Last month Ben and I decided to take a rather spur of the moment weekend trip to Chicago.  Our main objective was a weekend away so that we could relax without kids shouting at us or at each other.  You know…sometimes you just need a bit of silence.  We had big plans to be lazy and sleep a lot but as you will see below, we were anything but lazy.  We ended up packing a huge amount into just a couple of days.  Even though it wasn’t exactly rejuvenating, it was glorious to be able to go wherever we wanted, whenever we wanted, without worrying about babysitters or the always dicey experience of eating out with kids.  We had an absolute blast.  This is a peek into our weekend via my iPhone.  I didn’t bother taking my real camera because I knew I wouldn’t want to carry it around everywhere (or really, anywhere) we went.

It’s a quick three hour-ish drive from Indy to Chicago.  The drive was a little rainy, the first time it’s rained in far too long.  I was thankful to see the rain and hoped we were getting some back at home.

Being from Indiana, we’ve both been to Chicago many, many times before but it has usually been in the winter and usually with family.  This trip definitely reminded us what a great place Chicago is to visit.  There was of course no way we could do even a fraction of all the things we wanted to do, but we’re glad to be close enough that we can come back often.  We have resolved that we will be back again soon, and next time we may bring the kids along.  When we visit Chicago, I like to use Hotwire to find a good hotel deal.  This time we ended up at the Omni right on Michigan Ave.  It was a nice place and a great location.  We were able to walk to the majority of the places we went.  Gotta love that!

We left on a Thursday evening immediately after work, checked into the hotel, and then headed out for a late dinner reservation at Naha.  (Let me just say right now, it was a personal kind of torture trying to narrow down where we would eat during our trip.  I asked friends for recs and read waaay too many reviews and menus online beforehand.  Thankfully, choosing Naha was a stellar move.)  To be perfectly honest, Naha was my favorite meal of the entire trip.  It set the bar very high, unfortunately for the other places we ate.

We went all out, ordering our own starters and entrees, though we did split dessert.  The menu online is not completely current and unfortunately I can’t remember exactly what my entree was – I know it was fish and I know it was wonderful, but that’s it.  I blame the bottle of wine we ordered.  The rest of our meal is as follows:
Ben’s starter: Roasted Young Indiana Farm Chicken, Organic Carnaroli Risotto and Chorizo, Wood-Grilled “Bermuda” Onions, Crisp “Ruffled” Kale, Zucchini and Green Garlic
Annie’s starter: Tortellini of Sweet Peas and Cracked Blue Crab Bisque with Pea Shoots (and other things I don’t remember)
Ben’s entree: Filet of Beef Tenderloin “Crusted” with Herbs, Grain Mustard and Brioche “Crumbs”, “Hen of the Woods” Mushrooms, Veal Sweetbreads, and Green Peppercorns
Annie’s (unknown seafood) entree – it was great, whatever it was
Dessert: Bittersweet Chocolate Pavé, Milk Chocolate Beignet, Chocolate Cream and Pinot Noir Ice Cream

I really enjoyed the entire meal but the highlight for me was the starter.  The interplay of all the flavors in the tortellini and accompanying sauces was just incredible.  Overall the entire meal was superb and we’ll definitely go back to Naha.  I also have to take a moment to mention that the waitstaff was awesome.  Our waiter was very attentive without being stuffy or formal, and genuinely friendly.  Well done, Naha.  Well done.

The next morning we went for a little walk out to the lake and explored the area a little bit.  Oh, and the weather was perfect!  The weekend we were there was the first break in that insufferable heat wave we had been having.  It was nice and breezy but still sunny – just gorgeous!

One of my best friends from med school is currently in his residency in Chicago, so we spent a lot of time with him.  We met up Friday morning and he took us to Bongo Room for brunch.  Dudes, it was awesome.  I had such a hard time deciding what to order, and am planning to recreate basically every dish I didn’t order because the menu was that good.  Eventually I settled on an omelette with chorizo, potatoes, and avocado.  It was very good but totally massive and really enough for two people.

That was great fuel for the morning of shopping that followed.  We walked around Michigan Ave. and browsed a few stores, and ended up at J.Crew.  Surprise, surprise, and time well spent, Annie.  Seriously, we have one in Indy but I’m just drawn to them!  I did end up with quite a few great finds there so I guess it was worthwhile.

Then, though it wasn’t exactly right nearby, I insisted that we walk over to a Paper Source store.  I’ve been ordering things from Paper Source for years and have always, always yearned to see one of these stores in person.  It was even more fun than I had imagined and I was on excitement overload at that point.  I could have stayed there all day but I don’t think Ben felt quite the same, so we headed back to the hotel.  I had a quick catnap and was excited to get moving again but Ben took the longest nap in the history of the world.  Maybe not really, but I was just so ready to go out and keep having fun!

Eventually when my patience ran out and tapping my foot got boring, I woke Ben up and announced we were going to XOCO.  We definitely wanted to eat at one of Rick Bayless’s restaurants and the quick, low maintenance approach of XOCO perfectly fit into our plans that day.  (Funnily enough, this is actually diagonally across the street from Naha.  There’s some good food at that intersection, my friends.)

XOCO has an amazing variety of tortas and, once again, it was an incredibly tough decision figuring out which one to order.  I ended up getting one with garlicky shrimp, caramelized onions, arugula and goat cheese.  It was fabulous.  I believe Ben’s had chorizo, poblano, artisan Jack cheese and came with tomatillo salsa.  And while the tortas were great, the highlight for me was the churros.  If I could, I would go back to Chicago for one right now.  Not even kidding.  My mouth is watering just thinking about it.

After XOCO, we hightailed it over to the Terrace bar at Trump Tower to meet my friend for happy hour.  Now let me say right off the bat, I wasn’t sure what to expect of this place.  I guess I had kind of a negative mindset about it being associated with the Donald and all, but this was a pretty awesome experience.  It was just a really beautiful, relaxing atmosphere and the cocktails we tried were all great.  Sitting and talking while taking in the blue skies, Chicago skyline and great views of Lake Michigan – it was just wonderful.

As a bonus, you can get a picture where you look kind of moronic as you are blinded by the sun.  Wahoo!  (On that note, if you go – wear sunscreen!  I did not have the foresight to do so and got a very interesting burn from my lace-backed Anthro dress.  Yeah.)

After happy hour, Ben and I wandered around a little more and then headed over to mk The Restaurant for dinner.  Our meal at mk, while very delicious, was not quite as magical as the evening at Naha.  I don’t blame the restaurant though, but rather the woman at the next table talking in the loudest voice ever, mostly about her childbirth experience.  Really, it was so bizarre I kept looking around to see if maybe it was some kind of hidden camera situation or if we had stumbled into an SNL skit.  Everyone else at her table was speaking in normal voices but wowza, she was on a whole other level.

As for the meal itself, we thoroughly enjoyed it.  We both did the tasting menu and, just like Naha, I did not take notes afterward and therefore have spotty memories of the specifics of the meal.   I completely forget the starters.  Dang!  The first entree was a whitefish that was probably my favorite part of the meal.  It was perfectly cooked and served with a parsley puree and glazed baby carrots.  The next dish was a steak (forget the exact cut) and it was mouth-wateringly good.  We ordered the optional pommes frites on the side because they really shouldn’t be optional.  It was another wonderful course.  The meal finished off with blueberry crisp for dessert.  Other than the neighboring diners, it was a lovely.  The service was impeccable, and only later did we learn it was actually our waitress’s first night.  She did a great job!

The next morning was another highlight of the trip for me.  Finally, after countless emails, I was able to meet up with my blogging buddy turned good friend Elly of Elly Says Opa.  We met for breakfast at Yolk, a restaurant we have loved since our last visit to Chicago.  I had the French toast sampler and it was great, but I was really having too much fun visiting with Elly to think too much about the food.  She is just a lovely person, and so much fun!

Ben finally bought himself a pair of sunglasses and we decided to take this photo on our walk back.  I laugh every time I look at it.  We just look like two…I can’t even think of a polite word to say, so I’ll be quiet now.

After breakfast we had a short little block of time to kill so we headed down Michigan to visit the Art Institute.  This is one of our favorite places in Chicago and it’s a must every time we visit.  We didn’t get to stay long this time but I made a beeline for my favorite part, the impressionist area with all the Monets.  My mom really loved Monet, particularly the water lilies, and she bought me lots of books about him when I was little in hopes that I would be interested too.  Now whenever I see them I think of mom.  I always stand in this room tearing up for a little while.  I wish we could have seen them together.

On our way back up Michigan we made a super quick stop at the bean because, believe it or not, in all our previous trips to Chicago, neither of us had ever been there.  I just wanted to see it in person.  Tourist!

We met up with my friend for an architecture tour on a riverboat.  I have mixed feelings about this.  It was a nice experience visually and I learned a few interesting facts but it was just a tad on the dull side for us.  I’m sure lots of people just love this but it really wasn’t my thing.

After a quick caffeine pitstop, we made it over to show at The Second City comedy club.  If you aren’t familiar with Second City, this is the starting place (or jumping off place) of many great comedians.  We have always loved improv comedy so I knew this would be a great time and it was even better than I had hoped.  The current show (“One Nation Under 1%“) is absolutely hilarious.  We laughed from beginning to end.  I’ll definitely do this again next time I have the opportunity.

After Second City we had dinner at a restaurant that was just okay at best and so I won’t be reviewing it here.  You can’t win them all, I guess!

The next morning was Sunday and that meant saying goodbye to our fun weekend.  Before leaving, we walked over to Yolk again for breakfast and on the way passed this truly amazing building that we had seen several times in our earlier walks around the city.  It’s the Poetry Foundation and it is just something you need to see in person.  I wish we had had more time to explore because all those books were just calling to me.  I could spend hours or probably days in a place like this.  Next time I’m checking this place out more.

And then we went home, and back to reality.  Bye Chicago.  It was fun.

  • Mary Beth

    Love Chicago! We were there two years ago and ate twice at a little gourmet wine/cheese/sandwich shop called Pastoral. I still dream about eating their Blue, Pig and Fig sandwich!

  • Kristin

    Growing up in Madison, Wisconsin, I have always had bad feelings about Chicago…it meant Chicagoans coming to our state parks & misbehaving or loooong endings or beginnings to car trips that required getting around the city. This post has definitely shown me another side to the city, and has made me think I might want to visit. Thank you!

  • Samantha

    I recently moved to Chicago from Lafayette, In. I love it here and the food is amazing. Bongo Room is right down the street from me. I will be checking out some of the places you mentioned! I also recently did the architecture tour. It was my 2nd (2 different companies) and the Skyline company’s tour was funny and interesting so it didn’t get boring. Plus it was sunset so it was gorgeous!

  • Annie @Annie’s City Kitchen

    What a lovely trip! I live in Chicago (born and raised) and it makes me beam with pride whenever someone else loves the city too (or when someone loves Bongo Room!). I can’t imagine living anywhere else and I’m so glad you enjoyed your weekend.

  • Emily @ She Makes and Bakes

    What a fun trip! I’ve only been to Chicago for a couple of days, but it’s a great city. I definitely want to go back, too!

  • Susanna B.

    Looks like an awesome trip for the two of you! …And so much yummie food! …And great pics! My sister lives in Chicago but it takes 12 hours for us to drive there. But it is time to go…maybe Thanksgiving?

  • annieseats

    Oh yeah, you definitely need to visit. There are so, so many wonderful things about Chicago. I love it there!

  • Marsha

    Chicago is always a great place to visit. Next time you will have to take a tour on the Wendella Boats. They have a great architecture tour, sunset tour and tour around the lake. There is also a company out there that does a walking food tour which is really fun. Enjoy your next trip and thanks for your recipes.

  • Louann

    Living in Chicago, we tend to take a lot of it for granted, but I LOVE this town. It is so beautiful and there is so much to do and see and soooo many great places to eat. I hear Indy is a great place to see, too. We’ll get there one of these days.

  • cindy

    My daughter lives just north of Chicago so we visit often. The city has so much to see. One summer years ago we too our 5 children ages 8-20 to visit their sister. What a trip! We went to a Cubs game, did The Taste of Chicago and watched the 4th of July fireworks (with 2 million of our best friends)! All in one long day like 7 AM to 3AM. It was quite a culture shock for our little raised in small town UT family!
    My kids still talk about that trip today!
    My hubby loved the architectural boat tour but he draws bridges for a living. He was taking photos like a crazy man of the undersides of the bridges!
    Now when we visit Chicago we mostly just want to kiss our Grand kids! I’m sure as they get older we will do the Cubs, Aquarium, Field Museum etc.again.

  • Kelsey

    What a perfect weekend! I am so jealous of everything–the food, the art, the architecture, and of course, Elly! It looks like you and Ben had a really fantastic time. Well deserved, too!

  • Caroline L.

    You certainly had a jampacked weekend, but it looks like you had soo much fun!

  • You should go on vacation more often so you can write more great posts like this! Loved reading about your trip.

  • Adrianne

    I love Chicago! A high school classmate of mine has done shows at Improv Olympic near Wrigley field, a very fun place. You should check it out next time you’re in town.

  • Mie

    Wow, even you iPhone photos ends up beautiful ;-) Looks like a great trip. Chicago is definitely on my to-do list!

  • What an awesome trip! I have always wanted to go to Chicago! I am a big city kinda girl. :) The food you tried sounds amaaaazing! I am super jealous of that french toast sampler, and your tortellini!

  • So glad you guys had such a good time, and got to eat some good stuff, too. :) Can’t wait till you come back! Next time, we are so going to get the hot chocolate at XOCO (yep, totally invited myself to hang with you at XOCO).

  • Denise Wesely

    What a wonderful review of your trip. Now I have to get hubby to take ME there. Son and daughter-in-law go there occasionally for marathons……and the food! I have to ask, what was the white sauce served with the churros? I believe I detect vanilla beans in it? Thank you so much for “taking us along” on your trip.

  • Brittany – Life of a Bama Girl

    I went to Paper-Source for the first time in Georgetown today. I’m even more in love with it now.

  • Leah

    It sounds like a great weekend- I would like to visit Chicago, and if I ever do, I will be looking to this post for restaurant recommendations. Also, where did you get that shirt in that first picture of you?

  • Maia

    Thanks for sharing this!! I have a trip planned to Chicago at the end of October and it’s so helpful to hear your recommendations! I’ve never been before but grew up loving the Chicago backdrop in ER. Looking forward to taking in some of the sights you’ve highlighted, and it sounds like Naha is worth a visit too!

  • annieseats

    That was a ModCloth find :)

  • annieseats

    It is actually vanilla ice cream. So, so good. They are often served with chocolate dipping sauce but given the heat that day, the ice cream was the way to go. I’ll have to try the chocolate sauce this fall or winter :)

  • annieseats

    Um, YES.

  • Amy B @ Second City Randomness

    Bongo Room is my favorite breakfast spot in the city. I’ve been there several times and it’s crazy on the weekends, but totally worth the wait!

  • I love Chicago so much, I went there for an orchestra competition and have so many fond memories associated with it. We did allll the touristy things :) PS. paper source is AWESOME!

  • Elizabeth

    I lived in Chicago for five and a half years and it will always hold a soft spot in my heart. It’s the place where I was able to spread my wings and where I met my fiance. So glad you had a fun weekend.

  • katy

    So fun! My husband and I are trying to plan a long overdue getaway too (before baby #3 arrives). Wish we were close to Chicago, but Nashville might do. There are some wonderfully magical children’s books by James Mayhew – “Katie Meets the Impressionists” and “Katie and the Water Lily Pond.” I love reading them with my 4-year-old daughter, and thought you’d enjoy them if you haven’t seen them before.

  • Allison

    my husband and I visited Chicago last month for just 2 days. Wish I had more time to do sightseeing and explore places to eat. Glad it was a fun trip for you and your hubby too.

  • Runt

    Wow, that all looked like a blast! As I was reading I was trying to count how many restaurants you went to versus how many days you were there. I lost count but it sounded like a lot – haha! NY is definitely on my bucket list and I think you just made me add Chicago too! =]

  • Her Late Night Cravings

    Love being a part of your trip especially since I’ve never been to Chicago!

    Jayme @ Her Late Night Cravings

  • annieseats

    When you are staying in a hotel and eat three meals a day out, it adds up quickly.

  • annieseats

    Thanks for the recs!

  • Thank you so much for the review! My boyfriend and I are planning a road trip and one of our stops will be in Chicago. I’ll definitely have to refer back to this later when planning our trip! Also, what was the name of the restaurant that was just ok?

  • Deb C

    Yolk, Xoco, Bongo Room…love them all! One day in the near future I will have to try Naha.

  • Morgan

    oh man, the poetry house is 2 blocks from my apartment! would have loved to meet you. that probably sounds creepy considering i’m a complete stranger, haha!

    next time you’re here you have to venture out to tweet for brunch. it’s a little farther north in Chicago but completely worth it! old town social (a few blocks from second city) has a pretty fantastic bloody mary and brunch if you’re into that sort of thing :)

    glad you had a nice visit! cheers and happy eating!

  • Stefanie Squier

    yolk! i remember some friends of mine talking about this place a few years ago and i had forgotten all about it. i’m visiting chicago on monday and we’re staying half a mile from one of the locations. helloooo breakfast every morning! this post was just perfect timing for me :) thank you!!

  • Gail

    OK, I couldn’t help myself, when I saw the “We stayed at the Omni,” I thought, “Guests of the Oprah Winfrey Show” (and then got jealous! haha) I’ve always kind of dogged Chicago, but this post reminds me that maybe next year, Nick and I can take a little vacay from the baby and head up there to check out some of these amazing restaurants!!!

  • nmtowell

    I just visited that Paper Source location yesterday during my own Chicago trip! 2 floors of lovely paper & goods!
    If you’re ever in Lincoln Park you should try visiting Toast for brunch. They have great french toast!

  • annieseats

    Oh yeah, you would love Chicago I think. There is so, so much great stuff there. I feel like we could go every month and not get to it all!

  • annieseats

    That’s awesome! I am obsessed with the poetry building. Every time we walked past, I wandered around that outdoor area just in awe. I’m not a bloody Mary person but I do love brunch. Thanks for the rec!

  • MeL

    Sounds like a fantastic trip! Can’t believe you took all those great pics with just your iphone. Is that just using the regular camera or are you using any special camera app(s)?

  • Kathleen

    Oh yeah! You have to try the chocolate sauce next time. It’s so good I eat it with a spoon after I finish dipping my churro in it! Glad you enjoyed Chicago… You hit some of my favorite places!

  • Jennifer Black

    Love the aviator picture… ballers :)

  • Lindy Fischer

    You hit up so many good spots while you were up here! I’m really glad to hear you loved Naha. Marcus had the chef put on one of his food and wine dinners that he did last year for work. Your iPhone pics turned out pretty sweet. I’d say it was a perfect weekend in the city for you two! I was jealous and I live here, haha!

  • annieseats


  • annieseats

    I was thinking more like d-bags, but you know…same-same ;)

  • annieseats

    This is a mixture of Instagram and Camera +.

  • Julie @ Table for Two

    I can’t wait to visit Chicago again. The last time I went it was a horrible time. It rained the entire time and was super cold. I guess I should’ve chosen a better month to go. I didn’t go to the Bean either so that’s definitely something I want to do next time I go. You are so adorable and I love that aviators picture! Haha, thanks for sharing this trip with us! :)

  • mariseashell

    Thanks for all the tips…perfect timing. I can’t wait to go to Chicago with my husband next month for my birthday weekend celebration and experience a few of those restaurants!

  • What a fabulous trip – you packed in so much! We lived in Chicago for 7 years and I really miss it. I’m jealous about your trips to Bongo Room and XOCO!

  • Kristin Key

    oh man. i’d love to see you recreate lemon ricotta & sour cherry hotcakes or raspberry oreo flapjacks! :)

  • annieseats

    I have a recipe for lemon ricotta pancakes posted. You can find it via the search bar :)

  • Stephanie

    Looks like a great trip! Chicago is one of my favorite places to visit. Next time I go I’d love to go to some of the places you mentioned

  • lara tickle

    so glad you went to XOCO! anytime i know anyone going to Chicago i tell them to go there. SO YUMMY!