my favorite places in Chicago (aka: what I’m really, really gonna miss about this place)

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As Mr. Lively, Franklin, and I gear up for our next adventure in Austin, Texas (two weeks!), I feel compelled to share all the places that I’ll dearly miss about the wonderful city of Chicago.

Though I spent the first seven years of my life in Ohio, and the following 15 in Michigan, Chicago is the place I call home.

It’s where I moved after graduation. No hesitation.

Into a tiny studio apartment, with a tiny jewelry business that I was determined to take full-time… so I could also write a book and eventually get a TV show one day.

You know, like Oprah and Maratha — “because that’s how you help people,” my 22-year-old self would assure you.

Since August 16th, 2007 I’ve had many triumphs, dark times, defining moments, and nachos.

Lots and lots of nachos.




So while I’m eager to make Austin our new home  (and perhaps even our permanent residence), I fully expect that Chicago will always be my favorite city.

… For at least six months of the year.

So rather than make a list of only the ‘must see’ and ‘must eat’ places that you have to visit if you come to Chicago, I’m going to share the places and spaces I’ll personally miss the most.

The places that mean something to me, even if they aren’t all the most dazzling hot spots (though a few of them are).

Hopefully this list will serve as a reference for those who come to visit and who live here already. 


My Favorite Everyday Eateries



Tarascas. I’m pretty sure I could have put one or two people through medical school with the amount of money I’ve spent on Tarascas’ nachos. I order them with no meat, sour cream on the side, and extra salsa. They are a weekly (sometimes bi-weekly) tradition that I’m sad to leave behind.

… But thank goodness I’m moving to the TexMex capital! (Seriously, this was one of the strong selling points for Austin/Texas in the Lively household.)


Matisse. This little bar and restaurant is my favorite spot to meet girlfriends for dinner and a glass of NZ Sauvignon Blanc. My order, which Alex (the waiter) knows by heart is the sweet pear and chicken panini with sweet potato fries (since going veggie, I order it without meat, which makes it more of a grilled cheese).


Mariscos el Veneno. Though it may seem unassuming, this (very) casual restaurant is always packed and has some of the best seafood in the city. We’ve spent many fun nights with friends digging into the family style plates of Mexican seafood with BYOB Half Acre.


Ann Sather. (Brunch) This was the first place Mr. Lively and I went to together after meeting each other the night before at a friend’s biker bar themed birthday party (true story). At the party, I asked him to be my “guy friend” and to meet me for brunch at Ann Sather’s the next day… and the rest is history. Ann Sather’s also happens to be the last place we plan to get brunch the day we leave for Texas.

Suggestion: Order anything that includes a side of cinnamon rolls!


Bongo Room. (Brunch) This brunch spot has one of the best, most creative menus out there. Definitely check out their southern location if you are visiting any museums.


City Harvest Cafe. (Green juice) This is a new organic health bar that just opened up in my neighborhood which I have been obsessed with for the last month. So much so, that I plan to get a juicer myself to recreate their Green Juice 1 and Apple Gimlet at home.


My Favorite “Fancy Date Night” Places



The Girl & The Goat. Okay, so you’ve probably already heard about this place. And for good reason. It’s awesome and – if you can get a table or spot at the bar – a ton of fun.

Tip: Make a reservation in advance.


Au Cheval. Though The Girl & The Goat gets more attention, Au Cheval is also a great (usually packed) place to go, too.


La Madia. Downtown, this is my favorite place for pizza (deep dish isn’t my thing). Get the roasted grape and taleggio pizza. It might sound weird, but you’ll thank me. Also, try their mushroom bruschetta.


My Favorite Bars & Hangouts



Matilda. Though Mr. Lively and I don’t usually go out to bars (or anywhere late at night) anymore, my favorite Chicago bar is Matilda. It’s a great local place I’ve gone to for blogger meet ups, our wedding celebration after party, Halloween, birthdays, you name it. 


Three Floyds Brewpub. Okay, so technically this place isn’t in Chicago. It’s in Munster, Indiana, about 45 minutes outside the city. But seriously, the menu is great and you can buy cases of their illusive Gumballhead beer no problem.


Hopleaf. While dating, Mr. Lively changed me from solely being a wine drinker to a hoppy beer enthusiast, too. The Hopleaf, in Andersonville, has a great selection of IPAs. My go to food order is the CB & J – Cashew Butter and Fig Jelly sandwich with sides of mac and cheese and sweet potato fries.


 (Pictured above.) This Lakeview restaurant and bar has a killer beer garden perfect for happy hour during the warmer months.


Kuma’s Corner.
 If you aren’t tired of all my burger and hoppy beer serving places yet, check out the mac daddy of them all: Kuma’s on Belmont. (They have a new location in Lakeview, but it’s just not the same.) Be prepared to wait 1-3 hours, though.


Three Dots & A Dash. Last but not least, this Hawaiian themed cocktail bar is my newest favorite place to grab a drink. Though I normally don’t like cocktails, these drinks are as pretty to look at as they are tasty to drink. Beware: lines on Fridays and Saturday nights form quickly.


My Favorite Places to Spend Time



The lakefront trail. I have lived in Chicago for seven years, always within one block of the lake because of this path. It’s a wonderful place to run, walk, bike, and take Franklin to the dog beach.

Though I’ve stopped marathon training, I still love taking long walks from Belmont to Navy Pier on Sunday mornings.


Olive Park. Truth be told, I always dreamed about being proposed to under the trees in this park. It’s settled a bit off from Navy Pier and has gorgeous views of the city.

Fun fact: I didn’t get proposed to at the park. Mr. Lively surprised me by proposing at my kitchen table in my old apartment.


Lincoln Park Farmer’s Market. I love farmer’s markets. Like churches, yoga classes, and Sesame Street, there is something so wholesome about them. The LP Farmer’s Market was a great weekend morning activity that always concluded with a Hoosier Mama scone (when they still had any left).


Ravinia. Recently, my sister-in-law began working at Ravinia, a fantastic summer concert venue in the burbs. Bring your picnic gear, coolers, bug candles, lawn blankets, and buddies.


And that wraps up my favorite places and spaces in the Windy City!

I’m sure I’ll miss these awesome places, but I also know that we may be back rather frequently since Mr. Lively still works for a Chicago-based company and his sister lives here, too.

Do you share my love for any of these places? Or do you have any other spots to add?




Tarascas photo via  |  Girl & Goat photo via  | Sheffield’s photo via.


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  1. Thanks for this! We are hoping to visit soon — I have been to Chicago a few times, but mostly for work so I didn’t get to explore much. Just bummed that we won’t be able to see you while we’re there!

    1. Aw, that’s too bad! I’m glad you will be visiting though, hopefully my list helps give you some ideas of what to do.

      Also, I love Eric’s new fade! I’m trying to get Mr. Lively on board with that cut, too. : )

  2. catfishandcaviar

    Great list! I love La Madia for some gourmet pizza and we always walk our puppies in Olive Park. I’m sure you will love Austin! I just recently visited and there are some pretty awesome restaurants and parks.

    1. Exactly! I’ve heard that a lot of Chicagoans end up moving to Austin for the similar vibe with the music and great restaurants. I can’t wait to explore it in a few weeks!

  3. jillian

    ok now youre making ME really miss chicago (for those 6 months…) so many great places! Good luck on your new adventure!! I hope you love Austin! And don’t worry, Chicago will always be just a flight away. xoxo jillian

    1. Lol, I know, right? Those six months it’s a totally different city than the other half of the year.

      And you’re right, Chicago is always a flight away!

  4. Laura @ Rather Square

    Love Hopleaf! We used to live in Lincoln Square/Ravenswood (we’re in Oak Park now), and our favorite places to eat there included Garcia’s, House of Wah Sun, and Spacca Napoli. I have a friend who just moved to Austin from Chicago and loves it. Good luck – can’t wait to hear about your experiences there!

    1. Thanks for adding these suggestions, Laura! We were totally going to consider a move to Lincoln Square next if we weren’t able to move. Love that place!

  5. What a great list! I’m glad you opted for a more personal list of favorites. I always enjoy those a bit more than the ones full of tourist hotspots or ‘coolest’ places. Especially in this case, since most of these are in my own corner of the neighborhood 🙂

    Thanks again for sharing Matisse with us last night! I’m so glad I finally found a reason to stop in after walking by it so many times, and it was great to see you one last time before you leave.

    1. Yay! It was great to see you again, too. And I’m glad I got to pass on the Matisse connection in the process. : ) See you today for the lookbook!

  6. Ah, this makes me want to visit all of these places next time we are in Chicago to see my husband’s brother and wife (in December). We usually get sushi from Coast or hit up one of the little places in Bucktown. Love Chicago, although I haven’t been there during any crazy wind or arctic temps. Wishing you guys the best on your move to Austin!

    Also, the braille necklace I got from your shop several years ago still gets comments when I wear it. Compliments and questions about what it says (dream bigger). 🙂

    1. People love Coast! I’m not sure if we ever went there or not though (I’m not a big sushi person). I should have mentioned Big Star, too! Love that place.

      I’m thrilled to hear you are still getting compliments on the braille necklace! That’s awesome. : )

  7. Also, I was going to mention that I’ve yet to pick up a pair of jean shorts (although I want to), but I have liked the Gap and JCrew jean shorts I’ve seen.

    1. Yeah, I’ve tried the Gap in my area but didn’t like the wash and cut… haven’t made it to J.Crew Factory yet, but I’m hoping to see if they have better options. : )

  8. Lisa

    Chicago is such a great city – my parents lived there, my sister lives there, I used to spend summers there and I usually visit about once a year. I even had my bachelorette weekend there! And yet, I had never heard of some of these places, so I’m glad I have new spots to explore when I visit again in a few weeks!

    1. That’s great! I’m glad you have some new places to check out when you are back in town. : )

  9. Justine Cirullo

    I hope to visit Chicago one day. These places sound wonderful!

    1. I hope you do get to come to Chicago. It’s an awesome city. Just come between June and October. : )

    1. Nice! There are so many wonderful places in Chicago, I’m sure I’ve only gone to a small percent of them myself. The everyday eateries are more ‘local’ and less maybe the kind of thing you’d find if you visited. But you might want to check them out the next time you are in town!

  10. HBahorich

    Such a great list! I love each and every adventure in Chicago. Where did you get that “IL” shirt?? I love love love it.

  11. Love this list! I just moved to Chicago and love hearing about people’s favorite spots to find new places to explore!

  12. Tomissa Porath

    I went with the boy to get those nachos this weekend and you were so right! Thanks for so many great suggestions, dear. Sorry our paths didn’t cross before you moved!

    1. I’m glad you liked them! (and that I got to pass on my Tarascas nacho obsession)! That makes me very happy. : )

  13. chantelle

    OMG this is perfect thank you so much! Just did my second move into Lincoln Park so I’m definitely hitting up lots of these places. (Ravinia is the bomb dot come. What an atmosphere!)

    1. I hope you enjoy these places. There are a lot of wonderful, everyday places to go to in LP. : )

  14. instantphoebe

    I’m really excited to try Mariscos El Veneno…Mexican + seafood? SIGN ME UP.

    What is it about Matilda that you love? I always find it to be so odd. Especially the downstairs.

    1. Jess Lively

      Yay! I hope you like MEV. Be prepared: very casual – as in, if you sit upstairs, you’re sitting on patio furniture.

      As for Matilda’s… I just love it. Perhaps it’s a personal preference thing, I just love the way it feels, it’s funky, somewhat feminine vibe upstairs, and the crowd overall. : )

  15. Danielle Reiner

    So many of these places were on my list too – we just left Chicago (for the San Fran area) at the beginning of this year. Good luck getting settled!

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