Trains, Planes, and Vino

Before spending 8 years in New York City, I lived the majority of my life in Chicago and the surrounding suburbs. I was born and raised in South Suburban Chicago and, after college, lived in the city for 5 years. I return to Chicago at least once a year to visit friends and family and, for the most part, love making the trip home (it just depends on the weather!)

But what I love even more is telling people about how wonderful of a city Chicago is. I love sharing my favorite things about the city and encouraging East Coasters to check it out. I’ve also found from traveling abroad that most foreigners prefer Chicago to New York if they have visited both.

What is so special about Chicago? It’s far more livable of a city than New York, but offers many of the big city amenities. There are incredible, world-class restaurants as well as famous hole-in-the-wall spots serving up delicious local food. It’s a city of neighborhoods, similar to Brooklyn in some ways, and it’s worth getting out of Downtown Chicago to explore. I highly suggest to everyone visiting that they jump on the L and go exploring – it’s the best way to get a glimpse into the true spirit of Chicago. (Taking the Brown Line is probably my favorite – I love how it weaves around trees and past the rooftops on the North side like an amusement park ride.)

The city really comes alive in summer and it’s worth considering a first time visit between May and September. There are street festivals all over the city every weekend, and the lakefront is one of the best places to be on a hot summer day. Chicago is a city that really shows off during the warmer months and the people that live there wait all year for Chicago summer to arrive.

If you manage to visit when it’s not so nice outside, there is still plenty to see and there are places to escape the cold and the wind. Besides, if you survive a few winter days in Chicago, you will have something to talk about after your trip (and a reason to come back during the warmer part of the year!)

I want to share some of my favorites, even though many of them may feel “old” since I haven’t lived in Chicago proper since 2010. I generally go to my old favorites when I come back to town, or I ask my friends to suggest some new, cool spot worth checking out. It’s always a shame to learn when one of my favorites has closed, but it’s far more common for that to happen in New York than in Chicago.

Since it’s a city of neighborhoods, I’ve offered suggestions by location. I’d also suggest staying in an Airbnb or a hotel outside of The Loop/Downtown in order to really get a feel for the city. Most of the recommendations are based on the areas where I used to spend a lot of time or where I lived. For more recos across the city, definitely check out sites like Time Out Chicago, Thrillist, The Infatuation or Eater Chicago for the latest.

Wicker Park/Bucktown

I lived in this area from 2006-2008 and it has changed a lot since then. I still have a few friends in this area so manage to come back every time I am in Chicago. Generally I walk around calling out what places are new, what is long gone, and am shocked by the old haunts that have not been displaced.

Near Division (Between Milwaukee and Damen): There are so many new places on Division – I don’t even recognize this area anymore!  

• Milk & Honey – Great brunch/breakfast spot
• Smoke Daddy – Come here for the BBQ and live music
• Happy Village – A cozy neighborhood dive bar. This used to be my voting location!

There are also a ton of dive bars in this area, some more hipster than others (if things have not changed much since I lived over there)

North/Milwaukee/Damen area – This is the heart of the Bucktown/Wicker Park area. Lots of shops and restaurants. Some of my favorite vintage boutiques are on Milwaukee. There are higher end shops on Damen north of North Avenue.

• Handlebar – Good veggie friendly spot
• Piece – Pizza and brewery. Specializes in New Haven style pizza so a nice change from traditional Chicago styles. Always packed
• Big Star – Good taco spot. Great people watching. Great drinks. Good for day drinking or just hanging out.
• Violet Hour – the OG speakeasy bar in Chicago, across the street from Big Star.
• Map Room – Great beer bar, big selection
• Coast – Good sushi spot and it’s BYOB. Reco the White Dragon if you go!
• Dove’s Luncheonette – Tex Mex diner, very popular for breakfast
• Bongo Room – Popular brunch spot, always pretty busy. Specializes in over the top breakfast items.
• Hotel Robey is a new hotel at this main intersection, have a rooftop drink and some tasty food
• Louie’s Pub – My go-to karaoke bar when I lived in Chicago. Always a good time.

Logan Square

At the time when I lived in Chicago, this neighborhood was still up and coming. It is now fully gentrified.

• Longman & Eagle – Both a restaurant and a B&B
• Lula Cafe

Lincoln Park

I lived here for the first year after college. Proximity to the lakefront and the park is the upside. Beautiful homes to stare out. Tends to be a little fratty.

• Summer House Santa Monica – Enjoyed a late dinner here on a Sunday, imagine that it is packed for brunch
• Alinea – The most famous restaurant in Chicago, possibly the world. Good luck with a reservation 🙂
• Check out a show at Second City or another improv show (like I/O)
• Go to the Lincoln Park Zoo / Conservatory. During the holidays, the Zoo hosts Zoo Lights which is pretty fun to check out
• Kingsbury Street Cafe – Perfect for brunch
• Kingston Mines – If you like blues, definitely check this place out. It’s open very late so you can find time
• Jaimito’s Burritos – My favorite hole in the wall spot for late night nachos 🙂

Lakeview/Wrigleyville

You are likely coming here because you are going to Wrigley Field. The bars along Clark are insanely fratty. Keep that in mind if you enter any of them, especially on a game day. Going west towards Southport is a good bet, the neighborhood is a little more chill. The other option is to go east towards Broadway between Belmont and Addison (partially known as Boys Town) which has more shops and restaurants. 

• Southport Grocery – Always good for breakfast (and cupcakes). Eat outside and people watch if the weather is nice!
• Hit the lakefront trail for a run, walk, or bike ride. It extends far south towards the Museum Campus and far towards the north side.  All of it is beautiful!
• Frasca Pizzeria – closer to Roscoe Village, perfect for drinking too much wine with friends
• Dinkel’s Bakery and Wishbone North for breakfast
• Guthrie’s – Across the street from my old apartment, this cozy bar is perfect for hanging out on a crap weather day in Chicago. Bar is stocked with old board games and beer of course

Fulton Market/West Loop

This area has grown a lot since I lived in Chicago and a lot of the top restaurants are in this area. I really love this part of town and enjoy coming back here to see what is new. There is now an Ace Hotel in the area, as well as Soho House.

• The Publican – Popular for its chicken and its beer. Good for brunch as well. 
• Lone Wolf – Cool bar, good for waiting for your table at Au Cheval
• Au Cheval – The most famous burger in Chicago. There’s also a Small Cheval now on Milwaukee in Bucktown and one in Old Town on Wells St.
• Girl & The Goat – very popular restaurant
• Maude’s Liquor Bar – French restaurant with terrific cocktails
• RPM Italian
• Little Goat Diner (For breakfast)
• Avec – This place is always good (as is

The Loop

While I would typically stay away from this area if I were visiting (it is very busy during the weekdays and pretty dead on weekends), you may find yourself here to do some touristy things like taking a selfie in The Bean or going ice skating at Millennium Park. On a few recent visits I have discovered some great hotel bars around here that I would definitely recommend.

• Raised (at the Renaissance Hotel)
• Cindy’s (at the Chicago Athletic Association)
• Check out the restaurants along the Chicago River like City Winery, especially on a hot day
• Visit the Art Institute and then swing through Millennium Park
• Take a riverboat tour – Highly recommend the architecture tour (there are a few companies that offer these)
• Take a trip up to the observation deck of the Sears Tower (aka Willis Tower). I haven’t done this since I was in elementary school!

River North

• Ema – Just recently tried this spot and had an incredible dinner. Mediterranean, small plates for sharing. Everything is good!
• Frontera / XoCo – Rick Bayless’s restaurants are some of my favorite in Chicago. Xoco is good for quick sandwiches, Frontera is great for a nice lunch or dinner.
• Quartino – Small plates Italian, always a good spot

Gold Coast/Upper Michigan Ave

• For a truly spectacular Chicago dive bar experience, check out the bars around Rush & Division. My personal favorite is The Hangge-Uppe 🙂
• Check out the Museum of Contemporary Art – It’s just east of Michigan Avenue and one of my favorite places to visit in the city. They have a new restaurant in the lower level, Marisol, which is delightful for a post-art drink/lunch.
• Have a drink at The Signature Room at the John Hancock building. The drinks are overpriced and the snacks are terrible, but it’s worth it for the views (especially the view from the bathroom).

Chicago Essentials

Food: There are a few foods that come to mind when thinking about Chicago. Eat at least one during your trip.

• Pizza – I am a deep dish advocate, but I generally love all sorts of pizza. Chicago is also known for a thinner crust style and would suggest trying at least one style (especially if you are a New Yorker and think no pizza is better than NY style pizza)
  • Deep Dish: My fave is Gino’s East. Many people are partial to Lou Malnati’s. Also, Giordano’s is great. You will not go wrong if you try any of these 3 spots.
  • Non Deep Dish: Piece, Spacca Napoli, Pequod’s
• Hot Dog: Order your Chicago dog (look for the neon Vienna Beef lights). Do NOT order it with ketchup. My reco is for Portillo’s, but you can generally get a good one anywhere (Gold Coast Dogs is another popular spot). If you want a truly entertaining hot dog experience, visit the Wiener Circle in Lincoln Park. This place is a shit show at night – watch out for people ordering Chocolate Milkshakes. The fries are crazy good and greasy.
• Italian Beef – I was never really a fan of this, but it’s pretty popular and I guess it’s good if you get it from the right place. Check out Portillo’s or Al’s.

Check out a ball game when you are in town if it’s during the summer – either take the Red Line to Addison and historic Wrigley Field for a Cubs game or take it in the other direction towards 35th Street for a White Sox game at Comiskey Park (ok it’s called Guaranteed Rate Field now which is just awful). If it’s not baseball season, look into tickets at the United Center for a Blackhawks or Bulls game. OR, just find a sports bar (there are MANY) and enjoy the game like a local.

And one last thing – Don’t go to Navy Pier!