Kindle Some Romance On A Sunset Sailing Tour
With a glass of wine in one hand and your camera in the other, soak in the glorious sunset as it reflects off the Chicago skyline on a twilight boat tour.
Choose from a budget-friendly option on a large, shared vessel, or splurge on the ultimate romantic experience with a privately chartered sailboat.
Visit The Chicago Cultural Center
This magnificent building located downtown once served as the citys first public library. The building alone is reason enough to make a visit. Home to the worlds largest stained glass Tiffany Dome, theres a ton of history in the expertly crafted walls of the CCC.
The building was completed in 1897 as both a public library and a civil war memorial and was built with incredible materials such as rare imported marbles, polished brass, mother-of-pearl, and colored stone. The 38-foot-diameter Tiffany dome has over 30,000 pieces of glass and was restored in 2008. Today, it is open to the public seven days a week always free! Frequent exhibitions and public events are also usually entirely free to attend. If you love culture, architecture, and history, this is a great free place to spend your day.
Andersonville Viking Pub Crawl
With temperatures not expected to get out of the 30s this weekend, you’ll have a chance to feel like a real Viking at the fifth annual Andersonville Viking Pub Crawl.
Costumes are encouraged with the best-dressed Scandinavian swashbuckler receiving a special prize.
Tickets are $35 and grant participants a commemorative glass, an appetizer at check in and access to drink specials at over a dozen local businesses.
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Take An Architecture Cruise On The Chicago River
The architecture in the Windy City is unique, historic, and complex, and theres no better vantage point to admire it all than the waters of the Chicago River. As you cruise under the citys skyscrapers, youll pass the East Bank Club, the old Post Office Building, the Willis Tower, and plenty more.
Highlights include the DuSable Bridge, with its decorative posts and impressive engineering Tribune Tower, a magnificent Neo-Gothic luxury apartment complex and the Wrigley Building, a classic skyscraper that serves as a focal point for public life in the Windy City.
You can also take a cruise with the Chicago Architectural Center, which celebrates the towns magnificent designs and historic structures. After visiting the exhibits, you can join one of their tours and admire the buildings in the best possible way on the water!
Tours typically last an hour and a half, and the guides are notably informative and entertaining.
Be Dazzled By The Official Christmas Tree
For more than 100 years, the city of Chicago has celebrated the holiday season by prominently displaying the official Christmas Tree in Millennium Park. Situated close to the intersection of Washington Street and Michigan Avenue, the impressive 55-foot Colorado Blue Spruce is decked out with thousands of twinkling lights. The tree will stay up through Jan. 9, 2022.
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Chicago Bears Vs Miami Dolphins
Coming with some new additions from the trade deadline, the Chicago Bears look to right the ship Sunday at home against the Miami Dolphins.
Justin Fields and company are coming off a blowout loss to the Dallas Cowboys.
If you can’t make it to the game, hang out with former Bear Corey Wootton and FOX 32s Gabe Ramirez at the Miller Lite Brew & View at Nite Games Sports Bar and Grill in Oak Forest.
Kickoff is set for noon at Soldier Field.
Explore Chicagos Stunning Parks
Chicago is no far friend from nature. With its lush parks, riverside excursions, the Lakefront, and incredible hiking trails, the city is abound with opportunities to get back in touch with Mother Nature. These offer wonderful paradises alive with growth and wildlife during the summer heat.
Weve rounded up some of the most celestial secret gardens and parks around Chicago so you can take a look and choose one this summer for a euphoric day out in nature.
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Learn About Latin Culture At The National Museum Of Mexican Art
Nestled within Chicagos Pilsen neighborhood, this free museum provides an exciting, educational insight into Mexican and Latin American culture.
With a collection covering some 9,000 pieces of art spanning from ancient Mexico to present modern times, the National Museum of Mexican Art proudly showcases one of the countrys largest Mexican art collections.
Ice Skate At Millennium Park
In the winter months, Chicago becomes a frozen wonderland with plenty of spots to go ice-skating.
One of the best things to do in Chicago in winter is to go ice skating at Millennium Park right next to the famous Bean!
The parks massive ice skating rink is open from early November to early March, making it the perfect activity for a winter day in the city.
Whats more, admission to the rink is free if you bring your own skates.
If you dont have your own, you can rent skates.
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Grab Some Ice Cream At Original Rainbow Cone
This longstanding Chicago ice creamery hibernates in the winter, but in the summer theyre teeming with elated customers and ice cream fanatics.
Visit the Original Rainbow Cone, choose from cones, milkshakes, sundaes, or banana splits, then burn off the calories with a pleasant stroll through the parks of Dan Ryan Woods.
Explore The Chicago Cultural Center
The Chicago Cultural Center is one of the citys most iconic buildings, and it also happens to be completely free to visit.
Located in the heart of downtown Chicago, this cultural center is home to numerous exhibits and art displays from local artists, as well as plenty of events and performances.
So if youre looking for a free indoor activity thats also great for people-watching and exploring, be sure to check out the Chicago Cultural Center.
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Laugh At The Faces Of Crown Fountain
While far less extravagant than the Buckingham fountain, the Crown Fountain takes the cake in the entertainment department.
Its become famous for its Faces of Chicago element, where anonymous people are projected onto two identical 50-foot towers, appearing as though theyre spitting out a stream of water.
Youll often spot kids running around in the fountain, trying to cool off on those sizzling summer afternoons.
Catch A Show At The Chicago Theatre
Besides sitting down for a show at the world-famous Chicago Theatre, visitors are blessed with the opportunity to go behind the scenes and explore the grand history and intricate architecture of this iconic entertainment venue.
Step on stage, visit the rehearsal space, admire the ceilings, and more, all with an expert guide leading the way.
The theatre is centrally located to countless bars and restaurants, which makes planning the evening outing a breeze.
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Visit The Buckingham Fountain In Grant Park
The Buckingham Fountain is one of Chicagos most iconic landmarks.
Located in Grant Park, this landmark fountain was built in 1927 and has been a popular spot for visitors and locals alike ever since.
Its a sight to behold any time of the day, but its particularly breathtaking during the water show, which occurs every hour.
Come after dusk, and you can enjoy a light and music display on the fountain as well.
The fountain typically runs from mid-April to mid-October, so if you happen to be visiting in the summer period, dont miss this entirely free attraction in Chicago.
Bask In The Glow Of Zoolights
More than one million lights make up the mesmerizing displays at ZooLights at Lincoln Park Zoo. This years family-friendly holiday event, set in the citys historic lakefront zoo, includes brand-new light shows, photos with Santa, and live entertainment. Tickets are $5 online, but admission is free every Monday in December. ZooLights ends on Jan. 1.
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Take A Stroll Along The Citys Famed Magnificent Mile
The Magnificent Mile is one of Chicagos most popular tourist destinations, and for a good reason.
This bustling stretch of Michigan Avenue is home to some of the citys best shopping, dining, and attractions.
It divides two of the best areas to stay in Chicago, Streeterville and River North, so chances are you will be staying somewhere close anyways.
Even if youre not looking to spend any money, the Magnificent Mile is still worth checking out.
There are always plenty of people-watching opportunities, and the architecture is simply stunning.
So whether youre in the mood to window shop or just soak up the sights and sounds of the city, be sure to add the Magnificent Mile to your list of places to visit in Chicago.
Mag Mile is festive in winter read our guide to Chicago at Christmas for more!
Spend An Afternoon At Navy Pier
Chicagos iconic lakefront destination, Navy Pier plays host to renowned restaurants, shopping opportunities, boat tours, and so much more.
The waterfront space was conceived as merely a freight dock, however, its slowly evolved over the last century today, the must-see destination features exhibits, rides, parks, and unbeatable views of the glistening Lake Michigan.
Art and tech fans will find plenty of common ground at Verse: The Art Of The Future, where you can don a VR headset and explore an entirely virtual gallery. And for great views of the real world outside, hop aboard the Centennial Wheel, which boasts commanding views of the skyline from 200 feet in the air.
Countless walking tours pass through the area, which also serves as the main cruise departure point. The Explorer Pass gives you access to the attractions at Navy Pier, plus other 25 attractions and activities in Chicago.
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Catch The Chicago Air & Water Show
Another fantastic free spectacle this summer can be found in the skies above. The Chicago Air and Water Show will return in August to wow spectators lined up along North Avenue Beach and the Lakefront from Fullerton to Oak Street once again. Presented by the City of Chicago it is the largest free show of its kind in the entire country and features a variety of military and civilian performances.
On the 20th and 21st of August the Navy Blue Angels, the Golden Knights Army Parachute Team, and multiple other performers will take to the skies from 10 am until 2 pm. Free on both days, it will be the first full-scale Chicago Air and Water Show since 2019 following a full cancellation in 2020 and a scaled-back version featuring a solo demonstration by the Navy Blue Angels in 2021.
Visit The City Gallery At The Historic Water Tower
For a truly unique experience, head to the City Gallery at the Historic Water Tower .
This free gallery is located in one of Chicagos most iconic landmarks the historic water tower that stands tall on Michigan Avenue.
The gallery itself features rotating exhibits from local artists, and its also a great spot for some photo ops.
And if you happen to be visiting in the winter, the Water Tower is also one of the best spots in the city to see holiday lights.
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Free Festivals And Annual Events
Whether youre a resident or a visitor, you ought to put one of these free events on your calendar.
38. Chicago Blues Festival
This annual music festival features blues legends and up-and-coming artists alike. The Chicago Blues Festival is typically held in early June at Millennium Park and venues across the city.
39. Chicago Gospel Music Festival
The Chicago Gospel Music Festival showcases gospel artists from all over the country, featuring a variety of styles from traditional choirs to hip-hop-inspired gospel. The festival is held at the Jay Pritzker Pavilion in Millennium Park during the summer.
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40. Chicago Jazz Festival
The Chicago Jazz Festival is an annual event that takes place in Millennium Park on Labor Day Weekend. Neighborhood concerts lead up to the festival, held at locations historically significant to jazz in Chicago.
41. Grant Park Music Festival
The Grant Park Music Festival is a series of classical music concerts that take place throughout the summer at the Jay Pritzker Pavilion. Free seating is available to the public.
42. SummerDance in Grant Park
SummerDance is an annual series of music and dancing events that takes place in Grant Park in the summer. In 2021, the festival will be held during August and September in parks throughout the city.
43. Open House Chicago
44. Christkindl Holiday Market
Take A Selfie At Cloud Gate
Weve all seen it pop up on our social media feeds a selfie in front of the Bean is a right of passage for any Chicago tourist.
A quick social media most here one of the most popular things to do in Chicago, no doubt.
The giant bean-shaped mirror weighs 110 tons and sits in Millennium Park, the popular lakefront area in Chicagos downtown Loop.
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Learn About Chicagos History At The Chicago History Museum
The Chicago History Museum is one of the citys most popular museums, and its also one of the most affordable.
This museum chronicles the history of Chicago from its early beginnings to the present day, with exhibits on everything from the citys architecture to its food culture.
It also holds several events and programs throughout the year, so theres always something new to check out.
And best of all, there are free admission days for Illinois residents with valid IDs.
For tourists visiting Chicago, admission to the Chicago History Museum costs under $20, making it one of the best cheap things to do in Chicago.
Stroll Around Navy Pier
Navy Pier is one of Chicagos most popular tourist destinations, and its easy to see why.
This 3,300-foot-long pier offers stunning views of Lake Michigan and the city skyline, and theres plenty to do along the way.
You can ride the Ferris wheel, take a cruise on the lake, or simply wander around and enjoy the sights and sounds of the pier.
Its free to enter, so even if you dont want to spend any money, its still a great place to visit for the views and vibes only.
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Rent A Private Luxury Boat
Deep-dish pizza is an undisputed Windy City icon. Why not kill two birds with one stone on a luxury boat tour that includes its own pie?
On this private pontoon, suitable for 2-6 people, youll glide past Goose Island, the Riverwalk, Willis Tower, the Civic Opera House, and plenty more staying far away from the selfie-stick-wielding crowds of tourists.
Head To The Ernest Hemingway Birthplace Museum
Arguably the most famous American author of all time, the Ernest Hemingway name has since echoed across the globe.
He was born, of course, in Chicago, and keen visitors are welcome to explore the childhood home-turned-museum in which he lived at the turn of the 20th century.
Tours through the museum dive into the life, work, and legacy of the Pulitzer Prize-winning author a must for any literary fan.
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Catch A White Sox Baseball Game At Guaranteed Rate Field
As much as the locals love their deep-dish pizza, that love doesnt quite compare to the obsession with the Chicago White Sox baseball team .
Experience the famous White Sox atmosphere firsthand by catching an MBL match at Guaranteed Rate Field on the citys South Side.
Sports fans can also swing by Wrigley Field, home to the Chicago Cubs. This beloved Major League Baseball stadium is a public institution in the city, and theres no better way to spend a warm day than waiting for a home run in the stands.
Baseball buffs will certainly feel spoiled in the Windy City! The season typically runs from March to October, with concerts, pre-season matches, and events held at the stadium outside of those months.
Visit Lincoln Park Zoo
Visiting Lincoln Park Zoo is a fun and free year-round activity. As one of the only zoos in the country offering free admission, you can explore a free world of wildlife in the middle of the city and experience numerous exciting animal encounters. As well as over 230 species of animals there are often fun seasonal events such as the annual Zoolights. Home to primates, elephants, giraffes, sea lions, penguins, reptiles, and much more, if youre an animal lover, theres no place better for free activities than Lincoln Park Zoo. In summer many animals will be lounging around in the sun so theres no better time to say hello!
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Catch A Game At Soldier Field
For almost 100 years, Soldier Field has been a beloved part of the citys athletic scene.
For football fans, this is hallowed ground, as the home field of The Chicago Bears, who line up at Soldier Field during the season , foster a wild atmosphere and the only way to really experience it is to join in on the action!
And if you prefer the other kind of football , when visiting the Windy City, immerse yourself in that passion by attending a Chicago Fire match at Soldier Field.
Whether you prefer the NFL or the MLS, a day spent cheering in the stands is always a good time!