Travel Diaries: Chicago with Jess Keys

Jess Keys ChicagoTell us about yourself!

I'm an Enneagram 7 wing 8. My husband Neal and pandemic baby girl, June, are my two favorite sidekicks. We live in Chicago and love to travel. My background is in advertising, where I worked for four years before leaping into the world of self-employment. Many years of lost sleep and ramen noodles later–my hard work paid off, and my blog is my full time gig. I wouldn't have it any other way!

I’ve never met a french fry I didn’t like. (Unless, of course, it was soggy.) I love cooking, reading, singing, playing the ukulele (my pandemic project) and if I had endless funds and spare time, I would use it all to travel to as many places as I could! (And maybe buy a flat in Paris.)

Where did you grow up/ How did you wind up in Chicago?

I was born in Oregon, where my whole family is from. We moved to Scottsdale, AZ when I was in middle school and I finished out high school there, and then decided to go to the midwest to Indiana University Bloomington for college. Many of my friends I met there were from Chicago so I spent several weekends/school breaks visiting friends there and decided it was the most logical place to move post-college, since so many of my friends were doing the same!

What is your favorite thing about Chicago?

So hard to choose! I think the people are really wonderful here. Everyone is really nice and down to earth. Also–the food and bar scene here is so good. I think we really take for granted how good we have it.

jess keys chicago
Any fun facts about Chicago that most visitors wouldn’t know?

Every neighborhood of the city is so different and has a totally different culture/history. There are 77 neighborhoods that make up Chicago and they’re all like their own little worlds, each with a different flavor. Most visitors don’t get past downtown–I always encourage visitors to get out into the neighborhoods so they can see how unique they are!

Now for all your tips. What is on your “Best of Chicago” list?

Best Accommodations: The only hotel I’ve ever stayed at in Chicago is the Waldorf for our anniversary staycations–which I highly recommend!

If you’re in Chicago for a vacation and aren’t super familiar with the city, I recommend staying in the Gold Coast. It’s a great location with great shopping, amazing restaurants, great people watching, and it’s pretty centrally located so it’s an easy Uber to more western neighborhoods and Northern neighborhoods.

I live in Wicker Park and there is a ton to do around here as well–The Robey is a really cute hotel over here. West Loop is also a good option as you’re in the hub of the some of the best restaurants in the city!

jess keys chicago
Places to Play: June is only a year old so I am not super well versed in this, but the Lincoln Park Zoo is free and a great place to walk around with kids! Or try Millennium Park, Navy Pier, Shedd Aquarium or the Chicago Children's Museum.

Best Places to Eat: For date night/dinner with friends–these are all tried and true favorites for visitors and locals!

  • Boeufhaus: Boeufhaus is known for their steak, but they have a really amazing farm to table menu. The bar truly is the best seat in the house, as you can watch the chef and kitchen staff working their magic in the kitchen, and the bartenders are always phenomenal. Highly recommend the seasonal market salad (usually a plethora of shaved vegetables tossed in a magical goddess dressing–it’s so good. How can a salad be so good?), the ribeye, and the sides are always amazing–especially the polenta and the frites. Also don’t miss the au poivre sauce for the steak.
  • Heritage Restaurant + Caviar Bar: This place is an absolute GEM. It’s a little off the beaten path, it has remained a bit of a neighborhood secret. It’s a chic (but very unstuffy) space with an awesome bar–which, of course, are the best seats in the house. They have an Eastern European focus to their food, in addition to, of course, caviar! The bartenders are a key part in making it such a wonderful experience–this is the kind of place where you feel like a regular after your first time visiting. Don’t miss their cocktails with house-made shrubs, or their house-made dumplings!
  • Gemini Bistro: I lived across the street (above Four Farthings) for years in my early twenties, and my roommates and I would always scrape together our money to sit at the bar and split steak frites for dinner. It was the best then, and it’s the best now! They make the best sidecars in town, too, by the way! The bar service is always top notch. Best seats in the house! A Lincoln Park favorite.
  • Girl & The Goat: You may wait weeks to get a reso at Top Chef Stephanie Izard’s most famous restaurant, but the secret is to walk in and grab a seat at the bar! GTG has never disappointed, and has remained a West Loop icon since it opened years ago!
  • Bavettes: Known unofficially as the best steak in the city. (Totally rivals Boeufhaus–I think it’s a toss up, IMO). If you want a nice, swanky steakhouse, there is no better place than Bavettes!
  • Armitage Alehouse: An English pub, but very swanky, with amazing cocktails and super unique English/Indian fare. Just tried this spot recently and it was some of the best food I’ve had in SO long.
  • Ada Street: Another go-to favorite of ours. Their farm to table menu changes seasonally and I’ve never had a less than incredible meal here! It’s dark and candlelit which makes it extra cozy in the winter, but they have a big garage door they open in the summer to make it breezy. Their wine selection is amazing and unique–have your server make recommendations for you. Yes, it is in a bizarre location in a middle of a bunch of warehouses behind Home Depot, so don’t worry–your Uber driver isn’t taking you somewhere to murder you.

jess keys chicagoWith kids:

Our go-to’s are The Perch in Wicker Park or Parlor Pizza (they have multiple locations). Colectivo is great for coffee and a pastry (they have high-chairs!)

For a longer list of reader recommendations by neighborhood, check out the roundup of favorite kid-friendly spots here!

Best Shops:

  • ALICE & WONDER: Of course, you know Alice & Wonder had to be at the top of my list! My friend Ali (who I collaborated with on the VOTE and Mama tees!) is the one that makes the adorable Chicago sweatshirts, tees, hats, and accessories, but she also has tons of cute women’s clothes, gifts, cards and more!
  • VIRTU: One of my absolute FAVORITE stores to pop into in Bucktown. I think I could knock off my entire shopping list in Virtu alone. You will want to buy one of everything–they have a lot of special things you wouldn’t normally find elsewhere–like amazing ornaments, tons of cards, paper goods, ceramic pieces, you name it. Their owner Julie is so nice and can help you find the perfect gift. Plus, a really cute shop dog named Mochi!
  • THE RED BALLOONThe CUTEST place to buy gifts for little kids! They have clothes, toys, books, and more. Voted the #1 children’s store in Chicago!
  • ART EFFECT: This store will always have a special place in my heart because it was just a few doors down from my first apartment, and has always been a Lincoln Park favorite. They have something for everyone here, from women’s clothes, to jewelry, to cute knick-knacks, cocktail essentials, beautiful coffee-table books, candles, housewares, cards and more. This is where I would always go to shop for a gift exchange. (Remember those?)
  • P.O.S.H: Last but certainly not least, this list would not be complete without P.O.S.H. I absolutely adore this store full of vintage and new French housewares, books, and other goods. It’s basically a well-curated Flea Market boutique! Any Francophile will flip over anything you find here. I especially love their little bitty bistro wine glasses that we use all the time.

Best Grown-up time Entertainment:

Catch a broadway show (there are always several!), or see some live music at The Empty Bottle or California Clipper!

Best hidden gems / Spots that locals love?

I think all the restaurants/shops above are definitely local-approved, but one tip I always give people is to get out of downtown and admire the skyline from a different perspective–the Robey’s rooftop in Wicker Park is unique in that it’s one of the few rooftops you can see the skyline from the west, and same with the J.Parker in Lincoln Park where you get lake views and skyline views from the North. Another local tip: You can get in almost any restaurant you want if you walk in and wait for seats at the bar, even if you can’t snag a reservation. The best time to do this is either at 5pm or after 9pm!

Also, if you’re in Chicago in the summer, every local will tell you that this city is king of patios. I have a whole blog post with 50+ favorite Chicago patios here!

And finally, what’s next on your travel bucket list!?

My husband and I are heading back to Ireland in July, and I’ll be heading to Portugal with my friend in August! I can’t wait!

jess keys chicago

Leave a comment

All comments are moderated before being published