Chicago City Guide

Here is my guide for what to eat and do while you’re in Chicago for the Live in The Stacks tour. I have to be honest, I asked for help from two of my favorite native Chicagoans, poets Nate Marshall and José Olivarez, because yes I have a few favorite spots in The Chi, but they are truly experts.. Plus, The Stacks Pack and my BFF also provided insights to make this a truly Chicago list!


The Bean in Millennium Park
Architectural River Cruise


The Rooftop at The Godfrey Hotel
  • The Godfrey Hotel is super cute hotel! Plus, I’ll be hosting a happy hour on their rooftop on Saturday night, so if you’re in town and want to grab a cocktail, I’ll see you at the Godfrey at 5pm on August 26th.


Near Hideout
The Burger at Au Cheval
  • Pequod’s for a little deep dish moment and arguably one of the best deep dish spots in the city. If you watch The Bear, this is the spot Richie gets pizza from in his episode of season 2.
  • Mable’s Table is one of Nate Marshall’s favorite restaurants in all of Chicago.
  • Ada Street has American cuisine with a patio right down the block from Hideout, the venue for the live show.
  • Head to Au Cheval for their burger, they also have a spin off quick eats spot called Small Cheval for more burger goodness.
  • If you’re looking for thin crust pizza and chill vibes, Piece Brewery is your place.
  • Parson’s Chicken & Fish has a patio with boozy slushies and yummy hush puppies, what else do you need?
  • If you’re looking for tacos, guac, patio, and people watching, head to Big Star.
Bar Vibes
The Violet Hour
  • The Skylark is an old school dive bar that also offers some classic bar food. Heads up, they are cash only.
  • If you’re looking for hipster bar vibes, check out Scofflaw.
  • Three Dots and a Dash is a tropical tiki bar!
  • Maria’s Packaged Goods is a cool bar with great vibes, and it is attached to Kimski, a fusion restaurant (mentioned below).
  • The Violet Hour is cute and an iconic Wicker Park speakeasy. There’s no sign so lookout for a mural and a door.
Other Food Spots
The carrot cake at Hub 51
  • Hands down my favorite restaurant in all of Chicago is Hub 51, not because I have eaten much off their menu (but I do love the nachos) but because they have the world’s best carrot cake. It is arguably my favorite dessert on the planet, which is saying a lot be cause y’all know how much I love dessert.
  • José loves Kimski, a Korean and Polish fusion spot. I feel like you can’t not try that combo.
  • Timeout Market Chicago is a glamorous food court feature a bunch of Chicago staples located in a Chicago neighborhood known for food. Worth checking out for lunch to get a real taste of the city.
  • Portillo’s & Barnelli’s has hot dogs and chocolate cake milkshakes. Its a famous Chicago spot that locals and tourists love.
Gino’s East
  • I am aware there is a conversation about which deep dish place is the best. I personally have only had Gino’s East and it was bomb, but if you want to do a head to head of the two most well known spots, you’ll also need to try Lou Malnati’s (both pizzerias have multiple locations).
  • Rose Mary is a fine dining experience that is truly delish. They also have a sister restaurant BLVD which is a hip steakhouse.
  • Virtue is a Black owned restaurant with modern southern cuisine and a Michelin star.
  • Get your sweet treats from Sugar Bliss, they’ve delish cookies, brownies, macroons, and more!
  • Batter and Berries is a Black owned breakfast spot, and I’m told you must get the french toast flight.
  • Another rec from Jose is Taquerias Atotonilco located near The Mexican Art Museum.
Rose Mary


Semicolon Books
  • Semicolon Books will be onsite for the show running a popup, but their storefront will be closed due to a remodel. If you’re a Chicago local, be sure to swing by after they reopen on September 30th. They are Chicago’s only Black woman owned bookstore.
  • Volumes Book Cafe is a bookstore and cafe with two locations in the city.
  • Women and Children First is bookstore that was founded in 1979 by “intersectional trans-inclusive feminists” who “believe books are tools for liberation”.
  • Seminary Co-op is known for their large collection of academic books.
  • Here is a list of 40+ bookstores in Chicago that participated in this year’s indie bookstore day book crawl, in case you need way more bookstores in your life!

Recommendations from The Stacks’ Community

These picks were sourced from The Stacks listeners, as their favorite spots in Chicago!

HaiSous Vietnamese Kitchen