Home Travel A First Timer’s Guide to Eating in Chicago

A First Timer’s Guide to Eating in Chicago

by thisjess.cooks

I get asked a lot about where to eat (mabye because I’m always eating!), so I wanted to round up some of my top Chicago suggestions for you here. To note, whenever someone is visiting, I always ask if they have been to Chicago before (or New York, or whatever city we’re talking about!) because that will change what you want to do / try first.

First piece of advice, Chicago is a reservation city. You should make reservations anywhere you really want to go (and yes, some of them will be hard / impossible to get). You can get lucky with walking in and waiting for a table – especially if it’s two people, or solo dining – but if you’re a group larger than that, it’s going to be tough. Either be ready to wait enormous amounts of time (2+ hours) or make a reservation. Most restaurants book reservations through Open Table or Resy; there are only a few that don’t accept reservations at all.

If you have never been to Chicago, start with what I like to think of as “The Tourist Package.” These are the places that everyone first thinks of when going to Chicago (they do have their redeeming qualities, so I would recommend trying them once, and then moving on):

“The Tourist Package”

  • Portillo’s – hot dogs and Italian Beef
    • The flagship location located in River North is a touristy (although you’ll get your share of locals), fast-casual spot that serves up some mean Chicago-style favorites. Order the Italian Beef and definitely get the sweet or hot peppers on top. The chocolate cake is also uber decadent.
  • Lou Malnati’s – deep dish pizza
    • By no means is Lou Malnati’s the only deep dish pizza in Chicago, but it is arguably the most famous (not going to start a battle on whose is the best, either!). Point being: you can’t go to Chicago and not try the deep dish. Others to try: Pequod’s Pizza, Giordano’s, Gino’s East or Pizano’s.

Once you’ve tackled these two, an argument could be made that you need to check out Al’s Italian Beef, Garrett Popcorn, and Rainforest Café (if you have kids), but if you only have time for two meals, those are the two!


“A Local’s Recommendations”

Now you’re ready to hit some of the highlights that I really love! To be fair, I live in the West Loop, and my recommendations lean pretty heavily in that area (but for good reason, I would argue!). This is not a comprehensive list of Chicago dining, nor necessarily “the best” of everything, but if you’re looking for some recommendations from a local on places to try while visiting, this is where I would point you to!


  • Pacific Standard Time – California cooking (never can get enough avocados!), PST does a great brunch or lunch. If you can, order the Pull Apart Milk Rolls (I’m lactose intolerant, but have had others order them and they look amazingggg)
  • Somerset – a gorgeous space in The Viceroy Hotel (there is also a rooftop bar called Devereaux at the hotel, which opens at 10am on the weekends). Also good for groups.
  • 3 Arts Club Café – a beautiful space (pictured below) inside the Restoration Hardware store in Gold Coast. They don’t take reservations, but if you arrive just before 10am when you open, you likely won’t have a wait

3 Arts


  • London House – amazing views of the river and city skyline (pictured below). Sometimes there is a line to get up, but a little tip goes a long way…
  • Cindy’s Rooftop – a great way to see the lake / Millennium Park without having to be in the crowds. The wait isn’t normally as long as it may look (elevators are slow), and the views are worth it!
  • The Aviary – if you want to get fancy, The Aviary is a MUST. A swanky cocktail lounge with an intricate, molecular cocktail menu. You will need a reservation to get in here.

London House

Lunch / Dinner

  • Au Cheval – ranked as the Best Burger in the Country by Food Network, Au Cheval makes seriously drool-worthy burgers (you can get the classic Double Cheese, or get as fancy as adding foie gras). You’ll typically need to wait several hours to snag a seat in the diner, but at the West Loop location, 4 of the counter seats are walk-in only, so you can get lucky hanging around to grab one of those. Another hack? Small Cheval, in The Loop, serves the same burger with smaller wait times
  • Avec – rustic Mediterranean plates in an uber cool, minimalist space. If you’re not used to city dining (small spaces), be prepared that the majority of the restaurant is communal tables, so you’ll be sitting close to your neighbors.
  • Monteverde – fantastic modern Italian restaurant – be sure to order any of the pastas (it’s the best) and the Burrata e Ham (a classic, but again, can’t miss)
  • Aba – Mediterranean food in a modern rooftop space in Fulton Market (pictured below). They also have a rooftop patio, which you can access without a reservation if you go early
  • Izakaya at Momotaro – the Izakaya is in the downstairs of Momotaro, an excellent Japanese restaurant in Fulton Market. The Izakaya focuses on street food and drinks with a hip vibe, and a dark, cozy atmosphere. Great for a date night or with a group of friends.
  • Girl & The Goat – a Stephanie Izard restaurant, Girl & the Goat serves exceptional small plates focusing on New American cuisine (other Stephanie Izard restaurants to try in Chicago: Duck Duck Goat and Little Goat Diner)
  • Proxi – an Andrew Zimmerman restaurant, Proxi serves a small plates menu with global influences. Great for dinner, but also offers a mean brunch.


For me, the best thing to do you when you travel is eat and try new things! So happy travels (and happy eating)! If you’re looking for a certain neighborhood, or vibe, or price point, etc. the recommendations may change, but this would be my starter list! I’ll be updating this list from time to time, but stay tuned for some deeper dives into some of my favorite recommendations in the windy city!


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