Escape Lollapalooza: What To Do In Downtown Chicago

Lollapalooza 2015 weekend is upon us, and the weather forecast is in. It’s as expected, with predictions for high heat and high humidity. Add that to the expected 100k-a-day crowd at the sold out Chicago event, and there’s a good chance, if you’re attending, that you’re going to need a break. Sans tickets? No worries. Hang by the outskirts, listen from afar to some bands, and take yourself on this Escape Lollapalooza tour.

Featured here are the best (and some of the most underrated) spots to grab a beer, a photo, or simply some solace from the weather, right near Lollapalooza grounds, located in downtown just west of the waterfront. 

(The Original) Billy Goat Tavern

430 North Michigan Avenue

“Cheezeborger, cheezeborger, cheezeborger!” One day, a long time ago, John Belushi, Dan Aykroyd, Bill Murray and Loraine Newman starred in an SNL skit. It was pretty darn good. It was based on an actual restaurant, and that venue is none other than the Billy Goat Tavern

While the burger joint now boasts an impressive 9 locations in the greater Chicagoland area, it all started underneath Michigan Avenue. You read correctly. The restaurant is located on the lower level of Michigan. Chances are if you’re in from out of town you may not even realize there’s a whole network of streets where the sun doesn’t shine in Chicago. Remember all those great chase scenes from The Dark Knight? Those took place right down the street from Billy Goat on Lower Wacker.

What should you order when visiting this local staple? Well, if it isn’t already abundantly clear, a cheeseburger. But fret not, they also have a really good egg & cheese sandwich, and for robust meat lovers, a very intense Roast Beef sandwich. Add to that cheap draft beer, and one of the best condiment stations I’ve ever seen (pickles anyone?).

Navy Pier

600 East Grand Avenue

Alright, so it’s definitely not a secret, but it’s still pretty darn cool. Navy Pier, originally constructed in 1916, is absolutely a tourist favorite, but it really does have something for everyone. The small strip of land that jets out into Lake Michigan is filled with shops & restaurants, and also home to plenty of Chicago skyline tours and an amazing view of Chicago.

But why should you go there now? The grand ol’ ferris wheel was originally planted on Navy Pier for the 1893 World’s Fair served as inspiration for what is currently located on the grounds. But it won’t be for much longer. The ride has been running since 1995, but even good things must go. Or be improved. Just recently announced in the Windy City are plans to replace the Ferris Wheel with a bigger, newer version – think the London Eye or that new fancy version in Vegas. If you’re one for nostalgia, a warm breeze and a little fear (you aren’t totally enclosed, folks) take the ride before it comes down in September.


412 N. State Street

Rossi’s is so cool they don’t have a website. But really. Or the hosting is down. You never know, but in all fairness they don’t need one. I’ll tell you everything you need to know:

  • Cash only.
  • Hamm’s Tall Boys.
  • Jukebox.
  • Phil Collins, “Billy Don’t Lose My Number” – on said jukebox.

Ok here’s the reality, it’s one of those new, modern jukeboxes so of course it has “Billy Don’t Lose My Number”, but the key piece about Rossi’s is that at this bar there’s a realistic shot that you’ll actually hear the song you picked to play that very night. Madness!

The local haunt is well liked, but is more of a stopping place than an all-nighter. It’s located just around the corner from the very clubby Hubbard Street bars, but you’re more likely to find a unique mix of business people, conference goers or tourists and smart folks from the River North and Streeterville neighborhoods who just know a good bar when they see one.

The Pedway

Everywhere and Nowhere

The Pedway is a very unique Chicago anomaly that connects a large series of transportation channels, buildings, shops & restaurants all well below the city. It links more than 40 blocks of downtown Chicago. But how do you get to it and how do you master it? I’m still work-in-progress on the latter, but you find the Pedway via numerous different methods. CTA stations downtown connect to the Pedway. The Block Thirty Seven Mall connects to the Pedway. Marshall Field’s, er Macy’s, connects to the Pedway. But instead of me giving you lackluster directions to a place you’re probably questioning even really exists, follow this handy guide.

Why do you need the Pedway this weekend? Few reasons. For one, this summer has been one of the rainiest summers Chicago has ever seen. While umbrella weather isn’t forecast, in this city you have to be prepared for everything. In the event things turn ugly, the Pedway is a great escape to commute across the city without being exposed to the elements. Even if it doesn’t rain, it’s going to be hot & humid. Enjoy some shade in a nice air-conditioned restaurant all while feeling worlds away from the madness of Lollapalooza 2015. 

South Loop Club

1 E Balbo Avenue

Adjacent to but now on the southeast side of Lollapalooza, is the South Loop Club. This spot can serve as, among other things, a great meeting place if you want to establish an off-site location to connect with friends. Why? Since this bar & restaurant is south of both Jackson & Congress, it means you won’t be in the muck of train commuters headed downtown, or extensive street traffic. They serve a huge menu ($20 for a hot dog and beer inside fest grounds? No way – you have a wristband.. bounce out and get some real food), and of course a full bar. My recommendation: head here first. Nothing like a spicy bloody mary to kick off a fun filled day that will be followed by constant $8 Bud Lights in 90 degree sun. Maybe drink a few glasses of water while you’re there too.

The Bean Cloud Gate



The Bean is located inside of Millenium Park, just off of Michigan Avenue, north of the central Lollapalooza main entrances. The Bean doesn’t really have an address. The Bean doesn’t need an address. Honey badger don’t care.

Someone who does care is artist Anish Kapoor, whom was actually pretty displeased with the fact that Chicago named his work for him, and chose “The Bean”. Why? Well it’s obvious, it looks like a bean. But Anish Kapoor favored “Cloud Gate”. Does anyone in Chicago refer to this majestic piece of work as “Cloud Gate”? Probably the 6 people who refer to the Sears Tower as Willis. 

Revealed to us literal Chicagoans who call things like they see them, The Bean became part of our lives in 2004 and not everyone was so happy with it. The project, along with the grander Millenium Park, came in way over budget, costing tax payers millions, and was way late on delivery. But time has passed, all has been forgiven, and now the giant mirror that predates the selfie-explosion is very near and dear to our hearts.

 Lollapalooza is a very unique music festival in one of the biggest cities in the nation. It doesn’t take place in a stadium or parking lot, but one of the most recognizable (and expensive) parks in the country. Take advantage of the proximity the event has to countless local favorites by escaping Lollapalooza. Your festival going experience will surely be better because you did. If not for any other reason, just remember, #portapotties.