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A Weekend Getaway in Chicago, IL


Article by Mindy Hargesheimer

Photography by Mindy Hargesheimer

“Chicago, Chicago I will show you around - I LOVE IT!”

YES, Frank Sinatra - I couldn’t agree more! In fact, we recently showed our friends and their kids around Chicago, experiencing literally inside and out all of the iconic, flavorful, and historic destinations this incredible Midwest U.S. city has to offer! So, what better way to inspire others to check this GORGEOUS city skyline off of your travel bucket list than with an easy agenda to follow for A Weekend Getaway in Chicago

Partnering with Choose Chicago provided one of THE most efficient and insightful experiences in planning our group trip's full weekend agenda!

Partnering with Choose Chicago provided one of THE most efficient and insightful experiences in planning our group trip's full weekend agenda! I highly recommend pointing your attention to their wealth of local guides to 'find your Chicago style' as well as 'see the latest' on only-in-Chicago finds, exploring like a local, and finding what's new and trending.

As a Kansas-residing family, we originally lived in downtown Chicago as well as the Northwest suburbs before relocating to Kansas City, after spending 13 glorious yeas in “the windy city.” Relocating kid #1, and then adding a second to the brood, we never miss a few trips a year back to Chicago to spend quality time with our beloved family still there. 

But, it’s easy to push aside all that this city has to offer that is categorized as “touristy.” So, it’s always refreshing and fulfilling circling back to spending 3-4 days downtown, walking 25+ miles and riding a countless number of city blocks via the El, scooters, bikes, tuk tuks, and via car on Lake Shore Drive. 

I rounded out our 3-day, 3-night agenda that is easy to replicate and a sure-fire way to soak up the entire experience Chicago offers for an unforgettable Midwest getaway.

Be sure to visit @choosechicago for a deeper dive into additional things to explore, places to stay, and events that are updated regularly.

*For additional photos on these destinations, visit @kansascitybucketlist on Instagram 

The Net Out:

Who: 11 travelers / 3 Families

Travel Resource:

Duration: 3 days + 3 nights + driving time

When: Sep 3-7, 2022

Hotels: 21c Museum Hotel Chicago in River North (2 nights), Loews Chicago Hotel in Streeterville (1 night)

City Transportation: Chicago Transit Authority

Millennium Park:

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—--> Day 1: 

21c Museum Hotel Chicago: Hotel Stay | Located just steps from the famous Magnificent Mile shopping district in River North Chicago, contemporary art surrounds and inspires you at. Discover a new kind of cultural and travel experience in the Windy City with this multi-venue museum and 297 room boutique hotel. @21chotelchicago

Shedd Aquarium: Aquarium Tour | Discover the wonder of the aquatic animal world. @shedd_aquarium

Kim & Carlo’s Chicago Style Hot Dogs: Lunch | Kim and Carlo's Chicago Style Hot Dogs has been around since 1995 and is now one of the last remaining hot dog stands in the city of Chicago. @kimandcarloshotdogs

The Original Rainbow Cone Ice Cream Truck: Sweet Treat | Chicago’s Favorite Ice Cream Since 1926.@theoriginalrainbowcone

The Field Museum: Natural History Museum | Since opening the Museum in 1894, our collection has grown to nearly 40 million artifacts and specimens from over 4.5+ billion years of natural history. @fieldmuseum

Lou Malnati’s Pizzeria: Dinner | Serving legendary Chicago deep dish since 1971! @loumalnatis

21c Museum Hotel Chicago:

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Shedd Aquarium:

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Kim & Carlo’s Chicago Style Hot Dogs:

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The Original Rainbow Cone Ice Cream Truck:

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The Field Museum:

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Lou Malnati’s Pizzeria:

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-----> Day 2:

Starbucks Chicago Reserve Roastery : Coffee & Breakfast | A multi-sensory destination of epic proportions, the Chicago Roastery is five stories of coffee theater. Both workshop and stage, it is a three-dimensional window into the coffee journey. It’s an honor to share this immersive experience with you in Chicago. @starbuckschicagoreserve

The Magnificent Mile / Michigan Avenue: Retail Shopping | The Magnificent Mile is a spectacular showcase of style, flavor, entertainment and fun. With more than 460 stores, 275 restaurants, 60 hotels and unique entertainments and attractions packed and stacked along its length, The Magnificent Mile has an indulgence for every passion and every pocket. @themagmile

IT’SUGAR Candy Store: Candy Shop | IT’SUGAR isn’t just candy--it’s an experience. With a unique blend of sugar and pop culture, IT’SUGAR pokes fun at the rules and wants to help the world not take itself too seriously. IT’SUGAR--You Know You Want It. @itsugar

Colores Mexicanos: Shopping | Colores Mexicanos is Chicago's vibrant Mexican gift shop, full of authentic, handmade art, decor, jewelry, and other cultural treasures! @colores_mexicano_chicago

Garrett Popcorn Shops: Treats | Chicago tradition since 1949. Garrett Popcorn is made fresh daily with quality ingredients. @garrettpopcorn

Portillo’s: Lunch | Home to America's favorite Chicago-style hot dogs, Italian beef, burgers, salads, and chocolate cake. @portilloshotdogs

Navy Pier: Entertainment | Navy Pier is where you go in Chicago for events, free public programs, attractions, culture, dining, shopping and more. It's where fun lives large, whether you're a visitor or local, with family or friends. @navypierchicago

Offshore Rooftop: Dinner & Drinks | Offshore is a bright and airy rooftop bar open year-round on the third floor at the East end of Navy and the world's largest rooftop. @offshorerooftop

Starbucks Chicago Reserve Roastery:

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The Magnificent Mile / Michigan Avenue:

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Colores Mexicanos:

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Navy Pier:

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Offshore Rooftop:

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-----> Day 3:

Loews Chicago Hotel: Hotel Stay | Experience Chicago from the heart of the city. The luxurious Loews Chicago Downtown Hotel, situated steps from Navy Pier, offers guests spectacular city skyline and lake views, while enjoying the comforts of home. Our top-rated luxury hotel in Chicago. @loewschicago

360 Chicago: Entertainment | Home of TILT, @cloudbarchicago and the BEST views in #Chicago at John Hancock Center, 94th Floor. @360chicago

Wendella Boats: Chicago River & Lake Cruise | Chicago's Original Narrated Boat Tours. @wendellaboats

Chicago Cubs @ Wrigley Field: Major League Baseball Stadium | Known for its unique traditions and charm, Wrigley Field, which was built in 1914, has been the beloved home of the Chicago Cubs for more than a century. @cubs

Lincoln Park Zoo x The Honeycomb: Family-Friendly Zoo and Nature Boardwalk | In a city where skyscrapers are built every day, Lincoln Park Zoo is dedicated to being the place in Chicago for all things wildlife—where children learn to love animals, where adults rediscover what it’s like to wonder, and where nature isn’t just an escape, but the priority. @lincolnparkzoo 

Sweet Mandy B’s: Cupcake Shop | Serving Old Fashioned desserts in Lincoln Park & Streeterville. @sweetmandybs

RPM Italian: Dinner & Drinks | The sister restaurant to RPM Steak and RPM Seafood, RPM Italian marks the first collaboration between partners RJ, Jerrod and Molly Melman of Lettuce Entertain You Enterprises and celebrity couple Giuliana & Bill Rancic. @rpmitalian 

Chicago Riverwalk: Urban Riverpath | The Chicago River is a treasured natural amenity in the urban canyon of world famous architecture and the Chicago RiverwaIk allows a close proximity to the waterway. The continuous path from Lake Street to the lake front also allows a vertical connection from Upper Wacker Drive down to the waterway. @chicago_riverwalk

Art on theMART: Outdoor Public Art | The world’s largest permanent digital art projection on view nightly in Chicago at 9:00 and 9:30 p.m. @artonthemart 

Loews Chicago Hotel:

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360 Chicago:

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Wendella Boats:

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Chicago Cubs @ Wrigley Field: (photos by Brad Telker)

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Lincoln Park Zoo x The Honeycomb:

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Sweet Mandy B’s:

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RPM Italian:

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Chicago Riverwalk:

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Art on theMart:

And that's a wrap! Chicago, Illinois is another mecca for Midwest magnificence!

Additional ideas for experiencing some of Chicago's best and most iconic destinations and experiences not pictured here include:

Willis Tower

Chicago Theater

The Second City

The Art Institute of Chicago

Museum of Contemporary Art Chicago

Museum of Science and Industry

Adler Planetarium

Maggie Daley Park

Oak Street Beach

North Avenue Beach

Goose Island Beer Company

Chicago Sports Museum

Soldier Field

Chicago Bears

Chicago Blackhawks

Chicago White Sox