Perfect Night: Chicago. Pan Pizza and Improv Comedy.

Pequod’s Pizza and a Second City improv show make for a delicious and hilarious night in Chicago.

With exciting sporting events, world-class theater, a thriving music scene, and indulgent culinary offerings,  it’s not too hard to find things to do in Chicago at night. The only real difficultly comes in sifting through the options and choosing where to go.

For a great night out on the town, just follow this Night Out recommendation and you’ll be on your way to checking off “eat amazing Chicago-style pizza” and “experience Chicago’s famous comedy scene” from your travel to-do list.

Pequod’s Pizza

things to do in Chicago at night - Pizza at Pequod's Pizza

If you’re visiting Chicago, you can’t leave without loading up on the city’s famous pan pizza. To get your fill, get out of The Loop (Chicago’s commercial Downtown area) and head north to Lincoln Park’s Pequod’s Pizza.

A favorite local eatery and proud Chicago Blackhawks bar (the city’s NHL team for those not familiar), Pequod’s is renowned for their thin crust pizza and pan pizza. And since you can get the thin stuff almost anywhere, and since this is Chicago, you’ve got to try the Chicago-style pan pizza.

Pequod’s pan pizza is all-around legendary, but is most well known for its incredible, crunchy, and caramelized crust created by baking each pie in decades old cast iron pans. Each pie is like a thick bowl of doughy, cheesy, saucy perfection that will fill you up for the rest of the night.

things to do in Chicago at night - Pizza at Pequod's Pizza

Tip: If you’re following this Perfect Night recommendation, I’d suggest making a reservation at Pequod’s for 5:45. This will leave you about an hour to eat and enough time to take a cab to your next stop: Second City.

Pequod’s Pizza is located at 2207 N Clybourn Ave, Chicago, IL 60614. For reservations (Monday-Thursday) and priority seating requests (Friday-Sunday) call: (773) 327-1512.

The Second City

things to do in Chicago at night - The Second City Improv Comedy

The Second City is an improv comedy powerhouse responsible for launching the careers of countless comedians such as Steve Carell, Stephen Colbert, Tina Fey, and Amy Poehler. With shows 7 days a week across 3 separate stages, Second City is the premier place to spot the Carells and Feys of tomorrow.

For my first Second City experience, I chose to see Let Them Eat Chaos on the Second City main stage. At first I thought the ticket prices ($23 on weeknights and $28 on weekends) were a little expensive for a comedy show, but it didn’t take long to have me willing to pay double. I was surprised to find out that the show was more like a piece of theater (with great audio-visual elements and interconnecting story lines) than an assortment of random improv sketches.

things to do in Chicago at night  - The Second City Improv Comedy

things to do in Chicago at night - The Second City Improv Comedy

things to do in Chicago at night  - The Second City Improv Comedy

The Splurge: For an extra $10 on weeknights, and $19 on weekends you can upgrade to a premium seat.

Premium seats are those in the first row of a slightly elevated section behind general admission seating that will provide you with an unobstructed view and a little more elbow room. In my opinion, the upgrade is worth it for $10, but not for $19. Regardless of where you sit, you’re going to laugh your ass off and have a great time.
Tip: Doors open at 7:15pm for 8:00pm shows. I’d recommend arriving at that time and no later than 7:30 as general admission seating is first come first served.

The Second City is located at 1616 N Wells St, Chicago, IL 60614. Tickets can be purchased online here, or by calling the box office at  312-337-3992.

Looking To Hit Up Chicago’s Best Breweries?

Must Visit Breweries in Chicago

3 Must Visit Breweries in Chicago

Photo Credit: The Second City photos provided by The Second City

Trevor Morrow
Follow TMT!

Trevor Morrow

Trevor is a traveler, writer and video maker on a mission to help you craft the best travel experiences possible. From adventurous trips with friends, to romantic trips with someone special, to splurge-worthy trips of a lifetime, he's got you covered.
Trevor Morrow
Follow TMT!

Tags: , , , ,


  1. TomJune 4, 2013 at 6:24 am #

    Pequod’s is amazing, but I much prefer their thin crust to their deep dish… I’d rather eat deep dish at somewhere like Gino’s or Giordano’s to be honest. The sheer amount of dough used at Pequod’s doesn’t do it for me.

    • Trevor MorrowJune 4, 2013 at 8:44 am #

      Hey Tom – thanks for your comment. There are lots of great pizzas around Chicago that’s for sure (some with cheesier and saucier pies than others). I really liked Pequod’s deep dish. But for the readers out there, maybe order a small deep dish and a small thin crust so you can sample both. Another great spot for thin crust pizza is Piece Pizzeria and Brewery!

Leave a Reply

CommentLuv badge