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Things to do in Bridgeport, Chicago

By Dom Bewley

Heading to Chicago this year? Check out Bridgeport. This seaside district of the city has some great entertainment, from cultural shots to tasty bites. Read on and discover our picks for the best things to do in Bridgeport, Chicago!

Including:

  • Chicago Maritime Museum
  • Parks
  • Bridgeport Farmers Market
  • Bridgeport Art Center
  • Tasty bites
  • and more!
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Sea Culture

Given Chicago's penchant for the sea, it's no wonder the city has a long history of seafaring. For centuries, traders used boats to shop their wares, crossing the great lakes to smaller settlements to make some coin. But don't take us for our word; go and discover this history for yourself at the Chicago Maritime Museum!

You'll find over 6000 artifacts to see, read, and explore, including nautical gizmos from hundreds of years ago, models of ships used back then, as well as images, text, and other displays that detail Chicago's rich nautical history. See how sea travel and trade made Chi-Town the city it's become, and how even today, Chicagoans rely on boats and ships to make it great. For those of you with a passing curiosity in local history, or lovers of boats and the seven seas, this is easily one of the best things to do in Bridgeport when you visit Chicago!

Park your buns

Let's swap the open ocean for some dry, firm land, shall we? If you're looking for a little green space to take a load off, then Bridgeport's got you covered. Palmisano Park used to look somewhat different from its green and pleasant present. For over 130 years, it was a quarry, and when the quarry shut down, the big quarry-shaped hole was used to dump waste. Brilliant. Thankfully, the waste was covered up, and a park was put up on top of it! Now, you can walk around above it all, and see a fishing pond, do laps on the track field, take a picnic on the grass, or simply admire the amazing views of the city!

And right next to Palmisano Park is McGuane Park, which has a host of facilities for the athletic types reading this. Head there, and you'll find a big indoor pool, a gym, baseball fields, tennis courts, and even a playground for the little ones!

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Art for you

Do you like art? Do you like supporting the local scene? Do you want original pieces that your friends and family will envy forevermore? Well, head down to the Bridgeport Art Center! Myriad artists work there throughout the year, creating exciting pieces. However, every three weeks, they open the space to the public and let visitors explore their works, and even buy them if they want. So, if you're in the market for some unique art, head down there and beat the competition with your money.

Market Life

Looking for a little fresh produce for your Airbnb, or simply looking for something tasty to munch on? Just outside the Bridgeport Art Center, you'll find the Farmers Market, right in the adjacent parking lot! Head there on Saturday between 7-11 am, and you'll find a wealth of fresh, locally-sourced produce that'll make your dishes delightful.

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Get your eat on

If you prefer your meals cooked by great chefs and served by excellent staff, then no matter. Bridgeport has some amazing restaurants to sate your hunger.

If you like birds of the quacking variety, then go check out the Duck Inn. This cozy, retro eatery puts a DuckTales twist on American favorites. Duck hot dogs, rotisserie duck, alongside non-duck-related greatness like pasta and fried chicken. No matter your cravings, trust they'll be fulfilled at the Duck Inn; it's one of the best things to do in Bridgeport when you visit Chicago!

Or, if you're in the mood for some Asian deliciousness, hit up A Place by Damao. This traditional Asian cuisine from the Szechuan province of China, pairs national classics like dumplings, noodles, and braised duck, with different levels of spice. Simple but satisfying, go check it out if you like a little heat with your food!

Let's end our food journey on bread. Fresh bread is likely a gift from the gods, handed down to man back in ancient times. Probably. If you want the freshest, best bread in all of Bridgeport, head to Bridgeport Bakery. Whether you're picking up a fresh loaf to make your own, in the market for fantastic bacon buns, or looking for something sweet like donuts or pretzels, they've got you covered!

Cool off

Want to wash all the food down with a few beers, or looking for a destination for your night out?

Looking for a sports bar with some delicious, affordable beers on tap? Try Mitchell's Tap. It's a White Sox bar, but even if you don't support the local greats, you'll still be welcomed with open arms. They have some good local brews in the pipes, as well as some international drops like Belgium's Delirium.

If you want to supplement your night out with a spot of live music, go check out Bernice's Tavern. Inside, you'll find a mix of local lagers and beers, spirits, and bar snacks, along with weekly acoustic sets and open mic nights. A no-nonsense bar for a no-nonsense night out.

And finally, for the gentrified sort, there's Maria's Packaged Goods. With a name like that, you may already know what to expect. Artisinal cocktails, microbrews with kooky names, and a laid-back atmosphere where vintage hats are all the rage.

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Splash the cash

Let's end our list with some shopping, shall we? Bridgeport had a great alternative shopping scene, so if you're looking for bits and bobs, old tech, or collectibles, it'll be right up your street.

Let's Boogie Records and Tapes is your classic alternative music shop, where you can find older, unknown LPs alongside modern underground band releases. Just make sure you have a record or tape player, because the name doesn't lie. That's what they do.

Or, if you like collectibles from across the globe, check out Monster Island Toys. They specialize in all things Godzilla, from classic Japanese action figures to modern comics and everything in between. But you'll also find other figures from pop culture are represented too. So, if you're a collector, or looking to pick up a gift for your little one, stop by and see what's on offer.

And that's our list of the best things to do in Bridgeport, Chicago!

Dom Bewley
Go City Travel Expert

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Things to do in West Loop, Chicago

Head to Chicago for your vacation and want to know what's good? Give West Loop a try. There's so much to do and see, you might never leave. Here's our list of the best things to do in West Loop, Chicago. Including: Street Markets Park walks Go bowling Get cultural Try climbing and more! Get Marketeering Let's start this shindig with a smattering of shopping. West Loop has an abundance of markets where you can pick up anything from fresh groceries to hand-crafted jewelry. If you're looking to wheel, deal, and shave a few bucks off your purchases, head over to Randolph Street Market. In the summer months, you'll find over one hundred vendors taking over the Chicago Journeyman Plumbers Union Hall parking lot. Within this bizarre bazaar, you'll discover stalls filled with antiques, old records, hand-crafted wonders, and other assorted knickknacks. Or, if food is your purchase of choice, give Chicago's French Market a go. You'll find myriad stalls with fresh produce from all corners of the world, and a host of pop-up restaurants and bakeries selling delicious bites. Rolling down the lanes Do you like balls? Do you hate pins? If you answered yes to both of these questions, this next entry will be for you. Punch Bowl Social has taken over West Loop. Their demands? Maximum fun. Their plan? 30,000ft of retro arcade, karaoke, fine dining, and more bowling lanes than you could shake a used pair of shoes at. Grab a drink, collect some fellows, and go throw some bowling balls down some bowling lanes to drop some bowling pins. It doesn't get much simpler than that. Then, when you're all bowled out, check all the other entertainment on offer, or grab some classic diner food from the on-site restaurant. Yee-haw. It's bowling time, or something. Park Life If the weather is good and you're so inclined, head to a park for a jolly good time! Thankfully, West Loop has some great green spaces, so if you're visiting Chicago, get that green in you. Perhaps its better-known park is Union Park, where the annual Pitchfork Music Festival brings farmers from all across America to get angry at things. Not really, it's a music festival, and a good one at that. However, if you don't make it in July, there's still loads to do. Pools to jump in, courts to play in, and that sweet grass to relax on. Or, if you want to entertain the little ones, stop by Mary Bartelme Park. It has an amazing children's playground with unique and exciting play equipment you won't find anywhere else. It's also good for dogs, if your little one walks on four legs. The Climb Picture the scene. You're a secret agent, climbing up a rocky cliff face. You receive a call on your sweet futuristic sunglasses. It's your secret spy agency, and they have a job for you. You choose to accept it, and throw the glasses off towards the camera as they self-destruct. Yeah! So if the climbing part of that interests you - and nothing else - head on over to Brooklyn Boulders. There, you'll find lots of surfaces to climb, which is what you want. If you're a seasoned pro, feel free to hit the walls and do some sweet flips, or whatever climbers do. If you're new to the climbing game, never fear. They have expert trainers on hand to teach you the tricks of the trade. And who knows, maybe they're secret agents too. Hiding in plain sight, at Brooklyn Boulders. Would you like to play a game? If you go to sleep listening to the distinctive cling of pinball tables and assorted beeps and boops of old arcade machines, you might like this next place. Take a running jump into Emporium Arcade Bar and fall into a world of old-school arcade action. With a slew of pinball-flicking, foosball-spinning, puck-slapping, and pool-shooting fun, it's a lovely place full of joy and smiles. If you have friends, bring them with you, and pump the fun up to stratospheric levels. After you've spent all your money on machines, take out a loan and go enjoy a refreshing cocktail or IPA at the bar. You will love it. Won't you? Yes. Culture! If all of that wasn't fun enough for you, how about a little learning and culture to take that fun factor to the next level? At the National Hellenic Museum in West Loop, you'll learn about Greek-American culture, and how Greek immigrants helped make Chicago the city it is today! Or, if you want to see some awe-inspiring art, check out the Kavi Gupta Gallery. Inside, you'll find artworks of all shapes and sizes to ponder over. Does it get any more cultural than that? No, it does not. State of the Union Station Want to see one of Chicago's most recognizable landmarks up close? West Loop has you covered with Union Station. Built back in the 1920s, it's the transport hub that brings many out-of-towers into the city. Its Art Deco stylings are so iconic that it's featured in heaps of Hollywood productions. The Untouchables, Catch Me If You Can, Blade Runner, and many, many more have shot iconic scenes in this very building. So go see it for yourself, and snap some sweet pics for your socials because you know you will. Grab a bite Phew, all the doing things and seeing stuff is bound to make you hungry. Thankfully, West Loop has plenty of places to refuel. In the mood for something meaty? Check out El Che Steakhouse for some prime cuts, refreshing drinks, and good times. Prefer your meat between two buns? Give Smyth and The Loyalist a go. Looking for something continental? Hit up avec for some Mediterranean delights. Grab a drink And finally, let's end our list on the drinks menu. West Loop has lots of bars and pubs to drown some suds. Head to Lone Wolf or Haymarket Pub for your craft beer needs, with plenty of local Chicago brews on tap. For some exotic cocktails, give Kumiko a try, which provides a Japanese twist on the usual mixer affair. If you want a variety of spirits, stumble to CH Distillery. And that's our list of things to do in West Loop, Chicago! Enjoy!
Dom Bewley
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Famous Chicago Landmarks & the Most Instagrammable Places to Take Pictures in Chicago

All vacations are essentially about the experience – the sights, sounds, and tastes of the attractions you visit and the streets you walk. The way you felt at the top of the Ferris wheel, or the awe you experienced looking down from the top of a 96-story building. Beautiful memories, but all memories fade. You want the pictures you take to be the kind of shots you might frame, the ones you’ll treasure years later. To help you out on your quest to find the perfect photography subjects, we put together a list of the top places to take pictures in Chicago. Best Ways to See Famous Chicago Landmarks There’s plenty of great places to snap the perfect instagram photo of famous Chicago landmarks during your trip. Here are a few fun ways to help you get around while sightseeing... Hop On Hop Off Chicago Bus Tour Architecture River Cruise Bike Rental from Bike and Roll Chicago Here's some more info on fun Chicago sightseeing tours. Many of the photo opps we listed below are located near some of the top attractions in the Chicago – so you can combine the best sights with the best things to do. See all available passes, attractions & prices – Learn more. Best Places to Take Pictures in Chicago 3. The Picasso sculpture in Daley Plaza An icon of twentieth century art innovation, Picasso is known for his use of abstract shapes and re-interpretation of form. This untitled sculpture (usually just called the Chicago Picasso) was actually commissioned specifically by the architects of the Daley Center and has never been displayed anywhere else. For this reason alone, you need to snap a shot of this one-of-a-kind statue. Plus, how many museums let you take photos of Picasso’s work? Daley Plaza is on the Loop, near a number of popular Chicago attractions, so it’s a good central place to start your day. 9. Wrigley Field As the second-oldest baseball stadium in the country, Wrigley Field is a historical institution and a must see Chicago landmark. It has been home to the Chicago Cubs since 1916, and much of the exterior architecture reflects its heritage. Of course, a lot of the interior has been updated very recently to accommodate modern MLB standards, but plenty of historical elements remain -- including the old fashioned scoreboard on the side, proclaiming your presence in Wrigley Field. Even if you’re not a Cubs fan, it’s an iconic building in American professional sports. Let's Recap While this list is by no means exhaustive, it does contain a bunch of our favorite places to take pictures in Chicago. From the most popular attractions to skyline views and scenic parks, there’s something to suit every taste when it comes to Chicago photo opportunities. Remember, a number of these famous Chicago landmarks and attractions are available with the Go Chicago Card, where you can save on combined admission prices vs. paying at the gate.
Katie Sagal
Things to do in Old Town Chicago
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Things to do in Old Town Chicago

Ahoy there, sailor! Are you taking the old steamboat over to the growing Metropolis they call Chicago? I do declare, you may be delighted by the city's Old Town district. There's plenty to do and see there, partner. Want to know what? Well, we'll tell you right now. Here are some of the best things to do in Old Town, Chicago! Including: Stand up A little history The beach Immersive art The theater and more! Second City Let's kick things off with the best medicine. We're talking about laughter, of course! What if we told you that Old Town is where some of the best and brightest comics strutted their stuff before becoming famous? You might think that's nonsense. But believe us, it is not. Many of the comic greats you see on your screens today cut their teeth at Second City, America's premier improv club. Through the years, comedy legends such as Bill Murray, Alan Alda, John Belushi, and Mike Myers have called it home, and you'll always find hilarious hijinks going on there. So go check it out! Who knows, maybe you'll stumble upon the next big thing in comedy when you visit? If you like to laugh and you're visiting Chicago, Second City is easily one of the best things to do in Old Town! Chicago History Museum If you're visiting Chicago, you might not know much about the city or its history. Would you like to know more? Well, never fear, because the Chicago History Museum is here! Step inside, and discover the city's rich history from a number of exhibits. At the Crossroads of America exhibit, you'll get to relive the most significant events in the city's history, meet Chicago's most renowned leaders, and learn how culture shaped Chi-Town throughout the centuries. Step into Sensing Chicago, and appreciate the city with all five senses! Hop on a high-wheel bike, hear the roar of the Great Fire of Chicago, smell the unique scents of the Union Stock Yard, and catch a fly ball at Cominsky Park! Perfect for big and little kids alike. Enter the Abraham Lincoln exhibit and learn all about the life and struggles of one of the country's best presidents! See how his leadership shaped the Civil War, and the events that led up to his assassination. And finally, check out Facing Freedom in America, which charts the struggle of many people's efforts to achieve freedom in the country. These interactive displays will open your mind to the plights of many peoples, from suffrage to the civil rights movement. North Ave Beach Need to relax? Unwind? Lacking a little Vitamin D and want to get tanning? Then you'll want to hit the beach. Thankfully, Old Town has North Avenue Beach, which not only offers many opportunities for you to lounge or wade into the water, but also activities too! Head there in summer, and you'll find a slew of volleyball tournaments, bikes to rent, and opportunities to try out watersports like paddleboarding and kayaking. So, if you need a little sun, sea, and sand when you're in Chicago, go check it out! The Moody Church Whether you're religious or not, you may be partial to a grand spectacle. If the thought of grandiose architecture and awe-inspiring craftsmanship gets you giddy, go check out the Moody Church in Old Town. This grand place of worship was completed back in the 1920s, and stands as a testament to design. Go get your pray on, or simply attend to look around. You're sure to find someone on hand to talk you through the construction of the building, and the goings-on within over the years. Either way, it's a great stop on your travels through Chicago's Old Town! A Red Orchid Theatre Do you want to supplant your visit with dramatics? Go check out A Red Orchid Theatre. Widely considered to be one of the best theaters in the country, Red Orchid is comprised of multiple writers, actors, and directors, including Hollywood's Michael Shannon. Every year, their shows break new ground in the theater world, telling edgy, gut-wrenching stories that are performed with finesse. So, why not go check out one of their critically-acclaimed performances when you're in Old Town? Eat, of course! All that reading and planning your trip to Old Town has probably left you hungry. Let's fix that. Thankfully, Old Town has a whole host of delightful restaurants and cafes for you to visit! Want to start your morning just right? Try Kanela Breakfast Club, a Chicago eatery with spots all over the city. Omelets, eggs, grilled cheese, and much more await you on their diverse menu. If you want some delicious cocktails to wash down a hearty meal, head to Happy Camper. During the day, you'll pair authentic pizzas with a host of drinks. During the night, you'll get to enjoy one of the best bars in the city! Want to sample barbecue that delighted the late, great Frank Sinatra? Then stop by Twin Anchors, which has quality ribs on offer all year round. Are you feeling continental? Try La Fournette, a traditional French bakery right in the heart of Old Town. Alongside the usual suspects of baguettes, croissants, and sweet pastries, they also have salads, soups, and much more behind the counter. So, whatever you feel like eating, Old Town's got you covered! Get immersive with Van Gogh And finally, let's end this rowdy route through Old Town's best bits with something different. If you've dipped your toe into the world of art, you know about Vincent Van Gogh. The Dutch Post-Impressionist painter is one of the most critically-lauded artists in the world. His paintings sell for millions, and his best works hang in the most fabulous galleries on Earth. You might know of Van Gogh, but you've never seen his work like this. At the Immersive Van Gogh experience, you'll see his works come to life with animation. Walk through his most famous works, like Starry Night, Sunflowers, and The Potato Eaters. It's an illuminating experience, and with over 2 million visits to its original Paris installation, it's a easily one of the best things to do in Old Town when you visit Chicago! And that's our list of the best things to do in Old Town, Chicago! Enjoy your visit!
Dom Bewley

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