Chicago's best cheeseburgers, margaritas & gumbo to enjoy before seeing Escape to Margaritaville

Chicago's best cheeseburgers, margaritas & gumbo to enjoy before seeing Escape to Margaritaville

“Escape to Margaritaville,” the musical slated for Broadway is packing the parrotheads and other fun loving types in at its 3-week pre-Broadway run at Chicago’s Oriental Theater.

The show which is pure fun immerses the audience in a tropical island paradise with the sounds of 27 of Jimmy Buffett’s classic hits as the backdrop for three wacky love stories that take place on the island.

If you’re looking for an escape from the bad news of the day, I say GO! But don’t just go to the show–make it an evening.

Buffett’s songs are filled with food and drink references  And although Tiki Bars and gumbo are not the first thing that comes to mind when you think Chicago, you may be pleasantly surprised to find what’s out there.

Here are some of Chicago Eats dining ideas for a mash-up of the music and food from some of the songs you’ll hear in the musical.


I Will Play for Gumbo

Taken right from the lyrics of I Will Play for Gumbo, “I don’t smoke, I don’t shoot smack, But I got a spicy monkey ridin’ on my back,” Here are some of Chicago’s best spots offering this Southern favorite.

Heaven on Seven

Long time favorite, since 1985, and convenient to the theater is Heaven on Seven (111 N. Wabash on the 7th floor of the Garland Building). The Gumbo is authentic and a bargain at $5.99 ($7.99 extra large). Remember, it is cash only and the hours are somewhat limited. Dinner is only served on Thursday, Friday and Saturday. Breakfast and lunch Monday-Saturday.

Other spots where you can’t go wrong include:

Big Jones, in the Andersonville neighborhood at 5347 N Clark St (btwn W Summerdale Ave & W Balmoral Ave)–get the Gumbo Ya-Ya and Luella’s Southern Kitchen in Lincoln Square at 4609 N. Lincoln Ave., Chicago. Both are neighborhood restaurants so allow plenty of time to get to the theater.

Cheeseburger in Paradise

Photo: Carole Kuhrt-Brewer

Photo: Carole Kuhrt-Brewer

Cheeseburgers are available pretty much everywhere in Chicago from fast food drive-thrus to various gourmet takes on the original. What would Jimmy like? We think, according the the lyrics of his beloved song,

I like mine with lettuce and tomato
Heinz 57 and French fried potatoes
Big kosher pickle and a cold draught beer…

that Jimmy prefers a traditional cheeseburger at a spot where he can enjoy a cold beer and a laid-back atmosphere. Here are some spots that fit the bill:

The Billy Goat

So what better place than Chicago’s iconic Billy Goat (5 locations in Chicago–go to the subterranean one at 430 N. Michigan) to get your burger fix. Established in 1934 in a different location, the historic Billy Goat Tavern—has been on the radar of America from its goat’s curse on the Cubs to “Saturday Night Live.” The no-frills burger joint should be on everyone’s bucket list. If you do go remember to order a cheezborger. Their original is a single cheezborger on a kaiser roll for $3.35. You can also get a double, or triple cheezborger. I’d go for the single–order two if you are hungry.   

Only problem here, the hours. Perfect if you are going to a matinee but if you are going to an evening performance–you’ll have to find a way to make a day of it with lunch at The Goat, maybe followed by a margarita or two on the Mag Mile, then dinner near the theater.

R.J. Grunts

Another popular choice and longtime Chicago favorite is R.J.Grunts (2056 Lincoln Park West). This “Lettuce Entertain You” spot has been going strong since 1971. It has an extensive menu of burgers (and other dishes) highlighted by their juicy cheeseburger at $12.95 with your choice of cheese from their extensive list of cheeses. The Onion Rings at $6.50 come stacked on a stick and are spot on. Also R.J.’s Pickle Fries ($6.95) make a nice side or appetizer. If you go to Grunts, be aware, that the restaurant is several miles from the theater in the Lincoln Park neighborhood across from Lincoln Park Conservatory (2391 N Stockton Dr.)–where you may want to stop by before dinner to bask under their palm trees and large ancient ferns that grow  year round in their tropical greenhouse.

Au Cheval

A little more upscale and closer to the theater, you’ll find Au Cheval at 800 W. Randolph St. (312-929-4580). Voted the best burger in the U.S. by none other than Bon Appétit magazine, the place is cozy and smallish with a noise level that may bother some. They don’t take reservations, thus due to its size and popularity, be prepared to build in some wait time that could run as long as an hour (or longer) . The single burger actually comes with two patties with the option of adding thick-cut bacon and/or a fried egg. Personally, I think it’s just right without the bacon and egg–save those for breakfast.


“I blew out my flip flop,
Stepped on a pop top;
Cut my heel, had to cruise on back home.
But there’s booze in the blender,
And soon it will render
That frozen concoction that helps me hang on”

Here’s where to go for some of Chicago’s best margarita’s, preferably frozen?

Margaritaville Restaurant

Jimmy Buffett’s Margaritaville on Navy Pier (700 E. Grand) is the real deal with a huge selection of margarita’s and other drinks taken straight from his song lyrics such as “Who’s to Blame” and “Livin’ it Up” and as we all know “It’s 5 O’Clock Somewhere.” You can also get the one and only Cheeseburger in Paradise topped with American cheese, lettuce, tomato and pickles. As you would expect the atmosphere is casual. Click here for a look.

Frontera Grill and Topolobampa

You can’t go wrong with Frontera Grill or its upscale younger sister (as in more expensive), Topolobampa, from Rick Bayless. Bayless, knows his margaritas–having spent more that a quarter of a century serving them to thirsty visitors. The two restaurants sit side by side sharing the same door at 445 N. Clark, about a 1/2 mile from the theater. You’ll need reservations 312 661 1434.

Big Star

If you’re looking for a neighborhood joint, put Big Star in Bucktown (1531 N. Damen) at the top of your list for their insane margaritas and some of the best tacos you’ll find this side of Mexico. My favorite is their classic margarita but there’s something for everyone. In fair weather their huge outdoor patio is the place to be. At this time of the year you can chill inside in their laid back atmosphere featuring a concrete floor, wooden booths and exposed light bulbs. The prices are reasonable, with the food and vibe, just right. Big Star is about a 15 to 30 minute ride to the theater, depending upon time of the day.  773 235 4039.


When it comes to margaritas, keeping it simple is often the best course of action. River North’s Mercadito (108 W Kinzie St.)  offers a variety of margaritas, most of which are mixed with unexpected ingredients like cumin salt and almonds, but the best of the bunch, in my opinion, is a straightforward adherent to the form. About 1/2 mile from the theater.


“Smell those shrimp-
They’re beginnin’ to boil…” Margaritaville

Bubba Gump Shrimp Shack

Bubba Gump Shrimp Shack on Navy Pier (700 E. Grand) has the perfect tropical atmosphere and a large selection of shrimp inspired dishes from  their Shrimp Shack Mac and Cheese at $10.39 to my favorite, their Peel ’n’ Eat Shrimp–a big bucket for $13.49. Ten minute ride to the theater.

Margaritaville Restaurant

You can also get a variety of shrimp inspired dishes including my favorite Peel ‘n’ Eat shrimp at Jimmy Buffett’s Margaritaville on Navy Pier (700 E. Grand). Ten minute ride to the theater.

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