Sporting Events In Chicago
Sport is definitely one of the Chicago highlights and you can get out and be active no matter the season! Whether you prefer taking part in an activity, or just watching, there are always plenty of options on offer!
Wrigley Field
- First opened in 1914, this is one of Americas most iconic baseball parks
- Home of Major League Baseball team the Chicago Cubs
- Known for its ivy covered home-run wall, its the second oldest stadium in MLB!
If your weekend getaway to Chicago coincides with a baseball game, do your best to rustle up some tickets and soak in the festive atmosphere of Americas favorite pass time! Wrigley Field baseball stadium is located on the north side of Chicago and is easily accessible by public transportation.
Chicagoland Speedway
- Head to Chicagoland Speedway to test your high-speed driving skills and get your adrenaline going!
- Choose between a range of heart-pumping driving experiences
- Set your fastest lap on a real NASCAR speedway!
If your racing addiction demands more than just a seat on the sidelines, check out Chicagoland Speedway! This fun location offer exciting options that will definitely satisfy your need for speed! Get behind the wheel of a NASCAR and take it for a spin on Chicagos NASCAR speedway!
Fame Play Ping Pong at Acebounce
- Challenge your friends to a game, or three of ping-pong
- Work up a thirst, then enjoy some drinks from the on-site bar
- A great social source of fun on a weekend trip to Chicago!
Visit The Chicago Picasso
Yet another opportunity for a spectacular snapshot is located in the Daley Plaza where theChicago Picasso piece was unveiled on August 15, 1967. It was commissioned by architect Richard J. Daley who designed his namesake center in the early sixties.
Although the piece was untitled upon creation and presentation, the sculpture was rumored to represent the French model Lydia Corbett who sat for a series of drawings done by Picasso in the fifties. The sculpture was considered controversial at the time but has become a landmark for the city.
Weekend Cultural Entertainment In Chicago Music/concerts/theatre
Your Chicago itinerary should include some nocturnal fun and the city has plenty of great music and theatre options. Here are three of Chicagos best venues for entertainment!
Green Mill Jazz Club
- A great venue to listen to jazz all night long
- Arrive early, grab a cocktail and settle in for a relaxing evening of free jazz and bebop!
- This was a local hangout for Al Capone and other gangsters during the 1920s
Green Mill Jazz Club in Uptown Chicago is a former speak-easy dating back to 1907. Its the longest continuously running jazz club in the country! Slip into one of the glamorous curved booths and listen sultry singers, big band and bebop! This is one of the most entertaining things going on in Chicago this weekend!
The Hideout
- A great place to go for live music on a Saturday in Chicago
- An intimate prohibition-era bar that host all sorts of live music and dancing
- Check out their line-up on their calendar page
This beloved Chicago hangout has a bar in the front and a stage in the back. It offers a cozy vibe and casual aesthetic. After you find the obscure industrial side-street its hidden on, youll join a welcoming crowd. The outside patio is also used for eclectic music sets, weekly bingo, and comedy and dance nights!
Andys Jazz Club & Restaurant
- Enjoy live jazz music 7-nights a week at this superb venue!
- A lively atmosphere that lends itself well to enjoying live music
- Food is also available at their restaurant
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Trek The Lakefront Trail
All four of Chicagos lakeside City Parks are accessible on 18 miles of a paved pathway shared by walkers, joggers, and cyclists on theLakefront Trail. Some local residents use the trail to get to work while others on the weekends will soak in the Chicago skyline or stroll along the shoreline.
You can also use the path to reach the South Shore Cultural Center, the Shedd Aquarium or the Navy Pier. To get around faster, there are bike rental stations along the way with some offering day pass situations to share these cycles.
A Holiday Classic With A Cirque Twist

Grab your winter coat and get ready to jingle on down to Cirque du Soleil’s brand new holiday spectacular, Twas The Night Before Christmas! You’ll witness their 49th original production, and first ever holiday themed show. Judging by their previous productions, this is one you certainly don’t want to miss!
This unique take on the Christmas classic will bring joy and entertainment to the whole family, whilst teaching the act of kindness behind sharing and the joy of friendship. You’ll also find out what really happens the night before Christmas through Cirques eyes.
So, be sure to spark lasting, magical memories this holiday season with Cirque du Soleil!
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Visit The Top Museums In Chicago
With more than three dozen museums to visit in the city, its hard to know where to start. You might want to begin byexploring this list highlighting dates, times or conditions when you can visit these amazing venues free of charge. This roster also includes the Lincoln Park Zoo which is open to the public year-round without paying for a ticket along with information about the other zoos in Chicago.
Theres also no charge to visit less than traditional locations like the Busy Beaver Button Museum and outdoors at the Chicago Botanic Garden. More classic venues are open for a small charge to cover expenses and donations are always encouraged at the following spots:
Hold Your Event At Navy Pier
Planning a special event in Chicago? Wow your guests with a private event venue unlike any other in the city: Navy Pier.
From weddings to corporate retreats to festivals to trade shows, Navy Piers breathtaking venues and unmatched service provide an unparalleled private event experience, ensuring that no detail goes unnoticed.
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Go On A Sightseeing Tour
The best way to learn about a new city is on a sightseeing tour!
Join our history-loving Chicago-adoring tour guides on foot. We offer pay-what-you-like walking toursevery day of the week in the Windy City.
If youd prefer to enjoy a bus tour, we have a great comparison of Chicagos best. From hop-on-hop-off buses to dedicated tours, youll find one to suit you here.
Another great option if youd like to enjoy a ride is to take a river cruise.
Booze Cruises On Lake Michigan Aboard Anita Dee Ii
Save Booze Cruises on Lake Michigan aboard Anita Dee II to your collection.
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Labor Day On The Mile
As summer comes to a close, check off those last minute bucket list items, and head to The Magnificent Mile! There is no shortage of dining, experiences, or things to do during your three-day weekend. Whether you are visiting for the weekend or live locally, we have rounded up Labor…Read more
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With Full Band Including Sammy Tweedy * Spencer Tweedy * Liam Kazar * James Elkington * Sima Cunningham * Macie Stewart
Thursday, Dec 23
5 & Over // **ALL PATRONS WILL BE REQUIRED TO SHOW PROOF OF VACCINATION IN ORDER TO ATTEND THIS EVENT **
5 & Over // **ALL PATRONS WILL BE REQUIRED TO SHOW PROOF OF VACCINATION IN ORDER TO ATTEND THIS EVENT **
18+ // **ALL PATRONS WILL BE REQUIRED TO SHOW PROOF OF VACCINATION IN ORDER TO ATTEND THIS EVENT **
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Capture The Magic At Buckingham Fountain
For more magical moments to capture on smartphones head over to theBuckingham Fountain in the famed Chicago Loop at the center of Grant Park. Constructed in 1927 from Georgian pink marble, its one of the largest fountains in the world with 200 jets shooting streams over statues more than 25-feet tall across a pool nearly 300-feet in diameter. After the sun sets, lights reflect upon, all around and throughout the water making this the perfect setting for some picturesque photo ops.
The Easiest Way To See The Best Of Broadway

Broadway In Chicago is the source for terrific seats to the most exciting shows in Chicagos bustling Downtown Theater District. On the stages of the James M. Nederlander Theatre, the Cadillac Palace Theatre, the CIBC Theatre, the Auditorium Theatre and the Broadway Playhouse, you will discover theater productions direct from Broadway and world premieres of productions destined for Broadway. Ticket prices for some Broadway shows start as low as $24. Current and upcoming productions include Teatro Zinzanni, Paradise Square, Disneys Frozen, Leslie Odom Jr. The Holiday Concert, Mystery Science Theatre 3000, Pretty Woman, The Play That Goes Wrong, Oklahoma!, Hairspray, The Simon & Garfunkel Story, Come From Away, Moulin Rouge! The Musical, Hadestown, THE SWELL SEASON, SIX, The Prom, Jersey Boys, Fiddler on the Roof, To Kill a Mockingbird, Aint Too Proud, My Fair Lady, The Devil Wears Prada, and Jesus Christ Superstar.
Broadway theater will ignite your night on the town and put you in the middle of the excitement of Chicago tourism. Broadway In Chicago makes it easy to get the best seats available plus provides unique visitor and tourism offerings for a very special theater experience. Go behind the scenes with Broadway In Chicagos Historic Theatre tours. For a truly memorable night at the theatre, be sure to include the luxurious amenities of Broadway In Chicagos Suite Service.
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Other Awesome Things To Do In Chicago This Weekend
So, youre still looking for more fun stuff for your trip to Chicago? Need more Chicago weekend events and attractions? Not to worry, weve got you covered!
Here are 10 more activities, attractions and events in Chicago this weekend!
#1 Get Up Close to the Aquatic Wildlife of Shedd Aquarium
Smart Destinations
Located in the Museum Campus of Chicago along with the Field Museum and the Adler Planetarium, the Shedd Aquarium was once the largest indoor aquarium in the world. This attraction has an incredible diversity of aquatic wildlife from across the planet!
There are freshwater displays with Amazonian animals, oceanic reefs with sharks, tropical fish and corals, touch zones, marine mammals and a plethora of other sea creatures! The aquarium is interactive and educational, its definitely a must-do Chicago weekend activity with kids!
#2 Stop in at the Field Museum
The Field Museum is Chicagos premier natural history museum and one of the largest of its kind in the world!
Founded with an endowment from Marshall Field, it has since gone on to house one of the finest collections of artefacts in the United States. Everything from precious gems to a Tyrannosaurus-Rex skeleton are found here.
Permanent exhibits range from animal dioramas to interactive displays that engage all ages. There are also cultural displays, walk-throughs detailing the planets evolutionary processes, and exhibits delving into cellular-level research and technology!
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Postponed: Juice Box Concerts At The Cultural Center
Head to the Cultural Center with your family of little ones every first and third Friday and Saturdays at 11:00 am-11:45 am for an engaging musical event!
While this will be enjoyable for the whole family, it is geared to kids between the ages of 1-6. See their website for more.
This activity was postponed due to the pandemic and has yet to make a return.
Be sure to check out our post about family-friendly activities in Chicago for a more complete guide.
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Explore The Worlds Largest Starbucks
A good weekend starts with a good cup of coffee, and because Starbucks is turning 50 this year, exploring their unique offerings is the best way to celebrate. Head to the heart of downtown to explore the largest Starbucks in the world: Starbucks Reserve Roastery Chicago, which at five floors is a coffee-lovers playground. Here, all the coffee is roasted onsite daily by Starbucks Master Roasters, and there is a lot more to explore than just specialty brews. Enjoy fresh-baked Italian fare, coffee-inspired cocktails, or try the exclusive nitrogen-infused gelato, and toast to the big 5-0.
Friday, October 1 – Sunday, October 3Chicago TheatreFormer White House Correspondents Dinner comic and Daily Show and Patriot Act star Hasan Minhaj steps out from behind the screen to entertain a roomful of actual humans with comedy and storytelling via his new one-man show, The Kings Jester.Cost: Ticket prices vary
Saturday, October 2Brooklyn Boulders Lincoln ParkAcrobatic yoga, DIY tie-dye demos, a silent disco, and an ice cream truck are just a few of the amenities one can expect when attending this birthday bash from the Lincoln Park outpost of indoor climbing mecca Brooklyn Boulders.Cost: Free for members non-member tickets run $25 per person
Sunday, October 3The PromontoryThis first annual art show and pop-up shop features visual works from community makers plus local business merchants and live DJs. You know what to do.Cost: Tickets start at $5 per person
Know Where To Stay In Chicago
When choosing a place to stay in Chicago, do be mindful of its location as well as its amenities. To get around the city conveniently and to be nearby some iconic Chicago attractions, we recommend downtown or in a central location.
Downtown Chicago is one of the best places to stay in Chicago, for first-time visitors! Its utterly central, houses Chicagos most popular landmarks and is well connected by the citys public transportation system its the perfect base for spending 2 days in Chicago!
The Windy City is huge so and it can be a bit overwhelming trying to choose your accommodation. In case you are in a hurry though, here are three of the best accommodation options we recommend for a great weekend stay in Chicago!
Our Favorite Hostel HI Chicago
- Ideally located right in the city center
- There are options for gender-separated dorms with en-suite bathrooms
This hostel is close to all of the citys top tourist attractions, including art galleries, museums, shops and restaurants. It has over 500 comfortable beds, and offers free breakfast and walking tours throughout Chicago.
- Swanky AF
- With some wicked deco choices!
With this basic, convenient and well-priced studio apartment, you have access to a comfortable, queen size bed, full kitchen, on-site laundry facility, free wifi, and an awesome host who will recommend you places to visit, attractions to see in Chicago.
Our Favorite Budget Hotel Freehand Chicago
Our Favorite Splurge Hotel Warwick Allerton Chicago
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