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

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

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1. Architecture River Cruise

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

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3. Art Institute of Chicago

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

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4. 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

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5. Rent a bike

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

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6. SkyDeck Chicago

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

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7. Navy Pier

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

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8. The Great American Lobster Fest at 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

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9. Chicago Jazz Festival

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

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A walker takes in Chicago's fall color
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Chicago in November

Visit Chicago in November and you’ll discover a city preparing itself for the depths of winter but not quite done with fall. Temperatures are generally healthy enough to allow you to still spend plenty of time outdoors, where it’s usually possible to see the last of the fall color or the first flurries of snow. As the days get shorter towards the end of November, there’s also the start of the Christmas festivities to look forward to as well as the celebrations around Thanksgiving on the fourth Thursday of the month. Wondering how cold Chicago is in November and what there is to do? We’ve brought together all the top tips so you need to look nowhere else. Enjoy the end of the fall color Chicago weather in November sees average daily temperatures rise to 50°F, equivalent to a cool spring day. Whilst you’ll want to wrap up warm, do so properly and just eight days of rain will mean you can get out amidst the city’s green spaces to take in the final days of reds, oranges and gold with the turning of its leaves. Should you choose, you could traverse Chicago’s shores on Lake Michigan without ever leaving parkland. A popular pick with those looking to get into the saddle of the city’s rental bicycles – but welcoming to walkers, joggers and skateboarders too – the Lakeshore Trail covers 18.5 miles. Starting at Edgewater Beach in the northern suburbs, it then runs south past many of the city’s top attractions. The first is the free-to-visit Lincoln Park Zoo, whose residents include great apes, big cats, a burr oak older than the city and the Lionel Train Adventure and Endangered Species Carousel rides. Further south lie other major things to do in Chicago in November including the magnificent Field Museum. As one of the largest natural history museums around, it is simply stuffed full of stuffed animals, cultural artifacts from across the globe and the famous skeleton of Sue the T-Rex – one of the most complete and best-preserved examples yet discovered. A short way across the state border, alternative vistas can be sought out at Indiana Dunes National Park. Situated close to the southernmost point of Lake Michigan, the park’s impressive dunes offer a wealth of walking trails, albeit without the fall color. Kick off the festive season Thanksgiving focusses very strongly on Chicago’s downtown areas. Taking place on the grid of streets which form immediately south of the fork in the Chicago River, the annual Thanksgiving Parade is a family-friendly affair which sees State Street taken over by giant helium balloons, dance troops and marching bands. Thanksgiving is also closely associated with the Black Friday sales. Still on State Street, there are a great number of smaller stores, whilst the Magnificent Mile boasts higher end boutiques, department stores including Marshalls and Nordstrom and several shopping malls. If you prefer the artisan touch, look no further than the Chirstkindlmarket that appears in front of Daley Plaza’s 50-foot tall steel Picasso sculpture towards the middle of the month. Its German-style wooden chalet-like stalls are awash with beautiful ornaments, jewelry and tasty treats. Alternatively, you might want to try your hand at another winter staple – ice skating. The city’s largest outdoor rink is the McCormick Tribune Ice Rink that sits beneath the gaze of Anish Kapoor’s Bean, although the Maggie Daley Park Skating Ribbon provides an attraction that’s a little more unusual, with a track winding through the tree cover twice the length of a lap around the Bean’s rink. Savor the views With such a long list of things to do in Chicago in November you shouldn’t forget to stop for a moment or two and take in the windy city in all its glory. One way to do this would be to give your feet a rest by opting for the Hop-On Hop-Off sightseeing bus instead. Taking in sights you might otherwise miss, it also connects up many of Chicago’s top attractions, including the Willis (Sears) Tower. Entering the history books as the world’s tallest building from its topping out ceremony in 1974 until 1998, it continues to host the highest observation tower in the United States – the Skydeck. From its 103rd floor vantage, visitors are able to take in no less than four states whilst feeling the building move in the wind at almost 1400 feet up. Giving the Willis Tower a good run for its money is 360 CHICAGO at 875 North Michigan Avenue. Although its views come from nine stories below the Skydeck, its wrap-around glass windows still have extraordinary panoramas over the city. Get better acquainted with the city’s art Art lovers don’t need to look far in Chicago in November to get a fill of their passion. For one, the city has a huge array of public artworks. As well as the giant sculpture by Picasso in Daley Plaza and Anish Kapoor’s Bean, Chicago also has outdoor works by Joan Miro, Marc Chagall and Magdalena Abakanowicz. The immense Merchandise Mart building comes to life with the world’s largest video installation, projected annually onto the side of the structure from September through November. There’s also an impressive array of murals covering the ends of buildings throughout the city. West Town Street has developed into a mile-long open-air gallery, with other works including the mural of local photographer Vivian Maier in Wicker Park and an unforgettably bright 100 foot image of American singer-songwriter Muddy Waters on North State Street. The pick of the galleries includes the Art Institute of Chicago. One of the largest museums of its kind, the 300,000 objects in its permanent collection spans the genres, ranging from native American textiles to contemporary photography. Making the most of Chicago in November With so much to see and do in Chicago in November you won’t want to waste a second. Skip the lines and save big on admission to many of the city’s top attractions with Go City. Then the only thing left to do is have an incredible time in one of America’s greatest destinations!
Ian Packham
Visitors relaxing in front of the bean sculpture
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Top things to do in Chicago in April

Whilst still chilly, Chicago in April blooms both literally and metaphorically. Its parks are enlivened by the arrival of the first flowers of the spring and the start of the baseball season ensures there’s plenty to keep sports lovers entertained too. Brace yourself though, even its fans would describe Chicago weather in April as indecisive, shifting from days hot enough to swing by the city beaches to those that would drive even the hardiest of urban explorers to the warmth of exhibition spaces such as the Field Museum. On average, you’ll need to be prepared for temperatures ranging between 39 and 57°F. Bring a windcheater as the ‘windy city’ lives up to this moniker in April, although this does blow showers through quickly to leave 13 hours of sunshine a day. Chicago sunny day activities With the sun on your back Chicago in April is the ideal time to explore the city from the water. Although Lake Michigan – the USA’s largest lake – might be your first thought, cruising along the three branches of the Chicago River will reveal much of the city’s history, from the great fire of 1871 to the Willis (Sears) Tower, the tallest building in the world for 25 years and still the second-tallest in the western hemisphere. As a result, its 103 story Skydeck provides unrivalled views, especially from its protruding glass boxes together known as The Ledge. Rated as one of the most walkable cities in America, the architectural landmarks of the city are also eminently explorable by bike. Take advantage of half-day (four hour) bike rental and you can cover much more ground than would ever be possible on foot, with dedicated cycling tracks linking up many of the attractions lining the shoreline, including the Centennial Wheel and other rides at Navy Pier and 31st Street Beach. Grant Park, and its western extension Millennium Park, are also popular spots on warmer days. Often called ‘Chicago’s front yard’ and renamed in honor of President Ulysses S Grant, this 320 acre urban oasis includes several major attractions. Tulips and other bulbs are a major April draw, alongside year-round works of public art including a memorial to Abraham Lincoln, who served Illinois in the House of Representatives before becoming president. Rainy day activities in Chicago Wondering what to do in Chicago in April if the weather isn’t playing ball? Thankfully, Chicago in April has plenty of covered attractions to look out for without having to resort to second best. Occupying an entire city block within Grant Park is the Art Institute of Chicago. Fronted by majestic bronze lions, it is one of the oldest purpose-built museums in the world, having been established in 1879. Amongst no fewer than 300,000 artworks are some of the US’s most important works, including American Gothic by Grant Wood and Edward Hopper’s Nighthawks. Equally grand in outlook is the lakefront’s Shedd Aquarium. Not just for kids, this gateway to the world’s waterways comprises sections recreating the globe’s most important ecosystems, from coral reefs to the poles. Containing 5 million gallons of water, it’s home to around 32,000 individual animals, of which crowd pleasers include the Beluga whales and bonnethead sharks. Only in town for a couple of months, from March through May, the FRIENDS Experience – or ‘The One in Chicago’ – brings the world of Central Perk to The Shops at Northbridge shopping mall on North Michigan Avenue. Twelve rooms from the sitcom are brought to life, alongside memorabilia such as Monica’s purple door, and even a display of Rachel’s changing haircuts – yes, really! One off events in Chicago in April If you thought the city’s culinary scene began and ended with Chicago-style pizza, think again during Restaurant Week – which now lasts for a gut-busting 17 days straight. Participating restaurants put on special fixed-price menus, with multi-course meals available for as little as $40 for a dinner reservation in some of the city’s top picks. For something a little different, why not time your vacation in Chicago to coincide with International Tom Hanks Day? It may have started as a prank in 2004, but today the Saturday closest to April 1 has movie fans meet up to watch the great man’s back catalogue and buy raffle tickets in the hope of winning signed memorabilia, with all the proceeds going to charity. Alternatively, you could book your place at the Chicago Latin Film Festival (CLFF) to participate in deciding who takes home the Audience Choice Award. Each edition screens around 100 movies, with the festival’s emphasis placed on the artistic and educational rather than box office potential, meaning you’ll see movies here you might see nowhere else. Best of the rest Home to Major League Baseball teams the Chicago Cubs and White Sox, visit Chicago in April and you’ll see the crowds returning to Wrigley Field on the northern side of the city and Guaranteed Rate Field on the southern side of the city, providing two opportunities for visitors to take in the vibrancy of America’s national pastime. Author – and Nobel Prize for Literature winner – Ernest Hemingway was a huge fan. Born in Oak Park, now a central park of the city, in 1899 his attractive birthplace is now a museum dedicated to his life and works, with the house set up as Hemingway would have known it during his childhood. The nearby American Writers Museum celebrates the written word in all its forms and genres, and manages to achieve the near impossible in discussing the important role of writers in the history and culture of the entire country through a range of interactive exhibits. Save on attraction admission in Chicago in April With so many things to do in Chicago in April costs can soon rack up. However, it’s simple to take control of your vacation budget and save whilst you’re doing it by opting to travel with Go City. Our passes give incredible saving rates on admission to many of the top attractions in the city, ensuring you can have the vacation of your dreams without the bank statements of your nightmares! Take a look at how former Go City users have fared by checking out @GoCity on Instagram and Facebook, where you can also join in the conversation by adding your own vacation snaps. Don’t forget to smile!
Ian Packham
Santa Claus waving at the Chicago Christmas light switch on
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Things to do in Chicago for Christmas

Christkindlmarkets, snow-covered streets and stunning seasonal light displays means we’ve probably already successfully answered the question ‘should I visit Chicago in December?’. Filled to brimming with festive fun and events unique to the most wonderful time of year, Christmas in Chicago is a period that will bring a smile to the faces of all but the grinchiest of grinches. Looking for things to do in Chicago at Christmas? Look no further than this round up of the very best! What to expect from Christmas in Chicago Part of what makes the city such a fantastic December destination is Chicago’s Christmas weather. Snowy and cold, it’s exactly what many of us want – and expect – from the festive season. Daytime temperatures aren’t all that different to what Santa’s elves will be used to at his North Pole workshop, with highs of 35°F. They regularly drop below freezing by night to averages of 23°F. Clearly, you’re going to want to ensure you’ve packed your woolens. On the plus side, December is the second-driest month of the Chicago year, with just a couple of inches of rain – and up to eight inches of snow. Skies are largely clear, making days sunny and crisp. Another part of what makes Christmas in Chicago so special is the city’s collection of long-held seasonal traditions, discussed in more detail below. Brighten the winter nights with Chicago’s seasonal lights You don’t have to look far in central Chicago to get your fill of Christmas lights once the sun has set over the shores of Lake Michigan. In addition to its Endangered Species Carousel and Lionel Train Adventure rides, Lincoln Park Zoo sparkles with over 2.5 million bulbs, incorporating several scenes that move to music. Head south from the zoo and you’ll soon end up on the Magnificent (or Mag) Mile, which is a blaze of lights adorned to its trees from an impressive switch on festival in the last week of November right through until New Year. Millennium Park in the Loop – part of Downtown Chicago – has been the location of the city’s official Christmas tree since 2015, although the tradition goes back more than 100 years. However, it has to compete for attention with the avant-garde lighting installations that appear at Chicago Botanic Garden at about the same time. The nearby Daley Plaza hosts a Menorah lighting at the start of December – complete with donuts – for anyone celebrating Hanukkah. Grab your chance to do some last minute shopping Daley Plaza is also one of Chicago’s top seasonal shopping locations since it’s home to the city’s German-style Christkindlmarket. Visitors are free to peruse the selection of local sellers, whose stalls are packed with decorations, clothing accessories and their fair share of sweet treats and mulled wine – rather than the Chicago-style pizza you might plumb for at other times of year. The Bridgeport Art Center’s Renegade Craft Fair is another bastion of independent sellers, with around 250 displaying their wares, which range from bespoke pieces of jewelry to stylish household items sure to add a little je ne sais quoi to your abode. Keep your ear to the ground from the end of November, and it’s more than likely you’ll also hear word of the large number of pop-up one day or weekend markets taking place in and around attractions right across the city. Don’t forget about the city’s all-year shopping options in all the excitement of the season. If just one destination is worth mentioning it’s the Magnificent Mile, defined as Michigan Avenue between Oak Street and Michigan Avenue Bridge. Whatever your budget, you’ll find something to suit here, from well-known department stores to luxury brands Burberry and Tiffany & Co. There’s also a branch of Macy’s at Water Tower Place, although many prefer the holiday windows of the historic Macy’s store on State Street. Show off your skills on the ice The start of winter sees a number of free ice rinks appear in the city, including not one but two within proximity to Millennium Park. The first is the McCormick Tribune ice rink nestled beside the steamy windows of the Park Grill restaurant and the stainless-steel Anish Kapoor sculpture known as ‘the bean’ but officially called Cloud Gate at the heart of AT&T Plaza. The second is Maggie Daley Park Skating Ribbon next door. A sort of wide skating track, it winds its way through the park with its backdrop of downtown skyscrapers, past snowy pine trees and outdoor climbing walls awaiting the warmer weather. But if ‘the bean’ has you yearning to discover more of the city’s art, look no further than the Museum of Contemporary Art, whose permanent collection includes around 2,500 individual works by twentieth century greats including Andy Warhol and Jasper Johns. Take in the exhibitions and shows Many of the city’s other museums also get into the holiday spirit. The Museum of Science and Industry – whose rather staid name is contrasted by the hands-on modern attractions within – hosts their annual Christmas Around the World exhibition, which now also includes the winter celebrations of non-Christian cultures from Diwali’s birthplace of India to China’s Spring Festival commemorations. Christmas shows in Chicago are also a big part of the scene in December in the city. One of the biggest hubs for theater in the US outside of New York’s Broadway, companies big and small go all out to wow their audiences, whether that’s through Christmas classics such as performances of A Christmas Carol or the Nutcracker, or newly written plays that will tug at the heartstrings. If people watching is more your thing, and the wintry streets don’t provide the opportunity, you could do far worse than head to nightspots of North Clark Street such as Simon’s Tavern. Often voted as the city’s best bar, it has been serving up tots of its signature glogg (mulled wine) for nine decades. Save on Christmas in Chicago When it comes to winter wonderlands, the US doesn’t get much better than Christmas in Chicago. And when it comes to making the most of your time – and budget – in the city, things don’t get better than Go City. Offering up great discounts on many of the city’s top attractions even over the festive season, travel with Go City and you can save big on entry to attractions you were planning to visit anyway. Now that’s a Christmas gift everyone would surely love to receive!
Ian Packham

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