Chicago River Cruises, Outdoor, & Water Activities for Your Trip

By Katie Sagal

While you certainly won’t be out on the water year round in Chicago, late spring to early fall are wonderful times to be enjoying the many outdoor water activities available to visitors. You’ll get to see more of the city, and learn about the crucial waterways that have meant so much to the history and development of Chicago River to Lake Michigan. Options include everything from themed cruises (architecture-related, of course!), to scenic lake tours and beyond. Some of the outdoor and water activities you can enjoy in Chicago include:

  • Chicago Architecture River Cruise
  • Classic Lake Tour
  • Tall Ship WINDY
  • Big Bus Chicago Sightseeing Tour
  • Navy Pier

Save on Chicago Cruises & Other Outdoor Activities

Regular admission to a number of these cruises and other outdoor activities are available on the Go Chicago Card. Choose as you go from popular attractions and save up to 55% on combined admission vs paying at the gate. Check out all Chicago sightseeing passes, attractions and prices.

Chicago Architecture River Cruise

Image of City, Metropolis, Urban, Cityscape, Water, Waterfront, Boat, Vehicle, Condo, Housing, High Rise, Ferry, Office Building, Person, If you’re looking to learn more about the distinctive history of Chicago, then this cruise is the one for you. A leisurely, 75-minute-long cruise that floats along the Chicago River, this excursion is an ideal way to see the city from a unique perspective while getting those great Instagram shots. Along the way, you’ll have all the major highlights pointed out and explained, including structures by Mies van der Rohe, Skidmore Owings & Merrill, Helmut Jahn, and more. (And if you don’t know who those architects/firms are, this tour will be even more enlightening!) With more than 40 Chicago landmarks highlighted – from the Tribune Tower to Marina City – you’ll be endlessly fascinated by everything you sail by. Getting In: Chicago Architecture River Cruise admission is included with the Go Chicago Card.

Classic Lake Tour

Image of Boat, Ferry, Vehicle, Person, Yacht, Sailing along Chicago’s impressive skyline on Lake Michigan is a great compliment to the aerial views you’ll get from places like 360 CHICAGO (which we’re sure is part of your itinerary already). This 40-minute cruise features all the historical and cultural attractions along the lakefront, from Navy Pier to Museum Campus. Especially during the steamy Chicago summers, an hour or so spent out on the lake is a great way to cool off – and learn something new! Your professional tour guides will regale you with all-important info, and keep it entertaining. Getting In: Classic Lake Tour admission is included with the Go Chicago Card.

Tall Ship WINDY

Image of Boat, Sailboat, Vehicle, Yacht, Flag, Go on an adventure you’ll never forget aboard the famed Class-A Tall Ship, “WINDY.” This 150-foot-tall schooner is Chicago’s official tall ship, and is a delight to ride for sailing enthusiasts of all ages. Depart from Navy Pier (where you’ll find plenty of other attractions, too – as you’ll find out below), and set out onto the open waters of the expansive Lake Michigan. Sit back, relax, and enjoy the views. Or, if you’re feeling so inspired, help out the crew with a little help around the ship (like assisting in hoisting the sails, for example). You can actually choose from a few different themed sails, too, so customize your trip to suit your interests. Pick from the Skyline Sail with Tales of Real Pirates or the Lakeside Architecture Sail. Getting In: Tall Ship WINDY admission is included with the Go Chicago Card.

Navy Pier

Image of City, Urban, Person, Amusement Park, Ferris Wheel, Fun, Cityscape, Take the whole family to Navy Pier for an afternoon of wonder and delight. Here is where many of your cruises depart from, and also where you can find bike rentals, museums, and of course, the amusement park rides we all love so much. Ascend to the top of the Navy Pier Centennial Wheel to see the Lake in all her glory – especially cool during the evenings when the skyline is illuminated and the sunset is coloring the lake something fierce. Another fun stop is the Chicago Children’s Museum (admission also included with our pass), which is perfect for little ones looking to learn and play. Or, for everyone, the Chicago Shakespeare Theater offers diverse entertainment all year round. Getting In: Navy Pier ride admission is included with the Go Chicago Card.

Hop-on Hop-off Tour by Big Bus Chicago

Image of Bus, Vehicle, Tour Bus, Person, Double Decker Bus, While this bus is unfortunately not able to travel underwater like it’s on some kind of Ms. Frizzle adventure, you’ll still enjoy being out of doors during the warmer months in Chicago. Choose this bus tour for the entertaining and informative narration about the major landmarks and neighborhoods of Chicago – and its got some pretty impressive range, too, so you won’t just be confined to downtown. A hop-on hop-off option is particularly smart because it allows you to personalize your trip – disembark when you see something that interests you (perhaps at the Museum Campus?), and then get back on when you’re ready to explore further. Getting In: Big Bus Chicago admission is included with the Go Chicago Card.

Chicago Water Taxi

Plain old cabs? Forget about them! Get around Chicago on their water taxi system, which can drop you off at any of seven different dock locations along the Chicago River. Even if you don’t need to use it for transit purposes, it’s a fun thing to say you’ve done and a great way to see the city from the perspective of the locals. Most trips are brief (only about 15-30 minutes long), but can take you all along the waterfront from Union Station to LaSalle/Clark and beyond. Check out their map in advance for information on how to get where you want to go! Getting In: Chicago Water Taxi is separately ticketed and is not included with the Go Chicago Card.

Remember to Save on Admission

This spring and summer, when you’re looking for some Chicago cruises and other outdoor fun in the Windy City, keep a few of these top attraction options in mind. They’ll showcase the best of the city, and provide a ton of fun while doing so. Happy travels!

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Best Nightlife in Chicago

With new bars popping up seemingly each week and last call at 4 am for late-night spots, Chicago is a city just made for partying. Whether you want to drop a cool few hundred on bottles of champagne or enjoy dollar beers at a small dive bar, there’s a range of options for all tastes. Of course, everyone has a different style when it comes where they like to eat, drink, and dance. That’s why we’ve put together a guide to the best nightlife in Chicago based on what kind of vibe you’re looking for. Best Tiki Bar: Three Dots and a Dash This may seem oddly specific, but trust me—it’s worth checking out Chicago’s best tiki bar for the experience. Three Dots and a Dash offers a wide range of cocktails served in traditional tiki glassware, complete with the requisite flower and fruit garnishes. Because the venue is actually below street level, the lighting here is a bit dim any time of day, so it’s easy to lose track of time here! Choose from more than 200 different rums to customize your drinks. View this post on Instagram A post shared by Three Dots and a Dash (@threedotsandadash) on Jun 2, 2019 at 12:11pm PDT Best Margaritas: Mercadito Hands-down favorite for best margaritas in a city just bursting with Mexican fare is Mercadito. They offer a variety of different distinctive cocktails alongside the margaritas, including an entire range of mezcal drinks. The décor is also particularly lush and evocative, making this another popular date night spot. Bonus: they’re also among the best for Mexican fare, including high-end craft tacos. Best Date-Night Spot: Arbella If you’ve got a bit of a healthy budget and are looking for that perfect special occasion destination, then look no further than Arbella. This gorgeously-appointed lounge serves up globally inspired cocktails alongside tasty small plates and a full food menu. They have a good happy hour from 5-7 during the week if you need to save some cash. Plus, Arbella also features innovative DJs on the weekend nights, making this a great party place, too. View this post on Instagram A post shared by Arbella Chicago (@arbellachicago) on May 25, 2019 at 7:00pm PDT Best Happy Hour: Franklin Room If you love inexpensive wine, cheap beer, and $1.50 oysters, Franklin Room’s happy hour should be on your list. The specials vary daily, but they always have dollar beer & wine plus $3 martinis at lunch time as well as oyster specials from 5-6:30 every day. Other specials include half-priced bottles of wine on Mondays and half-priced glasses of sparkling wine from Tuesday through Saturday. View this post on Instagram A post shared by Sharzad Kiadeh (@sharzadkiadeh) on Aug 4, 2015 at 7:25pm PDT Best Irish Pub: Lady Gregory’s This is a pretty tricky category to figure out in a city like Chicago where Irish heritage is strong, but Lady Gregory’s is unique enough to standout from the crowd. They feature Irish drafts plus an expansive whiskey menu (one of the best in the city), and offers cozy digs to hang out in. If you’re looking for food, Lady Gregory’s is an upscale option with farm-to-table Irish fare plus some unexpected extras. Best Spot for Bubbles: Pops for Champagne Enjoy cocktails and a frankly almost-intimidating champagne list at this upscale venue. They also have carefully-curated small bites plus frequent live jazz, making this another excellent option for a date night or special occasion, too. It’s also one of the city’s top night clubs, with its late-night music and even better late-night drinks. View this post on Instagram A post shared by Cara Alwill Leyba (@thechampagnediet) on Apr 23, 2015 at 4:00pm PDT Best Beer Bar: Bangers & Lace It’s hard to sum up what makes this Wicker Park legend practically perfect, but it comes down to some combination of their frequently-rotating draft beer list of more than 30 options and the curated vinyl sets the bartenders play. With funky décor and low-lighting, it’s a perfect place to spend a cold winter night, especially when you opt for that rare barrel-aged stout. Best Sports Bar: Hopsmith Tavern This is another tricky one, but I’m going to go with a personal favorite here. Hopsmith Tavern boasts dozens of draft beers that change regularly, plus cocktails and great happy hour deals. With televisions scattered all throughout this historic venue, you’ll enjoy the comfortable mix of the best of modern sports TV alongside River North charm. They also have a rewards program as part of Big Onion Tavern Group that’s worth signing up for if you live in the area and plan to hit up Hopsmith often. View this post on Instagram A post shared by Hopsmith Chicago (@hopsmithchicago) on Jun 8, 2019 at 9:50am PDT Best Dive Bar: Delilah’s The punk-rock aesthetic of this grungy dive bar makes it the perfect setting for guzzling down their dollar beers. On the other hand, they also offer rare craft beers and whiskeys, so even your choosier friends can enjoy an evening here. There are frequent themed music nights, too, with everything from metal to country. Check out their periodic special events, like rare beer tasting festivals that bring out their special reserves for all to try. Best Tap Room: Half Acre (Balmoral) There are more tap rooms in Chicago than you can shake a stick at, but Half Acre’s new Balmoral location is by all reports (and my own experience) one of the best. It’s a bigger space than their original Lincoln Square location, and offers more diverse and rare beer. You can get bottles and drafts of only Half Acre beer, including brand new stuff they’re just trying out. They also have some tasty food to satiate your beer-induced cravings. View this post on Instagram A post shared by Maine Beer Company (@mainebeerco) on Aug 23, 2015 at 5:38pm PDT Best Gastropub: Forbidden Root A venue that also brews their own botanical beer, Forbidden Root in Ukrainian Village is something of a hidden gem. It’s off the beaten path for tourists but is well worth the bus ride to enjoy their wide-ranging explorations in the beer world. Try their strawberry basil hefeweizen, the boozy sparkling rosé ale, or any of their New England IPA series. It’s all brewed with extra botanical ingredients like herbs and fruits, making for a distinctive take on many popular beer varieties. Oh, and they have a delicious full menu—especially brunch. There are obviously hundreds more bars in Chicago to choose from, but it would be futile to attempt a comprehensive list of all the best bars. These listed here are some of my personal favorites, and bars that I would recommend to friends. I hope you enjoy checking out these top spots for the best nightlife in Chicago. And remember, always take public transit, a taxi, or a rideshare home after you’ve been out partying. It’s incredibly easy to find a taxi or Lyft/Uber in Chicago if you’re out after the CTA stops running. You can also download apps like Curb to request a taxi just like you would with Lyft. Have fun! Enjoyed reading this? Find out all about Chicago's party of the year, St Patrick's Day, and start planning your trip for next year. Or, plan your entire city vacation with our handy guide to Chicago.
Katie Sagal
St Patrick's Day Chicago
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How to Celebrate St. Patrick’s Day in Chicago

St. Patrick’s Day is a holiday beloved by many, but it’s particularly special to Chicagoans. As a city with a vibrant Irish heritage—and an even more enthusiastic Irish-American population—Chicago is the perfect place to celebrate St. Paddy’s. From dyeing its iconic river a vivid green to holding one of the best St. Paddy’s parades in the US, Chicago goes all out for this holiday. Here’s a guide to what to do, where to go, and how to enjoy St. Patrick’s Day in Chicago. So put on your best, brightest green outfit and get ready to celebrate.  Dyeing of the Chicago River Each year on the Saturday before St. Patrick’s Day, the city of Chicago dyes its famous river a lush bright green. This is a cherished tradition dating back over 50 years and is one of the highlights of any celebration. Every year spectators from across the city and around the country line the bridges and riverwalk to watch the barges release the dye into the water and see the river slowly turn emerald green. They use organic dyes that are safe for the environment; as a result, the color only lasts for about five hours. The dyeing begins at 9 am, so get to the river early in the day if you want to see the color in its full glory. St. Patrick’s Day Parade One of the largest St. Paddy’s Day parades in the country, Chicago’s vibrant version of an Irish-American classic, is legendary. This downtown celebration traverses Columbus Drive, heading north from Balbo to Monroe. Columbus Drive divides Millennium Park and Grant Park in half, so the parade route is a scenic one. The parade usually begins at noon, so arrive early to grab a good spot. You’ll enjoy plenty of green, white, and orange outfits, Irish step dancers, marching bands, elaborately decorated floats, and even bagpipers (of course!) Other St Patrick's Day events in Chicago There are plenty of things to do across Chicago to celebrate your favorite Irish holiday. Check out a few of these local events & activities to make the most of your time in the Windy City. St. Patrick’s Festival at the Irish-American Heritage Center: Held after the parade, this family-friendly event offers traditional and contemporary dance performances alongside tasty food and drink. A good option for those traveling with kids.   South Side Irish Parade: Another great family-centric event, this smaller but no less enthusiastic parade begins at noon on the Sunday nearest St. Paddy’s Day, setting off from 103rd Street & Western Avenue.   Shoreline Cruises Architecture River Cruise: While this architecture cruise also runs regularly on days the river isn’t green, the cruises today are especially popular. Get up close to the emerald waters and snap those perfect Instagram shots while learning all about the city’s built environment.   Leprechaun Leap: This popular race offers 5k or 8k courses along the gorgeous Lake Michigan waterfront. It’s been a beloved tradition among runners for nearly 20 years now, and attracts participants from all over. Dress in costume for the most fun!   Hop-on Hop-off Chicago City Tour: See more of the city with a hop-on hop-off tour from Big Bus. Take advantage of their local expertise to get some advice on what else to do to celebrate, and get around the city easily. Places to eat & drink on St. Paddy’s Day in Chicago One of most people’s favorite things about St. Patrick’s Day is the opportunity to enjoy delicious Irish food and a pint or two of plain (aka Guinness). Scope out these bars and restaurants while you’re in town for the holiday. Many places will have special events on, some requiring advance tickets, so these aren’t your only options by any means. If you’re traveling with an adults-only group, you may also want to consider a pub crawl through River North (Division Street is always popular). Remember, bars in Chicago stay open very late if you need an excuse to keep the festivities going. Kerryman Irish Bar & Restaurant: This River North mainstay is perfect for those looking to enjoy traditional Irish fare with a bit of a modern update.   D4 Irish Pub & Café: Think Irish food with some modern American flair thrown in: fish and chips or corned beef and hash, plus avocado toast and lobster mac n’ cheese.   Lady Gregory’s: An Andersonville legend, Lady Gregory’s is a must-visit destination for whiskey connoisseurs. With more than 300 options to choose from, make sure you take advantage of their full dining menu to balance it all out.   The Galway Arms: Found just west of Lincoln Park (right near the zoo), the Galway Arms has been voted Best Irish Pub for four years running. Enjoy its cozy historical vibe and scrumptious authentic cuisine.   The Grafton Pub & Grill: Located in Lincoln Square, this traditional Irish pub features tasty burgers with an extensive whiskey menu. They’re always good for some Irish-American music, too. Tips for Booking St. Patrick’s Day Hotels If you do intend to make St. Paddy’s in Chicago a part of your next getaway, be sure to plan in advance. Hotels book up fast, and crowds are thick around the riverfront and parade route. Check out our logistical tips for a smoother vacation. Because St. Patrick’s Day is such a big holiday for the city of Chicago, many hotels will run special deals or discounted rates around this time of year.    If you are a member of a hotel’s reward program, it might be a good idea to cash in some points now. You can reserve in advance and pay less than you would otherwise.   Even if you aren’t sure of your plans, book your hotel room at a refundable rate that you can alter later if necessary.   Aggregate sites like Trivago, Hotels.com, and Expedia can be good resources for finding affordable hotels. Keep in mind that some sites may require that you pay for the full price of the hotel upfront.   Look for hotels outside the immediate downtown area. While you probably want to stay in the Loop to be near the parade and other Chicago attractions, you don’t need to stay right off Millennium Park to be close. River North or Lincoln Park are great neighborhoods to find hotels that won’t be as full. Some useful Chicago resources to help you plan your trip Check out the top things to do in Chicago, things to do when it rains in Chicago, and museums you must visit on your trip to the Windy City. Share your adventure with us Remember to tag @GoCity in your holiday snaps and we might just feature you on our socials. Follow the Go City Instagram and Facebook pages for competitions, special offers, and inspiration for your chosen destination. Want to save money on those bucket-list attractions? Check out passes from Go City and you could save yourself up to 50% on your must-sees – perfect! ☀️Compare Chicago passes☀️ – 🌏 Explore other destinations 🌏 – ✈️ Buy a pass ✈️
Andrew Martineau
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Best Time to Visit Chicago

Chicago is one of America’s premier tourist destinations. With world-class museums, globally influenced dining, and luxury shops galore, Chicago attracts millions of travelers each year. While most folks visit in the summer due to a combination of school vacation and the ability to take time off work, the best time to visit Chicago is actually not the middle of the summer. For most people, Chicago weather can be a real determining factor in when to visit this stellar city. It’s chilly – often bitterly cold – during the period between November and March, so most people avoid trips to Chicago in winter. On the contrary, the best times to visit Chicago are late spring/early summer, and early fall. Because travel plans can vary, however, and you may not be able to target that ideal weather in Chicago, we’ve put together a run-down of the best things to do in Chicago year ‘round, along with highlights of the best times to visit. April – May (Best Time to Visit) Chicago is warming up from a long, cold winter, and the weather is reliably between the high 50s and low 70s (mid-teens to low 20s Celsius). This is also a time of year when the flowers are blooming, the parks look their finest, and everyone in the city is relieved to have survived another winter. Some top things to do during this time of year include: Macy’s Flower Show (ends mid-April) – held in their iconic State Street location (formerly Marshall Fields), this lush display of locally grown flowers brightens up the store. Get some souvenirs here, or just indulge in some retail therapy. Chicago Cubs & Chicago White Sox Games – Celebrate your love of baseball by visiting either of the city’s ballparks for their opening day games, usually in early April. Chicago Science Fest (mid-May) – with dozens of events, workshops, and speakers, this science-themed event is great for adults and kids. Events are held at top venues throughout the city, including Adler Planetarium. Maifest Chicago (late May – early June) – a free, German-inspired cultural festival with food, music, and dancing. It’s a family-friendly event held each year in the up-and-coming Lincoln Square neighborhood. Navy Pier Summer Fireworks (Memorial Day – Labor Day) – this event will recur periodically throughout the entire summer, but this perennially popular fireworks show is a major part of Navy Pier this time of year. View this post on Instagram A post shared by GoCity® (@gocity) on May 15, 2019 at 6:27am PDT June - August The heart of summer is the most popular time to visit Chicago, but that also means that hotel prices will be the highest and lines will be the longest. Plan to book ahead as much as possible, too, as many things will sell out quickly. The weather is will likely range between the high 50s and low 80s (mid to high 20s Celsius), but could also have tremendous variation. Here’s a selection of some of the most popular things to do in Chicago in the summer: Lake Cruises (June – August) – take a leisurely sightseeing cruise on Lake Michigan to enjoy the beautiful weather and play the tourist without much effort. Grant Park Music Festival (June) – this free event offers some of the best classical music performances in the city in one of our most beloved parks. Spend a day at the Art Institute, and then enjoy a performance with a picnic dinner in the evening. Hyde Park Brew Fest (early June) – an adult-friendly event, this beer-sampling weekend is a good way to relax after a day spent with the kids at the nearby Museum of Science and Industry. Taste of Chicago (July) – come sample the city’s tastiest cuisine alongside foodie locals at this gorgeous lakefront location in Grant Park. Enjoy dance and music performances as you munch. Lollapalooza (August) – a pricey event to be sure, but it’s one of the country’s most popular music festivals and is worth the price of admission to see your favorite act in this legendary setting. September – October (Best Time to Visit) The summer crowds have mostly died down, and the temperatures will mellow out without getting too frigid just yet. You can expect the day to be somewhere around the high 60s to high 70s (low 20s Celsius), but at night it can get pretty chilly so definitely wear or pack layers. You should also keep in mind that some tours may switch to winter hours (or stop operation altogether). If you’re in town in early fall and looking for things to do, check out our top picks: Chicago Architecture Biennial (begins in September) – this event only pops up every two years, but it’s worth the opportunity to explore the fantastic architecture of Chicago. Visit the Chicago Architecture Center or take an architecture cruise to complete the experience. Donut Fest at the Zoo (early September) – Lincoln Park Zoo hosts this family-friendly event, offering behind-the-scenes animal access alongside drinks for the adults and donuts for all. Chicago International Film Festival (mid October) – held at various locations throughout the city, this highly regarded indie film fest showcases the best in the media and is a must-do for film buffs. Chicago Marathon (mid October) – while you may not be running this iconic race, it’s worth a few moments of your time to cheer on these amazing athletes and their quest for glory. Sightsee up High – one of our favorite things to do in the fall is to see the city from above. Check out 360 CHICAGO, for one, to see the fall foliage and the changing lakefront neighborhood. View this post on Instagram A post shared by GoCity® (@gocity) on May 13, 2019 at 7:08am PDT November – March The coldest time of the year in Chicago and the least popular time for tourists to visit, the winter can be a real doozy. Temperatures can vary significantly, with everything from periodic days in the 40s to sub-zero temps (single to negative digits Celcius and Farenheit). Dress warmly, but hide inside at museums and other attractions where you can. There are still plenty of great winter events in Chicago, including some of my personal favorites: Meet the Animals – Among the best places to stay away from the chill while also taking advantage of the thinner crowds is the Shedd Aquarium. It’s difficult to get in without long lines in the summer, so a wintertime visit is perfect. Magnificent Mile Lights Festival (late November) – a prelude to the holiday season, this exciting festival illuminates the city’s most popular shopping district. Grab some hot cocoa before you watch the parade, though. McDonald’s Thanksgiving Day Parade (Thanksgiving Day) – with a bevy of themed balloons and floats, this parade is beloved among children and families. Plan ahead if you want to find a space along the parade route. Christkindlmarket (mid November – end of December) – visit one of the most popular indie holiday shopping destinations in the city in search of some unique crafted object. Don’t miss out on the souvenir cider mug, either. ZooLights (end of November – early January) – a long-standing tradition in Chicago, the Lincoln Park Zoo lights up the night with its animal-themed illuminations. If you’re looking for more things to do in the park during the day, then you could also consider the Chicago History Museum. St. Patrick’s Day Parade & Festivities (St. Patrick’s Day) – One of Chicago’s favorite holidays is St. Paddy’s Day, a time when everyone comes together to celebrate their Irish heritage, real or imagined. They also famously dye the Chicago River green, so come for the pictures if nothing else! Save on Admission to Chicago Activities & Attractions Plan your trip during the best time to visit Chicago, or brave the weather and forge ahead with a winter trip or summertime sojourn. Regardless of when you visit the Windy City, you’ll want to be smart about your budget. Pick up a Go Chicago pass to save on admission to many of the city’s top attractions so you’ve got more money in your pocket for popular festivals and events. This all-digital, smartphone-friendly pass is the easiest way to see Chicago and save. Share your adventures with us Remember to tag @GoCity or use the hashtag #GoCityPass in your holiday snaps 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!
Andrew Martineau

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