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Thursday, September 21, 2023

To Do In Chicago This Weekend

Best Romantic Things To Do In Chicago

impulsively going to CHICAGO for the weekend *GIRLS TRIP*

Chicago, Illinois, is an amazing city to visit, offering a diverse selection of museums, tours, date ideas, and Italian, and other restaurants. Enjoy a birds eye view from 360 Chicago or the Skydeck, spend an afternoon at the Art Institute of Chicago, explore the famous Millennium Park, listen to an orchestra performance, and go for a romantic walk in one of the beautiful parks. Certain attractions may be temporarily closed or require advance reservations. Some restaurants are currently offering pickup only. Hours/availability may have changed.

Admire Art At The Mart

While strolling along the Riverwalk in the evening, be sure to walk along the south side of the Chicago River so that you can see a newer art installation called Art of the Mart.

It is a series of non-sponsored projections on the side of a historic Chicago building called the Merchandise Mart.

Find out more from their website, Art at the Mart.

Learn About Architecture At Frank Lloyd Wrights Home And Studio

As a noted visionary of American architecture who started his career in Chicago, Frank Lloyd Wright is a treasure to the city.

He designed more than 1,000 structures in his lifetime, many of which still stand in Chicago to this day.

Theres no better way to get an in-depth view of his achievements than by touring his home and studio in Oak Park.

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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.

Feel The Thrills Of Indoor Skydiving

Things to Do in Chicago This Weekend  NBC Chicago ...

If youve always dreamed of skydiving but could never muster up the courage to freefall from a plane, iFLY Chicago has the perfect solution.

Nestled in Chicago-Lincoln Park, this adrenaline-pumping activity delivers that wind-in-your-face feeling without all the nerves.

Its significantly cheaper than traditional skydiving, and the ideal stepping stone to the real thing.

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Take A Selfie At The Bean

There are so many unforgettable sites to see in Chicago its hard to single one out but theres one at the AT& T Plaza Millennium Park thats definitely worth a visit. The anchor piece of this stunning park is the Cloud Gate public sculpture erected in 2006 by renowned artist Anish Kapoor.

Also known asThe Bean, this enormous rounded arch is decorated with 168 highly reflective seamlessly joined stainless steel plates measures 33-feet high, 42-feet wide, 66-feet long and weighs around 110 tons. Its become an emblem as a part of the 21st century Chicago landscape and a popular backdrop for selfies.

Columbus Day Weekend: Best Things To Do In Chicago This Weekend With Kids: Scarecrowspumpkinsparade

Looking for the best things to do in Chicago this weekend? Here are some family-friendly events and activities to add to your list for this weekend.

The weekend formerly known as Columbus Day weekend now celebrates a variety of cultures throughout Chicago. If you can get around town with street closures for the Chicago Marathon, you can celebrate Italian Americans at the Columbus Day Parade, Hispanic Heritage Month at Humboldt Park’s Culture Jam, and Czech and Slovak culture at Cicero’s Houby Day.

With the approach of Halloween, it’s a good time for The Great Highwood Pumpkin Festival and Navy Pier’s Harry Potter Halloween Party. Your pet can also test-drive a costume at the Brookfield Zoo’s Boo at the Zoo . There are illuminated pumpkins to peep at Navy Pier and Goose Island, pop-up pumpkin patches to explore at the Cosley Zoo and Indian Boundary Park, and even glass pumpkins to admire at the Morton Arboretum, in addition to a cute Scarecrow Trail. Over 100 handmade scarecrows will be on display at this weekend’s St. Charles Scarecrow Festival, or if you’re looking to build your own, visit Long Grove’s DIY Scarecrow Day.

And that’s just the start of a long list of fall fun things to do this weekend in Chicago with kids. Good thing there’s an extra dayyou’ll need it. Looking for more things to do with kids? Don’t miss our ever-expanding event calendar and our roundup of Free Things to Do This Fall with Chicago Kids.

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Visit Buckingham Fountain In Grant Park

After exploring Navy Pier, head to Grant Park, another of Chicagos excellent downtown parks. Here youll have the chance to explore a huge area of green space, complete with monuments, statues, and a great lakeside walkway. At the heart of Grant Park, youll see Chicagos most famous and beautiful fountain: Buckingham Fountain

Buckingham Fountain is at the center of Grant Park and is a great place to sit and enjoy a coffee or picnic. The fountain itself is beautiful, but it is made even better by the great Chicago skyline in front of you, and Lake Michigan behind.

Further South in Grant Park youll find three other excellent Chicago sightseeing spots to consider adding to your 3 day Chicago itinerary:

Field Museum, Shedd Aquarium + Adler Planetarium

On the south side of Grant Park are 3 beautiful buildings, each of which houses an awesome adventure. The Field Museum is one of the largest natural history museums in the world and is home to some of the best exhibits you can possibly imagine. When we visited in the past, the dinosaur exhibit left us astounded, as they had a full-size Tyrannosaurus Rex named Sue!

The Shedd Aquarium is a world-class aquarium located just east of the Field Museum on Lake Michigan. This aquarium is stunning both from the outside and inside and offers hours of exploration as you make your way through the grounds.

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.

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Listen To Live Blues At Buddy Guys Legends

Established by Grammy-winning Blues music maestro, Buddy Guy, this venue holds a special place in local hearts.

With live performances happening every day of the week, soaking in some of the best blues the city has to offer couldnt be easier.

The menu serves up tasty New-Orleans-inspired dishes, the bar is stocked to the brim, and you can even grab a t-shirt souvenir on the way out!

Visit A Christmas Tree Farm

One of the other fun things to do over Thanksgiving weekend is to head to a Christmas tree farm in the Chicago area to pick and cut your own Christmas tree. If you dont want to cut the tree yourself, you can simply enjoy the surroundings, take a souvenir photo and buy a new pre-cut tree. Most Christmas tree farms open seasonally on the Friday after Thanksgiving, but some will open on Thanksgiving Day. So, be sure to check the farms opening schedule before you go!

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Interact With The Exhibits At The Museum Of Science And Industry

Showcasing an array of interactive and immersive activities, the Museum of Science and Industry is a fun, engaging, and informative day out for the whole family.

Headlining the incredible list of innovation and engineering-themed attractions are the mirror maze, 40-foot tornado simulator, and authentic German submarine.

It sits in the middle of Jackson Park, a perfect slice of nature to dive into a pre- or post-museum picnic.

Trek The Lakefront Trail

13 Actually Fun Things to Do in Chicago This Weekend ...

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.

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What Is The Best Time To Visit Chicago

Chicago gets extremely cold in the winter months. Duh! Everyone knows that by now. Locals will repeatedly tell you winters are cold but summers are amazing! Guess thats why they havent all fled the city. The reward of summer outweighs the cold of winter. I have officially traveled to Chicago every season and can confidently tell you the best time to visit Chicago would be July through October.

OK June is good too but heres why I think July is even better. . .

In July, though humid, you have the Taste of Chicago which is a 5-day celebration of food! Sample the diverse array of local cuisine, dance to live musical performances, and join in on the many activities. Its only the worlds largest food festival no big deal.

August brings another world-famous event Lollapalooza. A music festival featuring over 170 artists on 8 stages with food, drinks, and activities galore. I just realized I say galore a lot. Is that word even cool anymore? Oh well, galore.

Following the beauty of Summer, comes the beauty of Fall. The leaves change into gorgeous colors.

Fall time is the best time! I mean, look at this! These leaves are gorgeous!

If youre looking for incredible photo ops, Fall is without a doubt the most beautiful time to visit Chicago.

Go On A Jet Ski Safari On Lake Michigan

If youre searching north of Downtown, head to Jet Ski Chicago by Lincoln Park.

If youre hunting south of Downtown, they check out Chicago Water Sport Rentals at the 31st Street Harbor.

Either way, once youre saddled into a roaring jet ski on the open waters of Lake Michigan, youll be grinning ear to ear.

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Know How To Get Around In Chicago

Walking is a great way to explore Chicago and a lot of the best places to see are conveniently located in the central downtown area. Most Airbnbs in Chicago are also located centrally.

However, Chicago is a big city thats spread out over a large area so walking between the various neighbourhoods can be very time-consuming.

For moving between Chicagos neighbourhoods, there is a vast network of public transport options. The L Train has stations all over Chicago and is a great way to explore the city! There is also an army of efficient buses that connect the train stops to most Chicago points of interest.

If you dont fancy spending time on the public transport system, then bicycles are a great option! There are a few bike rentals in Chicago as well as the citys bike-sharing system known as Divvy Bikes with bases around the metro stations

The Divvy bikes are an easy and affordable way to get around, especially over a weekend in Chicago. Plus, its probably one of the most fun you can have while visiting Chicago!

Suspect Accused Of Robbing Ride

A weekend in Chicago filled with eating, shopping & more!

The Chicago Auto Show returns to the city this weekend for the first time in more than a year, after taking a hiatus due to the coronavirus pandemic.

The Auto Show will take place this weekend through Monday, shorter than the usual nine-day run that takes place in the winter. It will also be held both indoors and outdoors for the first time since it started in Chicago in 1901, officials said.

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Visit The City Of Chicagos Christmas Tree

If youre in Chicago, you should visit the City of Chicagos Christmas Tree. It is considered one of the citys biggest and brightest holiday traditions. This huge and beautiful tree will light up the center of the iconic Millennium Park, decorated with twinkling lights and making a wonderful backdrop for the city. This is one of the best things to do in Chicago on Thanksgiving you cant miss!

Friendly Reminder: Always Confirm All Details Before Heading Out

Chicago On The Cheap does its best to verify every item published and strives for 100% accuracy. However, due to Covid hours and events change or are canceled, locations close, prices change without notice, errors may occur, etc.

To keep up with the latest news on deals, discounts and free events in Chicago, sign up for the daily Chicago on the Cheap newsletter. and

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Go Ice Skating At The Skating Ribbon

Ice skating is also an interesting addition to the list of things to do in Chicago on Thanksgiving. Before dinner, bring your family and friends to ice skating, an extremely fun game on Thanksgiving.

There are several places to go ice skating in Chicago during the holiday season. One of the most perfect and beautiful places to go ice skating at Maggie Daley Park. It is known for its unique Ice Skating Ribbon, which curves and swerves through the quaint park.

Stroll Along The Chicago Riverwalk

35 Amazing Things to do in Chicago This Weekend

TheCity of Chicago continues to expand on its phenomenal feat of urban planning when constructing The Riverwalk along this namesake waterway running through the downtown district. While traversing this trail, visitors are treating to stunning artwork like a number of smaller colorful graffiti panels or the large-scale installation of Ellen Lanyons Gateway presentation showcasing the story of Chicago on 28 ceramic tile murals.

Options to travel on the river itself include water taxis, taking a boat tour, tackling a journey in DIY mode on an urban kayak or cycle boat. Many riders take Chicagos floating taxis to travel from one waterfront tourist location to another.

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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.

Alternatively, head to Wrigley Stadium to catch the Cubs in action, an absolute must when it comes to things to do in Chicago.

The season typically runs from March to October, with concerts, pre-season matches, and events held at the stadium outside of those months.

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