Traveling To Chicago? Expand That Trip, Get Out Of The Hotel & Experience Chi-Town Like A Local

Glasses of beer on a tasting tray placed on an outdoor table

Work. Travel. Sleep. Repeat.

It’s the way of our modern culture. The hustle lifestyle. We’re lucky to live in a time that’s literally non-stop. Never in the history of humanity have we been able to do business anywhere, at any time. The power of technology. Truly amazing.

What modern tech also propelled us to do is create a new generation of nomads. It’s our basic human nature to explore, to venture out into the unknown. That yearning for more is an innate trait shared among all up-and-coming entrepreneurs.

Not only has our generation been slowly innovating the ideals around where we work, we’re also deconstructing the ideals around what work actually is.

After passing a certain number of flights points you start to understand that with every work trip you take, you have to make the time to collect life’s experiences. Get out and explore, even if it’s just for a few hours after a meeting or during a layover.

The true beauty of life is realized in the moments when we’re unknowing of the future. Where we journey outside our comfort zone and experience the moments that make us, us.

So, the next time you have a layover when traveling for work, don’t sit at the airport bar hacking away on your laptop, head out and explore, meet new people, experience new things.

Next time you’re flying into a new city on a Friday morning, don’t fly out that same night just to get home. Extend your trip to Sunday, and make the most out of it.

No matter where you travel or when you travel, take care of your business first, and then focus on collecting some life-changing experiences.

How To Sum Up Chicago:

Chicago is one of my favorite big cities, no matter if I’m visiting for work or play. It’s the undisputed cultural epicenter of the Midwest. A vibrant urban oasis where there’s always something new happening no matter which neighborhood you’re exploring. And there are lot of them, 77 to be exact, each one is as unique and exciting as the next. If you’re looking for art, it’s everywhere. Interested in letting your inner foodie out? This is your playground. And if you’re a sports fan, who doesn’t love the Bulls or Wrigleyville?

Have 2-4 Hours To Burn? Grab A Quick Bite & Explore The Windy City

If your travel plans for Chicago consist of a long layover, or if you’re being proactive about the possibility of a missed flight, don’t let it get you down. Get out of O’Hare, explore this one-of-a-kind city, and live like a local, even if it’s just for a couple of hours.

Logan Square

If you’re looking for a hip and exciting area to explore in Chicago on a shorter time frame, Logan Square should be at the tippy-top of that list. There’s always new restaurants and bars popping up amongst the young, music going crowd shuffling around Milwaukee Avenue. If sights, sounds, and sustenance weren’t enough, the streets are picturesque and the people are friendly. What more could you want?

Grab A Quick Bite
Close-up of small pies on a tray
Bang Bang Pie & Biscuits

This is mid-Western home cooking at its best ladies and gentlemen. If you have a sweet tooth or if you’re looking for something savory, Bang Bang is a must. The chicken pot pie was a complete surprise. Incredible crust, fresh veggies, absolute hit. As for the pies, what else to say but “bang bang.” The cookies n’ crème and chocolate raspberry were out of this world, and the biscuits looked amazing. They even have pie classes or catering if you’re looking to wow some clients on your next trip to Chicago.

Mini Mott

The Everything Wings are everything, let’s just start off with that. Mini Mott is a fantastic little joint that does a different spin on burgers. It’s definitely not your greasy diner burger, nor is it Au Chaval, but they found their own great little niche and it’s working. While you may not wander here looking for wings, I can’t stress enough, they’re worth a try. Once you’ve had your fill, head down Milwaukee Ave and you’re certain to find something interesting.

Be transported back into the 80’s
Close-up of person thumbing through boxes of vintage records
Brick-A-Brac Records & Collectibles

After you’ve had your mini feast and wandered south through Logan Square, you’ll find yourself stumbling upon this hidden gem of pop culture. If you were a product of the 80’s or just enjoy the entertainment of that period, this place is a must. From records to collectibles to memorabilia, it’s all here. Even if you aren’t interested in buying anything, it’s very much worth the visit to let your inner child out.

Have A Brew...or Two
Close-up of hands pouring a glass of beer from a tap
Revolution Brewing

If there’s one thing the Midwest doesn’t have a shortage of, it’s breweries. And in the city of Chicago, Revolution would be one of the best and the biggest in the bunch. Stop by for an endless selection of incredible beers that are perfected to fit any palate. If you’re looking for mouthwatering eats, their food selection ranges from burgers to brunch specialties. They even have public brewery tours that are a known hit. Do note, the spaces fill up quick so get there early.

Park & Field

This auto repair garage turned restaurant-bar is one of the better outdoor patios that Hyde Park has to offer. In fact, it’s the largest outdoor patio in all of Chicago. You’ll find fire pits, a summer bocce ball league, and a “bags” league, or “cornhole” if you’re not from Chicago. If you’re looking for a hip outdoor hangout with one of the best bottomless boozy brunches on the weekend, don’t miss Park & Field.

Have A 4-8 To Burn? Experience Some True Chi-town Vibes

Finished your meeting early and have hours before your flight? Looking for an interesting place to take your clients? Check out these Chicago gems for some food and experiences you all can appreciate.

Wicker Park

Another one of the quickest growing and biggest hubs for food, drinks, and play throughout Chicago would be Wicker Park. It’s culturally diverse and gorgeous to boot. There are limitless restaurants, bars, coffee shops, and shopping, so killing a few hours here is a pretty simple task.

Grab A Pie, Then Hit The Town
Close-up of freshly baked pizza
Piece Brewery

When most people think of pizza and Chicago, your mind instantly goes to deep dish. But, this New Haven style pizzeria is disrupting that mindset. If you’re a lover of thin crust pizza and craft beers, this is a must-stop for any foodie. It’s a great location to watch some sports or just grab a quick pie and continue to explore the wonders of Wicker Park.

Explore Your Artistic Side
Back of man looking at painting in a museum
Corbett vs. Dempsey

If you’re looking to check out some unique art when exploring Wicker Park, you must make a stop at this amazing little art gallery. Corbett vs. Dempsey specializes in Midwestern, contemporary, and 20th Century paintings, but there’s also a fantastic little record store on the ground floor that can easily expand your exploring time. Once you’ve had your art fix, maybe it’s time to take off and see what else Wicker Park has to offer.

Try A New Game
Bumper car parked with lights and people in the background
Whirly Ball

Let me just preface, Whirly Ball is hilarious. When someone can create a new “game” that includes drinking, they’re certainly innovating. That’s exactly what Whirly Ball has done. They’ve combined bumper cars, lacrosse, and basketball to create a truly unique and fun activity for you, your friends, co-workers, or family. If you’re not into learning something new, there’s also bowling lanes, as well as countless TV’s and beers. It’s safe to say, Whirly Ball has something for everyone.

Bask In Beverage Bliss
Glasses of beer on a tasting tray placed on an outdoor table
The Map Room

There certainly isn’t any shortage of dive bars or craft cocktail lounges lining the streets of Wicker Park. If you’re a beer lover, you must make a stop by the Map Room. It’s a quaint little spot with a massive craft beer selection and it’s almost always packed with locals sipping away. If you’re looking for a low-key beer, and to maybe strike up some interesting conversation with some new people, make the Map Room happen.

Soak Up The Suds
Close-up of small freshly made hamburgers
Small Chaval

After you’ve had a few tasty beverages, you may be wanting something solid to eat. When people think of burgers and Chicago, you’ll always hear of the crowned jewel, Au Chaval. Now, don’t get us wrong, phenomenal burger. But, do yourself a favor, skip the 1-3 hour wait and head to Wicker Park for Small Chaval. Why? Because it’s their sister restaurant, their burgers are out of this world, and the wait is almost non-existent compared to Au Chaval. Thank me later.

Hyde Park

Hyde Park has quickly become one of the hippest and culturally-rich neighborhoods in Chicago, and it’s instantly obvious the second you walk through the beautifully designed landscape. From students wandering about to locals playing games of street chess to the summer crowds heading to 57th street beach, it’s certainly one of the top places to be.

See Some Japanese Gardens
Rock in sand that has been raked with a pattern
The Osaka Garden

If you’re looking for a peaceful and tranquil way to spend a couple hours or even 10 minutes when you’re wandering through Chicago, you have to walk a little south to Jackson Park’s Japanese Gardens. You’ll find an amazing abundance of lush plants and foreign trees that are perfect to calm any racing traveler’s soul. Once you’re feeling zen’d out, go grab some grub.

Go Eat Where Obama Eats
Close-up of vintage diner chair with red cushion and black and white checkered floor tiles
Valois Restaurant

After a relaxing stroll through some historical and artistic parts of Hyde Park, you’ll certainly need to stop for some fuel, or at least a good cup of coffee. When in Hyde Park, you must do as the locals do, and that means eat at Valois. As soon as you step inside, you instantly realize, they pride themselves on being a staple of the community. From Obama’s order being displayed front and center, to walls of murals that celebrate Hyde Park, Valois is certainly a diner that will never go out of style.

Get A Little Beach Time In
Seagull standing on the beach with waves crashing in the background
57th Street Beach

After you’ve had your fill at Valois, if you’re looking to spend some more time outside, and if the day is sunny and warm, you must make your way over to 57th street beach for one of the best spots in the city for some sun-and-sand-time. Grab a towel, some snacks, sunscreen, and take in Lake Michigan like a true local.

Thinking About Extending Your Chicago Trip A Day Or More?

Explore Chicago Like A Local

Like most urban metropolis cities, they take time to get to know and explore. And Chicago is definitely one of those. However, if you have ample time to burn before your next travel date, here are some essential and travel tested experiences that Chicago has to offer.

Have A Laugh
Close-up of a microphone in a dimly lit club
The Second City

If you’re looking to lighten the load of travel, there isn’t a better city in the world for improv or sketch comedy than Chicago. Countless greats in entertainment have all started their comedy careers here, and at any given night you’re guaranteed to see some gut-busting talent. There are literally shows every day, so no matter when you’re traveling to Chicago, you have your pick. Grab some drinks, enjoy some laughs, and who knows, you may be seeing the next great comedian before he or she makes it big.

See A Show
Man playing guitar and singing on stage with man playing keyboard in the background
House Of Blues

When you think of live music and Chicago, the House of Blues should always be top-of-mind. Almost any night, you’ll have the opportunity to see a great rock, blues, or pop band or some fantastic stand-up comedy. Do yourself a favor and escape into the world of music next time you’re visiting Chicago and make the House of Blues happen.

Go Catch A Ball Game
Close-up of a baseball player's hand holding two baseballs

Not only does Wrigleyville host the home of the Chicago Cubs, but there’s also a slew of sports bars and restaurants everywhere you look. If you’re extending your weekend during the long baseball season, and even if the Cubs aren’t your team, it’s still an amazing stadium to watch a game and enjoy America’s pastime.

Enjoy Your Travels To Chicago!

All of us at Speck Travel hope this piece has been helpful in your mission to make the most out of your business travels to Chicago. So, next time you find yourself in CHI, or any city, get out there, make more memories, and take more with you…

If you have any favorite spots in Chicago that we should be writing about, let us know! We’d love to hear from you.

Take your videos, selfies, and pics, and share them with us #TakeMoreWithYouCHI

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