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!


  • Christina Edwards

    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!

  • Alex Antonopoulos

    Any plans on expanding to other cities on the horizon?

    • SimonVimbly

      Yes! Boston and DC are up next!

  • Cassie

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

  • mike

    i just booked a brewery tour for sat

  • Kathy D

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

  • Diane Wall

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

  • The Mayor of Medinah

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

  • wraythe01

    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

      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!

      • Bill Hicks


    • Mimihaha

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

    • Anon Ymous

      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.

      • Bill Hicks

        You are correct. Wraythe is incorrect.

  • LeotheOrangeCat

    Whoa . . . watersports?

  • John Doester

    Link on CNN “7 Breathtaking Places Most Chicago Natives Don’t Even Know About”. Anyone know where I can find this article, because this sure isn’t it.

    • jeansandjacketrequired

      This article is just click-bait… just a bunch of links to things all Chicagoans know about. Disappointing article.

  • NM156

    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

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



  • Chicagoan

    It’s called pizza not pizza pie. Apparently this company doesn’t know Chicago very well or else they wouldn’t have made that mistake.

  • Jack

    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

      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

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

    • Malta

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

    • Bob Skilnik

      Cry baby!

  • Reece Why

    Don’t know about? 1 site I will never click “vimbly.”

  • Better

    Will never, ever use Vimbly BECAUSE of how you lured me here. Dicks.

  •ü/100006483932228 Ar U. Gaetu

    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.

    • Larry

      Sounds like your just extremely cheap.

    • Amie

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

      • MM71

        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!

    • MM71

      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.

    • Jules

      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.