Cliktrips likes the beach, palm trees, mountain hikes, desertscapes, forest walks, the jungle, tropical islands, swimming pools, lake swims, rocky seaside cliffs, sunsets, soundbaths, hot tubs, the occasional cold plunge, bicycle rides, road trips, spritzes of all kinds, lots of snacks and the colors pink and green. Cliktrips also enjoys late night techno parties, balearic rooftop hangs, weird weekenders, tropical sounds, trippy disco, and dancing ‘til dawn.


Trippin' with Tom Windish of The Windish Agency

Trippin' with Tom Windish of The Windish Agency


Originally published July 2011

Welcome to our new series, “Trippin’” where we ask people simple travel-related questions and get back amazing answers. Tom Windish is the main man behind one of the biggest and best booking agencies in North America. 

The Windish Agency books loads of up and coming indie, electronic and rock bands as well as new and established DJs. Chances are if you’ve been to a show or a club in the last few years, you’ve seen a few his acts perform. And I’m pretty sure he books at least 75% of everyone at Coachella too.

Top 5 recommendations (eat, sleep, drink, clubs, things to do) in your city or a city you love

I’ve spent 15 years in Chicago but recently moved to LA for the Winters.  I’m no expert on LA yet so I’ll focus on the best that I think Chicago has to offer.

1. Big Star - This is an amazing taco restaurant with great drinks.  The best part is how awesome it is, and the worst part is how popular it is.  The dollar tacos are to die for.  The chef, Paul Kahan, is phenomenal and also cooks for Avec and Publican.  You can get out of this place with a full belly and a buzz for $10, but I’d recommend spending a little more on the higher end tequilas.

2. Avec - This IS my favorite and Paul Kahan also works the kitchen here.  The decor is amazing, all wood and the back wall is completely covered with the bottoms of wine bottles.  This is the first place I ever ate a bacon wrapped date and it’s still my favorite place to have them.

3. Danny’s - This is my favorite bar in Chicago.  I used to DJ here years ago and also booked Four Tet and Mr. Scruff to play here.  It fits 100 people and there’s never a cover charge.  When you want to be social and have a cheap drink, this is the place to go.  If you’re in Chicago for one night and want to go out, this is the place to try. They play great music, pour stiff drinks and most nights a small but vibrant dance floor will spontaneously appear.  Only bummer is the line to get in.  They used to pack the place but the city has gotten strict with capacities and you might have to wait.  Or show up around 9 and it should be fine.

4. Longman & Eagle - This is one of my favorite restaurants in Chicago.  Lots of funky meat, locally grown and sourced food.  There’s also a six room hotel above it.  Full disclosure, I’m an investor, but trust me, it’s a gem.

5. Lake Michigan - As in THE lake.  Go here if you go to Chicago.  Walk, run, bike, whatever, just go here.  They have fireworks downtown on the lake every Wednesday and Saturday in the Summer.

Honorable mentions: Hot Doug’s, Rainbo Club, Violet Hour

Favorite hotel anywhere in the world (under $300 USD/night)

I actually find Shoreditch House in London to be really useful and I stay here more than any other hotel in the world.  I like it because it’s not too pricey by London standards, it’s in the East side of London where I spend most of my time, and it’s connected to the Shoreditch House club where I hold most of my meetings while I’m in London.  Plus there’s a gym and the most diverse collection of bath products I’ve ever seen at any hotel ever.  The rooms aren’t massive by any standards, I usually stay in the “small room” but I truly appreciate being able to run back to my room for a quick nap between meetings so I can combat my all too present jet lag.

Favorite vacation (beach, mountain, non-city) destination

Unfortunately I don’t take many vacations.  Last year I went to Cape Town, South Africa and stayed with my uncle for almost two weeks.  To date, Cape Town or really, 1 hour outside of Cape Town is the most beautiful place I’ve ever been.  Ocean ocean ocean.  That’s all you see for miles and miles and miles.  There aren’t many people around and the landscape is insanely beautiful.  If you like wine (I don’t really know how you couldn’t like wine in South Africa), you will love it here.  There are hundreds of wineries here and they are much less expensive and much nicer than the ones I’ve been to in Napa Valley.

The Harmony Hotel. Nosara, Costa Rica.

The Harmony Hotel. Nosara, Costa Rica.

The Boggsville Boatel. Far Rockaway,NY

The Boggsville Boatel. Far Rockaway,NY