Fine cuisine, iconic buildings, first-rate shopping, a scenic lakefront, and unique activities by the dozen make Chicago a top destination. Whether you’re planning an architectural tour of Chicago, or mapping out a more eclectic itinerary for you and your friends, these are the awesome influencers to follow on Instagram to inspire your group trip to the Windy City.

Create a unique itinerary by using this pro-tip: peep the feed of Chicago influencers you need to follow before you go. Build out your checklist of activities on Instagram by saving your favourite finds to your own photo collection. This way, when you roll up to your next destination, all your corners are sure to be covered with the scroll of your thumb. No matter which adventures you embark on, make it easy to travel around with your group with one of our bus rentals in Chicago.

An Insider’s Look of the Chicago Food Scene

Chicago Food Authority

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Gimme all the cold yummy stuff @bombobar 😍😍😍😍😍 #chicagofoodauthority

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Famous for its gastronomy, the nation’s third largest city boasts an astounding lineup of restaurants that will have you scrambling to fit far too many food joints into your schedule. The Chicago Food Authority is your ultimate city guide to eating your way around Chicago. Founder Samantha Roby from @sosimplysam serves up the most photogenic food porn, helping you turn those cravings into satisfactory decisions. From local culinary staples to gourmet cuisine, this foodie photographer is definitely your way into Chicago’s mouthwatering food scene.  

Veg Tourist

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It’s #nationalpretzelday and I would like to point out that we did at least get the salad for good measure 😆 Waiting impatiently to dine alfresco again. #vegtourist

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Doting vegetarians will all know that finding a restaurant that caters to their dietary restrictions can be daunting. Thankfully, The Vegetarian Tourist is dedicated to scoping out the best veggie-friendly options in Chicago. Follow her as she shares her delicious findings with food shots that even meat lovers will find themselves drooling over.

Sherrie Savors the City

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💜💜💜It’s good to be back, Chicago. Can’t stop reminiscing all the ube desserts I had in L.A. This rich and decadent Ube Coffeecake is from @bsweetmobile. A bakery specializing in Filipino desserts with a twist. The moist ube cake is doused in a creamy ube sauce. There is so much ube goodness in every bite. Share with me your favorite ube dessert. I want to know! 👇🏼👇🏼👇🏼 #ubedessert #bsweetdessertbar #visitcalifornia #SherrieSavorsLA #SherrieSavorsCalifornia

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While her feed balances savoury and sweet, you can count on Sherrie Tan for your next sugar rush as she showcases all her favourite local eateries and dessert spots. It’s a no-brainer – as the executive pastry chef at Sweet Mandy B’s and one of Chicago’s social media superstars, Sherrie is the purveyor of all things sweet. Take to her Instagram if you find your sweet tooth aching and are in need of a sugary treat to tide it over!

Influencers on Chicago’s most Influential Buildings

Graham Chapman

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🇺🇸🙏🏼 • • • #moodygrams #streetdreamsmag #ig_color #instanyc #newyork_instagram #icapture_nyc #nycdotgram #nycdotgram #ig_nycity #what_i_saw_in_nyc #nycprimeshot #depthobsessed #visualambassadors #illgrammers #agameoftones #master_shots #exploretocreate #hsdailyfeature #sky_high_architecture #hbouthere #newyorker #instamagazine_ #theimaged #streetshared #hsallstars #travelandleisure #livetravelchannel

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Ask anybody and one of the first things they’ll mention about Chicago is its impressive plethora of unique architecture. If organizing your own architecture tour is part of your plan, then scroll through Graham Chapman’s posts before roaming around the city. With his striking photography and his winning #gameoftones, Graham will take you on a tour of the city’s urban landscape by exploring its diverse architectural styles. Acting as a highlight reel to pay homage to Chicago’s unique character, you can expect to find your next stop on his feed, whether it’s a prominent landmark building or a waterfront art deco skyscraper.

Vintage Tribune

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| Scroll through for 4 photos | Every so often Tribune photographer John J. Kim shoots a photo for our “Then and Now” project. It started as a way to showcase the visual changes in the landscapes and people of Chicago by comparing and contrasting historical and present-day photos from Tribune photographers. Usually we’ve focused on images that show great change in buildings or whole city blocks. But this particular set of photos was different. The original photographer, Al Phillips, was sent in 1950 to chronicle new traffic rules on LaSalle Street near Jackson Boulevard (as seen in photos 1 and 3). Phillips took the photos from the Chicago Board of Trade building and wrote down the exact date and time of each of the two frames he took. We know most of the buildings near the Board of Trade are the same today as they were over 60 years ago. We wondered whether there would be an increase in pedestrian and vehicle traffic. The project became a fun challenge for the photographer — and our eyes — when we realized how little had changed. The first and third photos are from 1950, taken from the 9th and 4th floor of the building, respectively. Photos 2 and 4 were taken from the same floors, but 68 years later. Read about how Kim worked to find the exact spots where Phillips stood to take the photos, just 15 minutes apart: https://trib.in/2qRs8cM #vintagechicago #boardoftrade #lasallestreet #thenandnow #thennow #notmuchhaschanged

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Here’s to a different kind of sightseeing: discovering Chicago and its history through old and new lenses. Courtesy of The Chicago Tribune, this feed is a collection of vintage photographs that will have you going back in time and exploring the city’s rich cultural past. For the curious history buffs, track down and visit the locations shown on Vintage Tribune, and witness how certain sites have evolved over time. Who knows which historical secrets you’ll uncover!

Off the Beaten Path: Chicago Art

Chicago Culture Couple

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@Kashink1 | Chicago, IL

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Aside from their name’s sweet alliteration, the Chicago Culture Couple can also revel in the amazing street art that they capture. Their account is your gateway to the public art scene with posts showcasing standout graffiti gems found all over the city. With just a swift look at their feed, inspiration is bound to strike you! Step outside the usual museums and art galleries, and onto the streets of Chicago where atypical art is to be discovered.

Living like a Chicago Local

Nathan Michael

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If you haven’t been to Fulton Market in Chicago, you’re missing out on some of the country’s best restaurants. Thankfully @Chase put together a #SapphireSix guide highlighting the must-see spots (including @LittleGoatDiner). Click the link in my bio to check out the full list. #SapphireOnLocation #Sponsored

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With a discernible taste for the aesthetically-pleasing, Nathan Michael’s Insta feed has it all. Crawling with the coolest coffee shops, the dopest interiors for design fiends, crisp city shots, and inviting meals from top Chicago hotspots, it’s no wonder Nathan quickly reached his tastemaker status. Not only is it visual storytelling at its finest, but combined with his creative signature style and carefully-curated posts, he was able to turn his account into its very own standalone culture guide. All the people commenting and tagging one another on his posts is the very attestation to that!

Sandy Noto

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These are the days we were all wishing for back in February. Eli and I stocked up on summer produce and summer beers and are now ready to laze about in the heat.

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Sandy Noto recently took over CN Traveler’s Instagram stories to share some of her favourite spots in Chicago. With top picks including a stay at the Robey Chicago, a stroll down Lake Michigan, pastries at Cellar Door Provisions, convivial dinner at Roister (Alinea’s casual sister restaurant), and 360 sunset views at the less-crowded Hancock building, your weekend in the city as a local is pretty much all set to go! As a true city connoisseur and professional triple threat (being both a food and travel photographer on top of a gif-maker), Sandy is your go-to source for discovering the people, streets, and buildings that inhabit Chicago. From the best food joints down to city shots that make a drizzly Chicago enviable, it’ll be hard to stop yourself from heading straight to the Windy City after scrolling through her feed.

Feeling inspired to hop on your next out-of-town trip? Check out firsthand what these top-notch influencers are talking and book a charter bus rental for the easiest way to travel to and around Chicago with your group. Get your bus rental quote now!