banner image courtesy of Free-Photos from Pixabay

2019 is going to mark 28 years since Perry Farrell first conceived of the event known as Lollapalooza. I’ll take this opportunity to give you a firsthand walkthrough of a local’s perspective on what to do walking near Lollapalooza.

It’s almost August! Which means – it’s time for Lollapalooza!

8 stages. More than 170 bands from all over the world. A whole lot of merch and memories to take away with you...

Now, here’s the question.

Lollapalooza’s big. Why don’t you go bigger?

Why not take this opportunity to really get a feel of the Windy City?

Let’s start off with places to stay at, shall we?

Places to Stay near Lollapalooza

The Hilton Chicago

Lollapalooza takes place at Grant Park. Do you know what’s less than 5 minutes away?

The Hilton Chicago.

Rated 4.3 stars on Google and 4.0 on TripAdvisor, the Hilton is a sure bet for a visitor. And it’s only a few minutes from Buddy Guy’s Legends, an institution in the blues scene.

The Congress Plaza Hotel

Did enjoy John Cusack trying to escape the haunted hotel room in 1408?

Would you like to get a feel of a hotel where both Teddy and Franklin put up?

Then you need to check out the Congress Plaza.

This 520 South Michigan Avenue hotel was been named the most haunted building in Illinois. It also describes itself as the ‘Home of the Presidents’ due to a number of Presidents having put up there, including both the Roosevelts.

The Chicago Athletic Association Hotel

If you want to enjoy your Chicago sojourn with a stay at a 4 star hotel with a 9.2 rating on Skyscanner, complimentary rooftop yoga sessions, and variety of places to ‘dine and libate’, check out the Chicago Athletic Association Hotel.

You need to hurry up, though, if you want to do the yoga because the classes last till end July.

With where to stay selected, let’s now check out what to do

First, for some exposure to Chicago’s eclectic music scene.

Alternative Music near Lollapalooza

Buddy Guy’s Legends

Located on Wabash Avenue, this is more or less an institution in the blues scene in Chicago.

Whether your appetite is musical or gastronomical, Buddy Guy’s Legends can fulfil it.

With artistes like Jimmy Johnson, Guy King and Luca Kiella set to perform in August, Buddy Guy’s is sure holding its own against Lollapalooza.

And you could have on your plate their award-winning gumbo, jambalaya, chicken and ribs, and catfish po'boys and be clutching a glass of Buddy Brew.

Jazz Showcase

Two things happened in 1947. A military balloon (or an alien spacecraft; take your pick) crashed near Roswell in New Mexico. And NEA Jazz Master Joe Segal opened up a jazz venue in Chicago called Jazz Showcase.

Pat Mallinger’s gonna hold fort there during Lollapalooza, shortly followed by Jarrard Harris; and I don’t think I need say any more on it.

Located at 806 S Plymouth Ct., it’s a short walk away from Buddy Guy’s Legends. Ditto, from Grant Park.

Blues and Jazz don’t quite whet your appetite? Ancient history, the natural world and art are more your stuff?

In that case, Chicago may not be the place for you to visit....if you only have one or two days in hand.

Things to do near Lollapalooza

One of the largest museums of natural history in the world – the Field Museum – is located right here in Chicago. If you do drop in, make sure you say ‘Hi’ to Sue the Tyrannosaurus Rex.

On the other hand, if you want to learn how a Pollock differs from a Picasso, the Art Institute is the place you want to be at.

Fox in a Box Chicago

In the mood for some excitement? Want to visit the #1 Escape Room in the United States?

Hop on to the subway at Monroe and get off at Harrison, which puts you on S State Street within walking distance of W Polk Street.

Alternatively, you can walk down Michigan Avenue to the Michigan/Jackson bus station and catch a bus to take you to the Michigan & 8^th Street stop, which puts you on E 8^th Street and then it’s barely a 10 minute walk to Fox in a Box.

Recently ranked the #1 Escape Room in the United States, Fox in a Box Chicago is THE place to be if you’re looking for a thrilling experience. If you don’t know what an Escape Room is...let me just say this – you could get a chance to escape a serial killer; or rob a bank (like the Joker’s entry scene in The Dark Knight), albeit within a safe and controlled environment.

Fair warning though, the games at Fox in a Box don’t work if you’re not at least a couple of people.

If you’re dropping in to Chicago, it is more or less mandatory for you to bear witness to some Chicago landmarks.

These are the places that would make it to any ‘Things to do in Chicago’ list.

Buckingham Fountain

First up is the Buckingham Fountain. Located smack in the middle of Grant Park (and in the middle of Lollapalooza!), Buckingham Fountain is one of the largest fountains in the world.

‘A Crowning Glory’ is how one visitor describes it on TripAdvisor, where the Fountain is rated 4.5 stars, by the way.

And, what makes it even more special is that during Lollapalooza, a cocktail lounge springs up at the eastern edge of the fountain.

The Bean

Next comes Cloud Gate, a.k.a. ‘The Bean’, a glittering structure made of stainless steel located in the Loop.

The exact location is 55 E Washington St, Chicago, right next to AT&T Plaza and above The Park Grill.

It’s a terrific place to enjoy the Chicago skyline from, grab a bite to eat or just sit and relax.

Is walking more your thing than to ‘stand and stare’?

Lake Front Trail

Then you can check out the Lake Front Trail, a 22 mile shared use trail running along Lake Michigan used by cyclers and joggers alike, which snakes its way through as many as 4 parks, including Grant Park.

You pass a number of well-known Chicago destinations throughout the length of the Trail, including the Navy Pier, the Museum of Science and Industry and the Waveland Clock Tower.

However, I should warn you that parts of the trail had been closed down as recently as July 22^nd due to high waves occurring in the lake.

Northerly Island Park

If you’d rather be close to a fabulous landscaped preserve, home to a lot of natural wildlife and built to simulate a natural environment, you can try out Northerly Island Park.

It’s a lot less busy than the Lake Front Trail, so if you really enjoy peace and quiet and privacy, you should go for the park.

If you’re visiting from out of Chicago, chances are you won’t have a dog with you, but I should warn you all the same that dogs are not allowed in the park, so as not to disturb the wildlife.

And if you plan on visiting at night, carry a flashlight.

Where to eat near Lollapalooza

All this talk of walking got you feeling hungry?

Don’t worry, we got that covered as well!

Lou Malnati’s Pizza

If you need to make a quick dash from Lollapalooza for a bite, look no farther than Malnati’s.

There’s a Lou Malnati’s Pizza place a 10 to 15 minute walk from Grant Park. Exit the Park where E Balboa Drive meets Michigan Avenue, turn left and walk a few minutes till you get to E 8^th Street and then you need to walk to the other end to get to Lou Malnati’s.

It may seem a long walk, but, trust me it’s not...when you realize the fact that you’ll be sinking your teeth into some of the finest deep dish pizza you’ve ever had. Prices range from $11 to $30.

Devil Dawgs

If, on the other hand, you’re on the lookout for some good old hot dogs, burgers and milk shake, exit Malnati’s and walk up S State Street for a few minutes and head to Devil Dawgs. It’s smack in the middle between Buddy Guy’s Legends and Malnati’s.

With prices in the low single digits (most items are between $3.5 to $5 and the priciest one setting you back by $7), tastes made in Heaven and a typical Chicago ambience, Devil Dawgs is THE place to be to soak up the Chicago atmosphere.

Here’s what a very recent review on Yelp says

I feel bad leaving a review because I was so full I didn't have room to try a Dawg.

Fair bit of warning though, if you are going to Devil Dawgs, be prepared to keep standing for a while. That’s because there’s often a line leading out of the front door, waiting for orders.

Enough of hot dogs, now thinking of cooling down with some ice cream?

No problem!

Gordo's Homemade Ice Cream Bars

Cross S State Street (where Devil Dawgs is), walk up W Polk Street till you get to the S Dearborn Street intersection, then walk up S Dearborn Street to Gordo’s Homemade Ice Cream Bars.

You can go for basic ice cream bars and non-dairy ice pops or paletas, or opt for composite bars like the Abuelita and the Grasshopper, plus a variety of beverages including coffees, teas, lemonade and hot chocolate.

With a 4.5 star rating on TripAdvisor and a 4 star rating on Yelp, this is an establishment you definitely cannot miss.

Bar Louie

How does dinner inside an old train station sound? Something you may look forward to?

All you need to do is head back to W Polk Street and walk for a bit towards the S Plymouth Ct till you get to Bar Louie on Printers Row.

It’s located inside the old train station in Dearborn.

Step into this restaurant and bar that’s known for being an after work destination on a Tuesday and you could be biting into one of their special $5 burgers. And one of their newest additions to the dessert menu - Churros with chocolate sauce – is getting oomphs of satisfaction almost universally.

Eleven City Diner

Now that we’ve covered a pizzeria, a hotdog place, an ice cream parlour and a bar-cum-restaurant, what’s next?

A deli, right?

And that’s where the Eleven City Diner on S Wabash Avenue comes in. You can reach it from Malnati’s via E 9^th Street and from Grant Park via E 11^th Street.

A recent review on Yelp clearly warns that if you want to dine there, you need to be really hungry – because their portions are huge. BTW, they have a 9.0 rating on Foursquare.

Whatever is your Jewish deli favorite – challah French toast, pastrami sandwiches, latkes or matzoh-ball soup – you’re sure to get it at Eleven City Diner.

Trader Joe’s

Maybe the restaurant scene has got you down, and you still want something to eat?  A Chicago day out does not end without a visit to Trader Joe’s.

Simply walk down S Wabash Avenue towards Roosevelt Road and it won’t even be 5 minutes before you’re standing in front of a Trader Joe’s.

Whether you want fresh produce or on-the-go food, Trader Joe’s is where you’ll find it.

It’s right next to a weight loss center, which is perfect if you want to do all your weight loss stuff at the weight loss center and then stock up on cake making ingredients, cheese and wine at Trader Joe’s.

Jewel-Osco

Step outside Trader Joe’s and walk down S Wabash Street past the Roosevelt Road intersection, and opposite a Dunkin’ Donuts you should see Jewel-Osco’s, another American institution like Trader Joe’s.

From avocados to milk and cheese, you can pretty much get whatever you need here, including, apparently, some items that may not be available at Trader Joe’s.

 Getting around near Lollapalooza

Transit

If you’re taking the subway

·         Harrison Station on Printer’s Row is the closest station via the Red Line

·         For the Blue Line the nearest station is Jackson/Dearborn

·         For the Green Line the nearest station is Roosevelt station

·         If you’re travelling by the Brown, Orange, Pink or Purple lines, the correct station would be the Harold Washington Library

If, however, you’re traveling by commuter rail, your options are

·         For the Metra Electric Line, you should get off at the Museum Campus/11^th Street (earlier known as Roosevelt Road Station)

·         For the Rock Island Metra Line, please alight at LaSalle Street Station

I hope you have a great time at Lollapalooza. *Drops Mic* 

-- Local Owner, Vincent Rubino with contributions from several members of the team