Things to do in Old Town Chicago

Published: July 18, 2024
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!
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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.

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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!

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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!

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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
Go City Travel Expert

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Top things to do in Chicago for birthdays

A birthday is a great excuse to push the boat out and treat yourself to something beyond the everyday. When it comes to things to do in Chicago for birthdays you’re not limited to a night out in a speakeasy-style bar or a smart restaurant – although both are excellent options for sharing the special day with friends and family. In fact, the windy city is a breeze when it comes to finding unique ways to mark a birthday. Don’t believe us? Just take a look at our pick of the crop! Spend your birthday on the beach Because of the city’s location on the western shores of Lake Michigan, summer babies can spend the day on the sands of any of Chicago’s beaches. For atmosphere, head to North Avenue Beach, one of the most popular. Decked out with volleyball courts, jet ski and other water sports rentals and even WiFi, there’s something for everyone. A short walk from the Museum of Science and Industry, 57th Street Beach is generally a little more laid back, although still provides the chance to try your hand at stand-up paddleboarding or canoeing from its northern end once you’ve soaked up enough of the sun from the yellow-orange sand. For the ultimate in tranquility, consider heading to Promontory Point in Burnham Park instead, where the sand is replaced with stepped limestone blocks and plenty of opportunity for a picnic. But don’t do away with your swimwear if you celebrate your birthday during the winter months. Simply switch the beach for one of the city’s top spas. Lounge by a temperature-controlled indoor pool whilst cocktails I brought to you, feel rejuvenated with a full body massage, or soak in a wine bath – the antioxidants are said to be kind to the skin. Celebrate with a glass in hand If bathing in the stuff seems like a waste, you’re in luck – the nearest vineyards are just a few miles out of the city. Stripped free of snobbery, the Valentino Vineyards manage to cram 20 different varieties of grape into their 20 acres roughly 30 minutes’ drive from downtown. Their tasting room becomes a hive of activity during the summer months, hosting tastings of their award-winning vintages, tours of the vineyard and seminars for anyone keen to learn a little more. Sticking firmly downtown, on clear evenings the city’s rooftop bars are other ways to celebrate your birthday in Chicago. Perched on top of the buildings of Navy Pier beside Centennial Wheel, Offshore Rooftop & Bar has entered the record books as the largest rooftop bar in the world. Thanks to a retractable roof, its third-story views of Lake Michigan can be enjoyed for birthdays at any time of year. If you’re after a space that’s a little more intimate, head to upmarket Homestead on the Roof in West Town whose food menu is as good as its cocktail list. Alternatively, take the elevator as far as it will go in your hotel – it’s more than likely any downtown stay has its own rooftop perch. Party with a view The Chicago skyline is difficult to tire of and fun things to do for a birthday in Chicago include taking in the city from its tallest buildings. Once the tallest building on Earth, and still one of its loftiest, the Willis Tower contains Chicago’s highest vantage point without recourse to a parachute or helicopter – the Skydeck. Over 1300 feet up on the 103rd floor, sunset is the prime time to visit. To make things extra special, the 99th floor contains a second space with the same panoramic views of the city that can be hired out for private events. The Skydeck isn’t the only fun thing to do for a birthday in Chicago where you’ll find personalized treatment. Head back to Navy Pier and you can step aboard the Centennial Wheel’s VIP gondola. Its plush interior has enough seating for four, ideal for smaller gatherings. If our previous mention of helicopters piqued your interest, you’ve got various options for taking to the air. Most operators hover around the skyscrapers of downtown before skirting the lakeshore on a flight that will leave you enthralled, mildly terrified or a bit of both. Dine in style Back on the ground, Chicago has plenty of places to treat the taste buds. Going all out, there’s somewhere in the region of 20 Michelin-star restaurants adorning the Near North and Near West Side neighborhoods alongside Lincoln Square, South Loop and Chinatown. Top billing goes to two star Moody Tongue, pairing a seasonal tasting menu with their very own beers, whilst Spiaggia has brought the culinary world’s top award to Italian cuisine for more than a decade. In addition to cuisine which passes muster for the Michelin team, Chinatown has spots turning out incredible flavors without breaking the bank, whether it’s the chili heat of Szechwan, crunch of deep-fried dim sum or freshly-baked barbecue pork buns that take your fancy. Elsewhere in the city, those looking for a relaxed approach to dining might want to combine it with a couple of hours of fun at a bowling alley – both family-friendly and weatherproof options for things to do on your birthday in Chicago. Go City does the hard work so you have a birthday to remember Birthdays don’t come cheap, unless of course you’re in Chicago with Go City. We give visitors to the world’s top cities huge savings on admission to top attractions, including many of the things to do in Chicago for birthdays we’ve mentioned in this post. Not only is taking advantage of this reduced attraction admission incredibly easy, but you’ll generally get to skip the ticket line and keep much of the flexibility that’s important when on vacation. Not sure where to start? Follow @GoCity on Facebook and Instagram for what’s hot and what’s not right around the globe!
Ian Packham
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Where to stay in Chicago

Made up of a long list of neighborhoods and districts each offering something different, deciding where to stay in Chicago can be a bit of a headache, especially if you’re a first-time visitor to the city. Whatever you’re looking for out of a leisure trip to the windy city, our pick of the best areas of Chicago to stay is sure to be a help! The Loop Enclosed by the Chicago River to one side and Grant Park to the other, the Loop is probably the best place to stay in Chicago for those new to the city since its streets include the central business district and many of the city’s top attractions, including the Willis Tower’s Skydeck observation level and the Art Institute of Chicago. It takes its name from the elevated railway which has looped around it since the Great Fire of 1871. Synonymous to most with the downtown area, it’s also one of the commercial hubs of the city. Being at the heart of the action (Route 66 starts here too), there’s no shortage of hotels either. Predominantly populated by luxury stays – the Hyatts and Radisson Blus of this world – budget travelers will likely find themselves looking at more affordable neighborhoods nearby, such as Lincoln Park. However, the Loop does it have a good quantity of backpacker hostels for those just looking for a central place to lay their head at the end of a long day of sightseeing. Streeterville Immediately north of the Loop on the shores of Lake Michigan, the Streeterville neighborhood is still close enough to downtown to be a worthwhile base and is a good pick for solo travelers and visiting couples. Known to be a very safe neighborhood in Chicago for visitors, it has some similarities to its southern counterpart. Gleaming tower blocks line the Magnificent Mile (a part of North Michigan Avenue), containing roughly 450 stores as well as the famed 875 North Michigan Avenue (John Hancock Center). Its southern extent stretches out into Lake Michigan thanks to the 50 acre Navy Pier. Its rides include Centennial Wheel, which replicates the world’s first Ferris Wheel, built in 1893 for the World’s Fair. Lincoln Park A little further out, but linked to the rest of the city by a number of metro stations and lines, Lincoln Park is one of the largest and most affluent districts in Chicago’s North Side. It is popular with young families and urban professionals, ensuring it feels fresh and ever changing. Named after the city’s largest park, which sits beside Lake Michigan for an uninterrupted seven mile run, the area is one of the best parts of Chicago for those on a budget. Attractions include the 32,000 creatures which call Lincoln Park Zoo their home, as well as Chicago History Museum, the first port of call for anyone interested in discovering how Chicago became one of the world’s leading cities. Lincoln Park also contains the northern half of Old Town, where buildings remain low to the ground – at least by Chicago standards – to create a homely feel. This is where you’ll find the Second City Theater, the previous stomping ground of everyone from Tina Fey to John Belushi. River North It may not have the lake shore, but River North does have a reputation as the coolest place to stay in Chicago. Separated from Streeterville by the Magnificent Mile, River North oozes stylishness and perhaps contradiction too – it has more galleries than anywhere outside of Manhattan, but is also known for its nightlife. For this, you should head to Hubbard Street. The banks of the Chicago River have to be the top place for a stroll in the area, whilst landmark buildings to look out for include the Wrigley Building and the monumental behemoth of a structure known as Merchandise Mart, whose exterior façade becomes the world’s largest projector screen for a few months of each year. A good range of restaurants, many with riverside terraces, means you’re unlikely to go hungry for long. West Loop That said, foodies should stake their claim to accommodation in West Loop, which – that’s right – is west of the Loop. Occasionally also known as the Near West Side, West Loop shines from a gastronomic perspective, with Greektown and Little Italy just two destinations you should be aware of thanks to the twentieth century’s influx of immigrants into this former industrial port area. Randolph Street is otherwise known as Restaurant Row for good reason, but for sumptuous food without any pretension head to the French Market tucked inside Ogilvie train station. Its 30+ independent vendors make it one of the best spots in the city for fresh ingredients as well as mouthwatering dishes from sushi to empanadas. Seating is available. Wicker Park Well-to-do Wicker Park is growing in confidence when it comes to where to stay in Chicago. Northwest of West Loop and centered around the Damen metro stop, this neighborhood has the sort of self-assurance which usually leads to great things. And Wicker Park is no exception to this rule. A charmingly informal blend of eclectically-stocked clothing stores, groundbreaking restaurants and we-just-have-to-stop-there bakeries, Wicker Park is also pretty hot when it comes to night spots, with a wealth of live music venues all vying to be the place to head. With median house prices of $550,000 it can never really be called hipster, but that’s certainly the vibe it gives off. Budgeting for trips to Chicago Finding where to stay in Chicago that’s right for you comes down to a balance of location, feel and price. The best neighborhoods in Chicago for visitors are generally those in and around the downtown area, although the closer you are to the Loop, the higher the per night cost you’re probably looking at. When it comes to attraction admission, you can make incredible savings simply by opting to travel with Go City. Our pre-pay passes take all the mystery out of budgeting for trips to Chicago whilst providing you with great savings on many of the city’s top attractions.
Ian Packham

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