Chicago Labor Day Weekend - 10+ Fun Things to Do in September

By Katie Sagal
Published: July 18, 2024

Labor Day may mark the unofficial end of summer, but it certainly doesn’t mean the end of summer fun! There are still so many great festivals, events, and activities to enjoy that will help you squeeze every last drop of summer out of this last weekend before school starts. If you’re looking for Chicago Labor Day Weekend ideas, check out some of these local activities and fun things do in Chicago in September, including...

  • Architecture River Cruise
  • Architecture Tours
  • SkyDeck Chicago
  • Art Institute of Chicago
  • Navy Pier Centennial Wheel & Rides
  • Brookfield Zoo
  • Bike and Roll Chicago - 4 Hour Bike Rentals
  • Great American Lobster Fest at Navy Pier
  • Chicago Jazz Festival
  • And more!

1. Architecture River Cruise

chicago-river-downtown-skyline-usa

Explore Chicago's unique built environment aboard a Shoreline architecture river cruise. You'll sail down all three branches of the Chicago River and see iconic buildings by Mies van der Rohe, Skidmore Owings Merrill, Bertrand Goldberg and more. The Windy City is well-known for its famous architects and their advancements in the field. There's no better place to take in some of the world's finest buildings and structures!

2. Frank Lloyd Wright Studio & Robie House

If the idea of an architecture cruise was really exciting but didn't seem to go far enough, you'll want to check out some of Chicago's other top architecturally-minded attractions. Head to the Frank Lloyd Wright Studio and Home to tour the living and working spaces of one of the most iconic architects of the last century. You can also scope out one of his famed local projects, the Robie House (on the campus of the University of Chicago, which is a fun area to explore as well). Finally, the Chicago Architecture Center also offers plenty of walking tours, bus tours, Segway tours, and cruises to meet your architectural desires.

3. Art Institute of Chicago

chicago-art-institute-entrance-lion-sculpture

If you're looking to infuse a bit of culture into your Labor Day weekend vacation, then a visit to the world famous Art Institute of Chicago is a smart choice. This award-winning museum is filled with diverse collections of amazing works of art and historical artifacts, from Asian statuary stretching back millennia to modern American and European painting. Some of the summer exhibits they'll have running through Labor Day include the highly-anticipated "Manet and Modern Beauty." See our post on current exhibits at the Art Institute for more information.

4. Brookfield Zoo

zoo-animals-brookfield-zoo

The Brookfield Zoo is the city's largest zoo! The 216-acre park is home to a variety of animals, from Big Cats to the Great Bear Wilderness. See all your favorites, big and small, at exhibits like the Seven Seas or Living Coast.

5. Rent a bike

girl-renting-city-bike-stand-chicago

Of course there’s no place you’d rather be on Labor Day weekend than soaking up the last of the summer sun, so why not spend most of your time outside? There is so much to see and do in the great urban outdoors that is Chicago, so take your pick! Taking a bike for a spin is one of our favorite summer activities. It keeps everyone fit and healthy and is tons of fun to boot. Opt to rent a bike from Navy Pier and pedal along the waterfront and the many miles of lakefront trails in the area. They're immensely popular with cyclists, runners, and strolling families from all across the city, so it's an nice opportunity to see what the locals get up to as well.

6. SkyDeck Chicago

panorama-taken-chicagos-skydeck

Journeying up to the top of the Willis Tower to SkyDeck Chicago and stepping out on The Ledge is a must on any Chicago vacation. This impressive observatory is one of the best in the city. Keep in mind that the Ledge attraction is one for the bravest among you -- you'll step out onto a solid glass floor that looks down onto the city below. At 1,353 ft in the air you'll see the Windy City in its entirety. From Navy Pier to Soldier Field, Chicago will be at your feet. Make sure you bring a camera!

7. Navy Pier

chicago-navy-pier-ferris-wheel-entrance

Navy Pier is the quintessential Chicago attraction. It's a great place to visit no matter the season, but its especially lively throughout the summer. If you're traveling with kids, remember that the Chicago Children's Museum is also located on Navy Pier, making it a nice addition to a day of rides and fun for the kids. For the adult groups, be sure to visit the Offshore Rooftop & Bar, located on the third floor of the Festival Hall. It's a hot new venue for summer drinks and bites that's just opened earlier this year and is a must-visit. Plus, it's the largest rooftop bar in the country, so what's not to love? Check out our guide to Navy Pier for more complete information!

8. The Great American Lobster Fest at Navy Pier

aerial-chicago-skyline-sunrise-view-navy-pier

Now in its 6th year, the Great American Lobster Fest returns to Chicago's iconic Navy Pier. It's an event you won't want to miss. The Great American Lobster Fest is the largest lobster and seafood festival in the Midwest. Head down to Navy Pier this Labor Day Weekend to kickoff the end of summer with top notch lobster and seafood dishes, live performances, family games, arts and crafts and more. General admission is free, although lobster meals and VIP tickets are also available for purchase.

9. Chicago Jazz Festival

jazz-bassist-playingvintage-style-photo

This longtime lakefront music festival is a Chicago legend. It’s also been a Labor Day tradition for nearly 40 years, so it’s an important part of the way the city celebrates this great summer holiday. You’ll enjoy free live music performances that range through all varieties of jazz, from local and even international musicians. A visit to this iconic Chicago event is yet another wonderful thing to do this Labor Day weekend, especially for fans of the arts and culture scene. It's also a great excuse to head over to Millennium Park, home of the famous Cloud Gate Sculpture (otherwise known as The Bean).

10. North Coast Music Festival

The North Coast Music Festival brings together artists from all across the spectrum of EDM music. It's also located on the chic Northerly Island concert site, which is an outdoor venue that's just perfect for end-of-summer fun. The North Coast Music Festival is a separately ticketed event, with options for lawn seating, general admission, and VIP tickets.

Save on Attraction Admission

Regular admission to a number of these Chicago attractions are included on the Go Chicago® pass. Choose as you go from dozens of top attractions and save up to 45% on combined admission vs paying at the gate. See all available passes, attractions & prices – Learn more. We hope you consider visiting some of these attractions to help round out your summer vacation in style.

Share your adventure with us

Remember to tag @GoCity 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!

Katie Sagal
Go City Travel Expert

Continue reading

west loop
Blog

Things to do in West Loop, Chicago

Head to Chicago for your vacation and want to know what's good? Give West Loop a try. There's so much to do and see, you might never leave. Here's our list of the best things to do in West Loop, Chicago. Including: Street Markets Park walks Go bowling Get cultural Try climbing and more! Get Marketeering Let's start this shindig with a smattering of shopping. West Loop has an abundance of markets where you can pick up anything from fresh groceries to hand-crafted jewelry. If you're looking to wheel, deal, and shave a few bucks off your purchases, head over to Randolph Street Market. In the summer months, you'll find over one hundred vendors taking over the Chicago Journeyman Plumbers Union Hall parking lot. Within this bizarre bazaar, you'll discover stalls filled with antiques, old records, hand-crafted wonders, and other assorted knickknacks. Or, if food is your purchase of choice, give Chicago's French Market a go. You'll find myriad stalls with fresh produce from all corners of the world, and a host of pop-up restaurants and bakeries selling delicious bites. Rolling down the lanes Do you like balls? Do you hate pins? If you answered yes to both of these questions, this next entry will be for you. Punch Bowl Social has taken over West Loop. Their demands? Maximum fun. Their plan? 30,000ft of retro arcade, karaoke, fine dining, and more bowling lanes than you could shake a used pair of shoes at. Grab a drink, collect some fellows, and go throw some bowling balls down some bowling lanes to drop some bowling pins. It doesn't get much simpler than that. Then, when you're all bowled out, check all the other entertainment on offer, or grab some classic diner food from the on-site restaurant. Yee-haw. It's bowling time, or something. Park Life If the weather is good and you're so inclined, head to a park for a jolly good time! Thankfully, West Loop has some great green spaces, so if you're visiting Chicago, get that green in you. Perhaps its better-known park is Union Park, where the annual Pitchfork Music Festival brings farmers from all across America to get angry at things. Not really, it's a music festival, and a good one at that. However, if you don't make it in July, there's still loads to do. Pools to jump in, courts to play in, and that sweet grass to relax on. Or, if you want to entertain the little ones, stop by Mary Bartelme Park. It has an amazing children's playground with unique and exciting play equipment you won't find anywhere else. It's also good for dogs, if your little one walks on four legs. The Climb Picture the scene. You're a secret agent, climbing up a rocky cliff face. You receive a call on your sweet futuristic sunglasses. It's your secret spy agency, and they have a job for you. You choose to accept it, and throw the glasses off towards the camera as they self-destruct. Yeah! So if the climbing part of that interests you - and nothing else - head on over to Brooklyn Boulders. There, you'll find lots of surfaces to climb, which is what you want. If you're a seasoned pro, feel free to hit the walls and do some sweet flips, or whatever climbers do. If you're new to the climbing game, never fear. They have expert trainers on hand to teach you the tricks of the trade. And who knows, maybe they're secret agents too. Hiding in plain sight, at Brooklyn Boulders. Would you like to play a game? If you go to sleep listening to the distinctive cling of pinball tables and assorted beeps and boops of old arcade machines, you might like this next place. Take a running jump into Emporium Arcade Bar and fall into a world of old-school arcade action. With a slew of pinball-flicking, foosball-spinning, puck-slapping, and pool-shooting fun, it's a lovely place full of joy and smiles. If you have friends, bring them with you, and pump the fun up to stratospheric levels. After you've spent all your money on machines, take out a loan and go enjoy a refreshing cocktail or IPA at the bar. You will love it. Won't you? Yes. Culture! If all of that wasn't fun enough for you, how about a little learning and culture to take that fun factor to the next level? At the National Hellenic Museum in West Loop, you'll learn about Greek-American culture, and how Greek immigrants helped make Chicago the city it is today! Or, if you want to see some awe-inspiring art, check out the Kavi Gupta Gallery. Inside, you'll find artworks of all shapes and sizes to ponder over. Does it get any more cultural than that? No, it does not. State of the Union Station Want to see one of Chicago's most recognizable landmarks up close? West Loop has you covered with Union Station. Built back in the 1920s, it's the transport hub that brings many out-of-towers into the city. Its Art Deco stylings are so iconic that it's featured in heaps of Hollywood productions. The Untouchables, Catch Me If You Can, Blade Runner, and many, many more have shot iconic scenes in this very building. So go see it for yourself, and snap some sweet pics for your socials because you know you will. Grab a bite Phew, all the doing things and seeing stuff is bound to make you hungry. Thankfully, West Loop has plenty of places to refuel. In the mood for something meaty? Check out El Che Steakhouse for some prime cuts, refreshing drinks, and good times. Prefer your meat between two buns? Give Smyth and The Loyalist a go. Looking for something continental? Hit up avec for some Mediterranean delights. Grab a drink And finally, let's end our list on the drinks menu. West Loop has lots of bars and pubs to drown some suds. Head to Lone Wolf or Haymarket Pub for your craft beer needs, with plenty of local Chicago brews on tap. For some exotic cocktails, give Kumiko a try, which provides a Japanese twist on the usual mixer affair. If you want a variety of spirits, stumble to CH Distillery. And that's our list of things to do in West Loop, Chicago! Enjoy!
Dom Bewley
chicago in may
Blog

Chicago in May

Spring has sprung, and summer is just around the corner. That big yellow ball in the sky isn't so shy anymore. That's right y'all, it's May. Time to shuffle off the light jackets and risk it in just a t-shirt or summer dress. Whether you're hitting the Windy City for a vacation, or a resident wondering how to spend the newfound warmth, never fear! This list caters to you all. Scroll down, and find out what you shouldn't miss in Chicago in May. Featuring: Skydeck Chicago River Cruises Navy Pier funfair Bike rides The Zoo and more! Chicago in May: What to Expect May is when temperatures will start to climb. Generally, you'll find tops of around 68-70°F, or 20-21°C, and dips of around 50-51°F, or 9-10°C. So, pack some lighter clothes for the days, and some warmer jackets and sweaters for the nights. There's a chance of rain too, so pack your best umbrella, just to be safe. Chicago in May: What to Do Skydeck Chicago Looking for thrills, buddy? How about heading up to the 103rd floor and overlooking the city at over 1,300ft? If that sounds like just the ticket, then check out Skydeck Chicago! Formerly the Sears Tower, Skydeck gives you amazing views across the city and beyond. In fact, you can see four different states from the viewing platform! Spot key Chicago landmarks, and if you dare, head out onto The Ledge, a see-through, glass-floored platform. See the city right beneath your feet. Not for the faint of heart, but if you've already made the journey up to the top, why not go the extra step? We dare you. Then, when you're done, ride the Multimedia elevator all the way down to terra firma, and learn about landmarks as you pass them. Shoreline Architecture River Cruise Do you like water? Not just inside your body, but outside too? Does the thought of riding Poseidon's waves while seeing some sweet buildings get you giddy? Well, check this out. Hop aboard a Shoreline Architecture River Cruise and do just that. Chicago in May is the perfect time to catch a ride. The city has heaps of interesting architecture to see, including works from building men like Goldberg and van der Rohe. Plus, you'll learn about the Great Fire in the 19th century that helped shape the metropolis it has become today. Make sure you take some sweet snaps for your social media, so people think you're cooler than you really are. Learning and boats - does it get much better than that? Navy Pier Do you like rides? Are you looking for an exhilarating experience in the city? Then you're looking for none other than Navy Pier. This 50-acre seaside locale is one of the biggest tourism draws in Chicago. Perhaps the pier's biggest attraction is the Centennial Wheel, a colossal Ferris Wheel that towers over the boardwalk. Rising to over 200ft at its peak, you'll get amazing views all the way to Lake Michigan. And, if those pesky clouds show their grey faces, never fear, as each gondola is a closed unit. On top of all that, there are plenty of other rides to try out, bites to eat, and drinks to wash it all down. Pick up a souvenir while you're at it. Stop by the Zoo Why not make the most of the May weather by visiting the zoo in Chicago? Lincoln Park Zoo is a wonderland of animals, with thousands to see and meet. There's the Sea Lion Pool where, shock horror, the sea lions hang out. Or, if you like your mammals landlocked, there's the Center for African Apes, with an assortment of apes and gorillas to see. Then, head into the lion's den at Kovier Lion House, which houses more big cats than you could shake a paw at. Beyond that, you can take a cruise of the South Lake Lagoon, or check out some of the rides. The Lionel Train Adventure is perfect for kids, taking passengers on a trip to explore the surrounding woodland. There's also the Endangered Species Carousel, where riders can hop aboard nearly 50 replicas of endangered animals and help raise awareness of their plight. Then, grab a bite at the cafe, or pick up a stuffed animal for the little one. Bike and Roll Want to see the sights in Chicago, but make the most of the May weather? Then hop on a two-wheeler and get some exercise while you're at it! Hire a bike, and go exploring. Glide beside Chicago's lakefront, discover the city's many trails and green lanes to avoid traffic, and see all the city's wonders while breathing in that great fresh air. Bring some food and a few drinks, find a spot to settle, and put together a mid-ride picnic. A great way to spend a sunny day in the windy city. Play ball If you're a sports fan, you may have heard of the game they call 'baseball.' One person throws a ball, the other hits it with a bat, and then everyone runs around trying to catch it. That about sums it up. Well, if that sounds like you, then you'll be well aware of the Chicago Cubs. A trip to their stadium at Wrigley Field might appeal to all sports fans, as the atmosphere is notoriously infectious. And not in the mask-wearing, 6ft apart way. This century-old ground is home to baseball games throughout the year, so why not check one out and see what all the fuss is about? Get flowery Fancy yourself a bit of a Greenfingers? Then you might be interested in a visit to one of the country's biggest and best botanical gardens! The Garfield Park Conservatory houses thousands of flora beneath its glass dome, and in May, it's the location of the 2022 Spring Flower Show. So if you want to see some award-winning tulips, daffodils, and other flowers you know and love, go check it out! Relax and see the city If you want to give those dear legs of yours a rest, why not hop on a bus and get a tour of the town? A Gray Line Chicago Grand Tour takes you around all of the city's biggest landmarks, including Orchestra Hall, Lake Point Towers, and Lincoln Park Conservatory, all the way to Grant Park. You even have the opportunity to hop off and go exploring at certain points, as long as the bus isn't delayed! And that's everything you need to know about Chicago in May!
Dom Bewley
Navy Pier and Centennial Wheel in Chicago
Blog

Navy Pier thrills: Centennial Ferris Wheel vs Flyover in Chicago

One lifts you above Lake Michigan, the other sweeps you over it; we compare vibes, energy, food spots and more near these Navy Pier favorites.

Have a 5% discount, on us!

Sign up to our newsletter and receive exclusive discounts, trip inspiration and attraction updates straight to your inbox.