Finding Awesome Things To Do In Chicago Just Got Way Easier

Chicago. One of the most dynamic and diverse cities in the world. And despite a certain nickname, second to none. You know it, we know it, and that’s why we are so happy to announce that Chicago is the first city that Vimbly is expanding to!

From a pizza pie beyond compare, to some of the most beautiful and breathtaking city architecture that we’ve ever seen, Chicago has it all. But are you really experiencing your city’s full, glorious potential?

We can get you there. We can connect you. Vimbly can make life more interesting.

If you need a last minute date idea – we’ve got neighborhood food tours, cooking classes and wine tastings.

If you want to find activities to occupy out of town friends and family – see some sights with Lake Michigan speed boat rides, historic walking tours and Chicago architecture river cruises.

If you’re busy at work and need a quick plan for an epic evening out – we have local brewery tours, bar crawls and mixology classes.

If you want a memorable way to entertain clients – book a helicopter tour, golf or a brunch cruise.

If you want to get in shape or stay in shape – there are a ton of dance classes, martial arts classes and water sports available.

If you’re just trying to decide what to do with some buddies – we’ve got skydiving, burlesque shows and photography adventures.

And if you simply want to try something new…

Vimbly gives you access to thousands of awesome local activities that are nearby, affordable and free to book  with one simple, easy process!

We at Vimbly are truly honored to have the opportunity to serve The Windy City. You are the most important thing to us, so we’ll always be here for you to answer any questions or concerns that you might have (or if you just want to say hi!). Don’t hesitate to reach out at any time.

We think this could be the start of something beautiful.


Happy exploring from Team Vimbly!


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42 Responses to “Finding Awesome Things To Do In Chicago Just Got Way Easier

  • Z Old Guy
    1 year ago

    As an old guy who’s lived here 6 decades, I’m willing to see what your NYC team turns up. Looking forward to some new ideas.

    Just 1 suggestion — appreciate your opening comment about the pizza — and maybe “pizza pie” is acceptable where the slices are folded — but no native Chicagoan would ever use those 2 words together. Either one or the other works just fine.

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  • Downstater in City
    1 year ago

    I grew up in a farm down about 2 hours south of Chicago (“Downstate”). Since I left home at 17 I have lived in San Diego (in the Marines), Washington, D.C., New York, Tampa, Hong Kong, and Sao Paulo, Brazil.

    I had great experiences in all of those cities. But for me, hands down Chicago is the best place I have ever lived (been here for 12 years).

    There are challenges, without a doubt. It can be pricey. In the loop you go for a show and it costs $40-50 to park your car. If I had a dollar for every person that complained to me about parking I would be a rich man. BTW, Chicagoans think its expensive also.

    You can also drop $200 in an evening pretty quickly between dinner, drinks, cabs and whatnot.

    The weather in winter is awful. THis last winter was the worst one yet. And we really don’t have a spring. One day its cold, and the next its just hot.

    All of these drawbacks are real, and I have found that big cities are not for everyone. Most of my family, in fact, has stayed downstate.

    But if you are looking for the best all around quality of life, Chicago beats anywhere else I have ever lived.

    Why do I say that? Let me give you some specifics.

    First, it has the best mix of affordability and quality of life of any big city. New York is the capital of the world. No place like it. And Chicago is not NYC. It is an American city in the heartland. Consequently you can only get about 80% of what you can get in NYC. But the cost of living is much lower than NYC, and for me that is worth the trade.

    As an example, I own a condo in Lincoln Park, which is a nice Chicago neighborhood. I am close to the lake and its parks, I have great bars and restaurants that I can walk to in five minutes. The streets are safe and clean. And I can be downtown on the bus to work in 25 minutes. My condo cost me $290,000. Now admittedly I bought it at the trough of the downturn so I got a great deal. And its a vintage building (my unit however was completely gutted by the prior residents). I have to walk up three flights of stairs, and I park on the street. This unit in NYC or San Francisco, however, would easily sell for 5 times what I paid for it. And I have friends that live in the Marina or in Tribeca. I have to say I like my neighborhood better.

    Renting here is also cheaper. Now it is still not cheap. If you want to rent a 2 br in my neighborhood you are looking at $2000 a month minimum and it goes up from there. But a NYC or SF equivalent is at least double.

    My salary in Chicago is about 80% of what I made in NYC, but my money goes a lot farther here.

    One of the best things about Chicago is the summer. There is simply no better summer anywhere on the planet.

    Why do I say that? Because (i) the weather is perfect. Hot but not scorching. Very little humidity. And a nice breeze off the lake. Second, the lakefront is simply spectacular. The entire city comes out along the lake during the summer and it is glorious.

    Now some would say the summer is so intense because people are stir crazy after the long winter. And there is a lot of truth to that. The funny thing, though, is that I always forget the bad winter and remember fondly the great summers.

    This is in contrast to NYC (too hot and smelly in summer-although fall and winter in NYC are great)., or SF (never really warms up). And if I have to make trade-offs, Chicago works best.

    To me, the big trade off in Chicago is the lack of other areas to visit. Many people go to Michigan or Wisconsin to lake homes. But this cannot compare to being in NYC and hopping the train to Boston or DC. Or being in SF and driving out to Napa or down to Carmel.

    But all else being equal, I love it here. So don’t be afraid. Chicago is a warm, welcoming city. Try it and you just might fall in love.

    • Mackdaddy
      1 year ago

      Could not agree with you more.
      I have lived in the NYC area and your assessment is spot on.
      Also, among the Big 3 cities in America, Chicago is indeed the most livable if you can get through the winter.

  • Displace Country Girl
    1 year ago

    Clearly, you people don’t know anything about America or being American. Chicago is MIDWESTERN. It’s not East Coast. It’s not West Coast. It’s not “the South.” Nor is it New England. Folks, Chicago is Midwestern, and if you don’t understand that – it’s not for you to understand.

    And all the “bad” stuff about Chicago? Yep. . .it’s in ALL the major metropolitan areas of the U.S., and to some degree in all the “major metropolitan areas” on the planet.

    Me? I’m from “the country.” I remain amused at the people from the suburbs who like issue DISCLAIMERS that they’re not “from” the City – when it’s ALL the “metropolitan area.”

    And of course, there’s a solution if this isn’t the place where a person wants to be. . .U-Haul or Atlas — either one will get you where ever it is on the continent that you’d rather be. Among the “big” cities in the U.S., Chicago is eminently livable.

    For the record, I’ve been here since the early ’90s. Completed graduate school, and lived an “OK” life. . .and I STILL say, every chance I get, that “I’m not from here.” BUT! I am from THE COUNTRY…and that’s a long, long way from either urban or suburban. For the record, I love it. It IS a world class city. Also for the record, there are places in this city that NO ONE goes – except the people that live there. That’s just the nature of the beast… Finally? One day, I AM going back “home” – but I haven’t yet put that date on my calendar. One reason for that is SUMMER…

    Nothin’ on earth that’ll get me hummin’
    Like a heat wave comin’, I’ll come runnin’
    With her makin’ that tan in the broad daylight
    And every night is a Saturday night

    And everything’s right with the summer comin’
    I’m the first one standin’ in line

    If you know those lines, you’re “not from here” either, eh?

    • Displaced Country Girl-Again
      1 year ago

      OMG. I’m so sorry for the errors/typos in my post. There’s no edit to clean it up after it’s “published.” ugh. I didn’t realize that I wouldn’t be able to “fix” it! YIKES! . .poor site design.
      Displace*D Country Girl

  • Vimbly “hearts” the logo for the band Chicago, eh? Pretty weak.

  • I live just 30 miles outside Chicago, within 2 blocks of a major Metra station, and I haven’t been in Chicago in over 20 years. Far too expensive to do anything. The CTA is confusingly unusable for anyone outside of the city, and parking is very expensive, too. Add to that, the cost of theatre tickets, food and a few drinks, and the whole night with someone special approaches a month’s rent. Even if you stay in the “safe” areas, you risk being robbed (a friend lost his father’s watch that way). The safest way is to spend $200 for the necessary taxis to take you to where you need to go (you must tell every cabbie you know the shortest route because “you live in the area”, otherwise he’ll take twice as long to get anywhere, claiming he doesn’t know English. Has never failed every time I go to Chicago.)

    The best places aren’t in Chicago, they’re in the burbs. For a night out, try the Woodstock Opera House for a celebrity performer, then walk over to get a bite to eat at a local restaurant then onto a cozy pub. By the way, the Metra rail station is just 2 blocks from the brick streets of the main town square where everything is located. (Nearly everyone has seen the town, it was featured on “Groundhog Day”.) It’s about as safe and quaint as it gets. The best part; parking is always free, people are very friendly, gas is cheap, and it doesn’t smell like urine and old dumpsters.

    • Sounds like your just extremely cheap.

    • Yes, a night out in Chicago could approach a months rent in cost…if you live in Woodstock. It’s a matter of perspective.

      • Yes. There is a movement of money from the burbs to the city which has made everything more expensive (supply and demand). Chicago is a world-class international city. I’m sure you can go to Kentucky and live for a lot less, but then you would be in Kentucky!

        • Site Lurker
          1 year ago


          Unless you’re in Louisville during Derby season. . .I’ve been to the Louisville Slugger factory/museum. Besides Churchill Downs and that museum – NOT a place to spend a lot of time. . .unless you are “from” there!

    • There is a reason things are cheap in Woodstock. Nobody want to be there! Chicago is pretty awesome if you have the money to enjoy it. It’s not a city for everyone, just like NYC is not affordable for many people. You have to pay to play here or else go to the burbs and enjoy Olive Garden and whatever chain restaurants you have out there. World class food and entertainment is not cheap.

    • Woodstock blowz, No culture, no real nightlife, and the food sucks. If I wanted to go to Mayberry, I’d go to Mayberry, where the people are probably genuine and friendly, unlike most of Chicago’s cookie-cutter suburbs. And yes, this article is misleading and sucks.

  • There is absolutely NOTHING in Chicago worth standing in line for, signing up on a waiting list, or making reservations…unless of course, it’s a for a flight out of this sh*thole.

    I was transferred here on a job assignment and CANNOT WAIT for this project to end….just a few more months….

    Seriously, when I moved everyone told me Chicago was great, the people were friendly…all nonsense!

    Majority of people here complain about EVERYTHING, negative attitudes, and obvious despair from second city dejection.

    SAYO-f*ckin-NARA can’t come soon enough!

    • Dr. J Ballz
      2 years ago

      Wah! Wah! Speaking of complaining…. I’ll just make the assumption that’s a trait of your home city. Don’t let the door hit you in the ass on the way out:)

      • Bill Hicks
        2 years ago

        It’s not. Most of us love it here. Hopefully this doofus has left by now.

    • Jack, if you feel this way about Chicago, I’d like to know what your hometown is.

    • Bob Skilnik
      2 years ago

      Cry baby!

    • NotFromHere
      1 year ago


      Of course, not every one is a good “fit” for the American Midwest.

  • Warning: that Chicago “diversity” is something you’ll want to avoid at all costs. Someday, the city will have scheduled tours of gang shoot outs for tourists, but until then, stick to the most un-diverse areas.

    • Mike Duffy
      2 years ago

      There are places even I won’t go, like the South Side and West Side. Too many gang bangers.

      • Mackdaddy
        1 year ago

        So I guess you would not dare go the University of Chicago, Hyde Park, or the Midway Plaisance, all of which have stunning architecture and relatively low crime. Ignorant.

      2 years ago


    • just think
      1 year ago

      Spoken like u voted for Bush Jr. twice…lol

    • Mackdaddy
      1 year ago

      You obviously don’t know what the diversity means. It does not mean non-white people. It refers to a mixture of people from different backgrounds–regardless of race. The high crime areas of Chicago actually have very little diversity as perpetrators and victims of crime are typically of the same ethnicity.

  • LeotheOrangeCat
    2 years ago

    Whoa . . . watersports?

  • wraythe01
    2 years ago

    The term, “Second City” is NOT a reference to Chicago’s standing relative to anyone else. It refers to Chicago after The Great Chicago Fire vs. Chicago before The Great Chicago FIRE. As many know, in 1871 Chicago burned almost entirely to the ground and many thought the city would have to be abandoned. The Great Chicago Fire destroyed over 18,000 buildings. One hundred thousand Chicagoans
    lost their homes, an uncounted number their places of work in one of the largest disasters in history. Then, in an amazingly short period of time the “Second City” of Chicago was built as a modern metropolis going on to host, just 22 years later, the World’s Columbian Expositon (The World’s Fair) in 1893 to celebrate the 400th anniversary of Columbus’ arrival in the New World in 1492. Second City is a term Chicagoans should proudly embrace as it speaks to the indomitable force of will that has shaped modern Chicago into what it is today.

    • Kalmbach
      2 years ago

      I always thought that it referred to being second in size after New York (LA didn’t count back then, or course). Still such a great place to be. The city burns down? We’ll just build a better one!

    • Mimihaha
      2 years ago

      The Second City was the title of a New Yorker article in the 1950s.

    • Anon Ymous
      2 years ago

      This is only, at best, somewhat true. It’s possible that Chicago had referred to itself as The Second City after the Chicago Fire. But by the late 1880s, the term was put into play SPECIFICALLY because of population increase and BECAUSE of the large size (passing Philadelphia) to campaign to get the World’s Columbian Exposition. Then, by the time the phrase gained national prominence (New Yorker article 1950s), it was SOLELY due to the large population.

      So, the original etymology, coming from the Great Chicago Fire or not, is up for debate, and I’ve yet to see anything besides Wiki links and anonymous web submission answers saying that it is. It could be true, or it could be someone in the last few years started definitively saying it was true when it’s not.

      But it terms of it gaining ground in the lexicon of both Chicagoans and around the world, The Second City became that way solely due to population, and not due to the Chicago Fire. There’s way too many authoritative references detailing this to not regard this as the reason the moniker stuck and has continued to be used. Unlike “The Windy City”, which has been corrected for years when people take it literally rather than politically figuratively and has never had an accepted secondary use, “The Second City” has only had one use for well over a century.

    • Srsly?
      1 year ago

      This is the most ridiculous nonsense I’ve ever heard. The term Second City has nothing to do with the Chicago Fire. Where are you getting your information?

  • The Mayor of Medinah
    2 years ago

    you should check out lower Wacker drive and all of the lower drives to see the real chicago

  • Diane Wall
    2 years ago

    I had no idea that we had so many cool food tours. I might have to do one on my birthday next month!

  • Kathy D
    2 years ago

    I’m surprised no one thought of this before. It makes so much sense.

  • i just booked a brewery tour for sat

  • Amazing!! I’ve been trying to find a good cooking class to take! This is perfect.

  • Alex Antonopoulos
    2 years ago

    Any plans on expanding to other cities on the horizon?

  • Christina Edwards
    2 years ago

    I’m so excited that you’re in Chicago now! I visit for work about 4 times a year and I can’t wait to book something!

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