinating insight into the thoughts of populations often underrepresented within artistic communities. Their artists may not be household names, but that’s not to say you won’t find something thought-provoking or touching should you choose to visit when in Chicago. Rhona Hoffman Gallery The West Town district’s Rhona Hoffman Gallery is one of Chicago’s small art galleries with a big personality. Heavily involved in community events such as EXPO Chicago, its main remit is to bring young and emerging artists to new audiences. Global in scope, it has historically lent towards female artists, with notables it has championed including Cindy Sherman and Barbara Kruger. As a mixed media gallery, expect anything from video installations to sculpture. Stephen Daiter Gallery Another River North pick, Stephen Daiter Gallery dedicates itself to twentieth century photography from America and Europe. From traditional portraits and still lives to experimental styles and photojournalism, it focuses on the very best vintage photography from the Bauhaus school to the homegrown Chicago School of Design. Its contemporary program brings it right up to date. Vertical Gallery One of the newest kids on the block, Vertical Gallery was the dream of Patrick Hull, former Vice President, Marketing & Sales at Birkenstock USA and opened in 2013. Aiming to rival all the east or west coasts can offer when it comes to street art and pop culture, it has become the jumping off point for several artists entering larger galleries in Chicago and beyond. If their work doesn’t bring a wry smile to your face, you’ll be one of very few who leave unimpressed. Chicago Truborn Literally unmissable due to its front facing multi story mural, Chicago Truborn was unveiled in 2011 as a place to see art in an unintimidating environment. A must-visit Chicago gallery for anyone who’s ever considered becoming a collector, Truborn’s art is some of the most affordable in the city, although this shouldn’t suggest its artists are somehow less talented. What’s more, there’s a new exhibition every five weeks to look forward to from the hottest crop of street, urban and graffiti artists. Corbett vs Dempsey The Corbett in question here has taught at the Art Institute of Chicago for more than 40 years, whilst Dempsey has had an illustrious career as the house manager of a Chicago film center. The result is a gallery just as eclectic. The mix of brick, plaster and polished floors shows off the contemporary paintings well, with film and musical works creating a very special ambience. There’s also an art bookshop and record store selling the gallery’s Corbett vs Dempsey label, whose list contains the likes of Sun Ra. Chicago Gamespace Much has been made of the artistic integrity of video games in recent years, and Chicago Gamespace came about as a living museum of the most important arcade games – most of which can be played. As well as a permanent collection of machines from Pac-Man to Mortal Kombat, the walls hang with stills and origin artworks, with prints available from the onsite shop. Roughly a mile west of Chicago History Museum and the animals of Lincoln Park Zoo, the only downside is that Chicago Gamespace is only open on Sunday afternoons. See the best art galleries in Chicago with Go City What unites the best art galleries in Chicago isn’t the size of their permanent collections or the focus of their curatorial teams, but the energy and love they put into sharing their art with the public. Big and small, classic and contemporary, together they form one of the most important cultural gatherings in the entire country. Head to Chicago with Go City and you can bask in reduced admission to many of the windy city’s top attractions, including the Museum of Contemporary Art.
Ian Packham
Chicago
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Chicago itinerary – 3 days in Chicago for first timers

Chicago offers diverse cultural experiences, world-class museums, exciting culinary adventures, and renowned architecture.
Katie Sagal
Chicago
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Romantic Things to Do in Chicago - Valentine's Day & More

Looking to plan a romantic getaway with your sweetheart? There are so many wonderfully romantic things to do in Chicago that it’s hard to choose our favorites. If you’re looking for romantic things to do in Chicago, either for Valentine's Day or for a romantic trip any time of year, check out a few of our top suggestions. The Signature Lounge at Hancock Center Located atop the well-known John Hancock Center you'll find the romantic cocktail bar known as The Signature Lounge. The view from the 96th floor is phenomenal (to say the least), and the food and drink are equally exquisite. This is the perfect spot to wind down after a busy day or get geared up for a romantic evening out. Keep in mind that this venue is in high demand, and will both fill up quickly and come at a high price per drink. (I, for one, tend to limit myself to sipping a single drink slowly to enjoy the view.) If you'd like the take this evening to the next level -- literally -- a visit to 360 CHICAGO (just a bit lower on the tower) is a delightful addition to a romantic drink or two. You'll get to see the city skyline from above, including the shoreline of Lake Michigan and the easily identifiable Navy Pier Centennial wheel. Skydeck Chicago (top of Willis Tower) Looking out from the Skydeck Chicago observation deck at the top of the Willis Tower (formerly Sears Tower) is one of the most romantic things to do in Chicago. You'll enjoy 360-degree views from the second tallest tower in the western hemisphere, taking your love to new heights in a serious way. For the most romantic view, head to the Skydeck at sunset or after dark when the city lights are glowing. Explore the Art Institute of Chicago If you’re a fan of art, then there are few places as romantic, in Chicago, as the #1 rated museum in the country, the Art Institute of Chicago. They’ve got some of the best collections of Impressionist Art, some gorgeous Chagall stained glass windows, plus an impressive array of sculpture, textiles, antiquities and more. Check out their seasonal special exhibits for details on new and exciting things on display right now, or hit up their permanent collections for a few love-themed pieces like their collection of 19th century Valentines and sexy photographs. Centennial Wheel at Navy Pier This 15-story Centennial Wheel is located at one of the most visited attractions in Chicago, at the exciting Navy Pier. Recently redesigned as part of their centennial project, the Centennial Wheel offers beautiful sights at thrilling heights. You can even enjoy free days once per month! From the top of the famous Centennial wheel, you and your partner will escape the crowd for a few minutes for some alone time with the scenic skyline and Lake Michigan views. After you disembark from the Centennial Wheel, Navy Pier is a lakeside wonderland to explore. You'll find romantic restaurants, shops, and other top-class attractions as you stroll along with your loved one. If you plan it right, you can even pick up tickets to a show at the well-regarded Shakespeare Theater, also located on the Pier. Attend a Show Chicago’s theater scene is pretty unbeatable when it comes to variety and quality of performances. From the traditional (like you’d find at the Shakespeare Theater on Navy Pier) to the avant-garde, there’s something for all tastes. Because a theatrical performance is a pretty hot idea for Valentine’s Day, be sure to secure tickets in advance! You may be able to find discounted tickets by signing up for theater-specific mailing lists and websites like Goldstar. Stroll the Beautiful Parks While Millennium Park is often the favorite for cultural activities and current events, Grant Park has just as much in the way of sightseeing and beautiful scenery. Or, check out the Lurie Garden to find the hidden beauty of wintertime plants. Whichever venue you choose, the real treasure is in the journey. If you’re planning a date in the warmer months, be sure to check out Buckingham Fountain, a truly impressive array of water jets set against the impressive Chicago skyline. Of course, if you're visiting during the winter months around Valentine's Day and can't bear the Chicago winter cold, then a visit to the Chicago Botanic Garden is another nice option. Stick with their indoor exhibits to see some lovely tropical plants and flowers. Enjoy a Romantic Meal A romantic dinner is a classic for a reason. It’s hard to go wrong with a well-researched dinner venue this time of year, especially if they’re offering special Valentine’s Day meals or menus. It’s a great break from your own cooking and a good way to pry yourself away from Netflix. Downtown Chicago has tons of great restaurant options, many of which are in easy distance of several other great attractions to help you plan a larger itinerary. Remember to book your table early on a site like OpenTable to avoid last-minute panic! Remember to Save on Attraction Admission So there you have it. Our list of some romantic things to do in Chicago, just in time for Valentine's Day. Remember, some of these great options are included on the All-Inclusive Pass and the Explorer Pass from Go City, where you can save up to 55% on combined admission vs paying at the gate.
Katie Sagal

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