our midwestern adventure

We had such a great time in the Midwest!

Nothing like braving ten degree temperatures and seeing all the lights on Michigan Avenue to get you in the Christmas spirit! We also were able to score last minute tickets on Craigs List to Bon Iver in Chicago, which was AWESOME. Bon Iver is one of my very favorite bands and seeing them live has been a bucket list item forever for me.

We both were able to catch up with old friends in Chicago and then rented a car and drove to Milwaukee to visit my grandparents, which was the whole point of this trip. Just seeing the look on my grandpa’s face when I entered the room made the trip worth every single penny. I’m actually tearing up as I type this….it was that powerful. Grandparents provide such amazing wisdom and Adam and I loved just sitting with them and hearing their stories for a few days. I love them so much.

Below are some more photos from our trip and at the bottom of the page you can find all the information about where we stayed and where we ate! I highly (!!) recommend staying at The Iron Horse when in Milwaukee. Adam and I decided it would be our Christmas present to each other to stay there (we never really do gifts since we love to travel so much) and it was such an amazing treat. From the moment we checked in (they give you free cocktails at the door!) from the time we checked out this morning, everything was spot on perfect. It was definitely one of the best hotels I’ve ever stayed at—a destination in and of itself!

I was so excited to share Milwaukee with Adam since he’s never been before and we had such a great time! If you go, definitely check out the Milwaukee Public Museum—it’s one of my very favorite places in the entire world.

Where We Ate:

in Chicago–

Gilt Bar Chicago

The Purple Pig



in Milwaukee—

Milwaukee Public Market

Transfer Pizzaria and Cafe

Where We Stayed:

in Chicago—

The Westin on Michigan Ave

in Milwaukee–

The Iron Horse









You Might Also Like

  • Jen
    December 12, 2011 at 12:36 pm

    That is so sweet about your grandpa! What was your favorite meal of the trip?

  • Hilliary @Happily Ever Healthy
    December 12, 2011 at 12:50 pm

    Wonderful pictures from your trip! Looks like you went to some neat places! I am so glad you got to see your grandpa, so special you guys made a trip just to see your grandparents!

  • Bev Weidner
    December 12, 2011 at 12:53 pm

    I love your bangs! I might copy you. Would that weird you out?

  • Becky
    December 12, 2011 at 12:57 pm

    I’ve stayed at the Iron Horse! It’s so awesome! I love the detailing and atmosphere. It’s a great place to stay. Last time I was in Milwaukee I tried to stay there again, but it was booked solid!

  • Sarah
    December 12, 2011 at 12:57 pm

    What a fun getaway! That’s a great Christmas gift, we prefer to “do things” instead of just giving gifts since we’re both bad at surprises, and the memory of going away for a trip or a show always seems to last longer than a present!

  • Bridgette
    December 12, 2011 at 12:59 pm

    My husband and I just got back from Chicago yesterday- we were there for a long weekend. And we also ate at The Purple Pig. What a small world.

    I’ve read your blog for awhile. Not sure if I’ve commented. But hello! πŸ™‚

    Glad you enjoyed Chicago- we did too!

  • Urban Wife
    December 12, 2011 at 1:01 pm

    Looks like a fab time! Grandparents are the greatest – so much wisdom to glean!

    All the pics esp the one where it looks like you’re freezing your face off is getting me super excited for our vacation in 14 DAYS (!!), but who’s counting. πŸ™‚

  • sana
    December 12, 2011 at 1:06 pm

    I am so happy you got to visit your grandpa after he was sick πŸ™‚

  • Amanda
    December 12, 2011 at 1:06 pm

    I know what you mean about seeing your grandpa – I only see my grandparents a few times a year, but it’s always so, so wonderful. I think my grandmother is probably the sweetest person I know. πŸ™‚

  • Katie @ Katie Without Restrictions
    December 12, 2011 at 1:25 pm

    Looks like a fantastic trip! We live about an hour from Milwaukee so we make it down there pretty often ~ love Alterra, and the whole lakefront! The Iron Horse is definitely on my list of places to stay too. We try to get to Chicago once or twice a year as well, we completely love it there!

  • Caitlin @ Cake with Love
    December 12, 2011 at 1:25 pm

    When I found out the ny grandfather was diagnosed with cancer, me and my husbad bpught the plane tickets and in one week we went from NY to Eastern Europe to see him! it was a surprise πŸ™‚ I will never forget the look on his face as well, and the joy in his eyes after that! I love my granparents & parents tremendously and I fully connect and understand your feelings! God bless them for loving us and for making us better people, and for always being there when we need them!

  • Lindsey (One Sweet World)
    December 12, 2011 at 1:30 pm

    I love Feast in Chicago! Great choice. We are going to Montreal this weekend for a little pre-Christmas getaway – so fun.

  • Jenny
    December 12, 2011 at 1:30 pm

    Gosh I cannot believe that Chicago is so friggin cold already!! how do people do it there..yeesh. Looks like such a fun trip! One of the best restaurants out there Mercat a la Planxa from Jose Garces. Delicious tapas!

    • Kelly
      December 12, 2011 at 9:17 pm

      Actually, this is nothing. It gets much, much worse. Though I will say, having also lived on the East Coast for 8 years I think once it dips below freezing cold is cold wherever you are. Winters in Boston could get pretty nasty as well.

      Though I will say my friends and I always joke that the weather is a pretty good filter in Chicago as it seems to mean that the kind of people who live here are passionate about the city and love, love, love living here. That and minus the obvious lack of seafood, the food here is incredibly underrated.

  • Amy@ahealthyandhappyheart
    December 12, 2011 at 1:40 pm

    What a nice trip…enjoy that special bond with your grandparents…I never got to experience that with my own..but my husband has been kind enough to share his grandparents with me πŸ™‚

  • Cate Hartnett
    December 12, 2011 at 1:42 pm

    Is that a Whole Foods in the first photo? That location may or may not be my favorite place to visit. Ever. I’m glad you could visit with your grandpa.

  • Michelle
    December 12, 2011 at 1:46 pm

    Gahh! I just loved these pictures! I’m a senior at school in Milwaukee, and I LIVE at Alterra. And Transfer opened up another location called VIA on the Eastside, which is conveniently only two blocks from my apartment. The roomie and I tend to frequent it a little too much. πŸ™‚ But their pizza, and a beer, and live music…you just can’t go wrong! So glad you enjoyed your stay in the Midwest!

    • Megan
      December 12, 2011 at 2:24 pm

      Via is my favorite! I live in Riverwest and go there at least once a month. The Paisano (Transfer Special) is sooo delicious!

      • Michelle
        December 12, 2011 at 3:36 pm

        No way! I’m a big fan of their Prosciutto Fungi pizza!

  • MyThy as in "Mighty"
    December 12, 2011 at 2:01 pm

    Never been to Milwaukee but love, Love, LOve, LOVE CHICAGO! Next place I’d live if I ever moved again!

    Its been following you on Instagram and seeing your eats and travels. =)

    • Laura @ Backstage Balance
      December 13, 2011 at 7:40 am

      I’ve lived in Milwaukee for my entire life and it’s a huge compliment for you to say that! πŸ™‚ please do move here!

  • Cait's Plate
    December 12, 2011 at 2:03 pm

    Looks like so much fun! The midwest is definitely a place that I need to spend more time!

  • Heather
    December 12, 2011 at 2:12 pm

    Saw Bon Iver with Fleet Foxes in September, amazing show!

  • kathleen @ the daily crumb
    December 12, 2011 at 2:20 pm

    so fun! feast and purple pig are two of my chicago faves. glad you had a good trip and that you were able to squeeze in a visit with your grandpa… you’re right, they are so important and too often we take their time with us for granted.

  • Rebecca @ Naturally Healthy and Gorgeous
    December 12, 2011 at 2:27 pm

    What wonderful pics! Makes me want to visit!

  • libby
    December 12, 2011 at 2:29 pm

    i was at bon iver on friday night!!! It was AWESOME!! also, love the purple pig!! A guy I went to high school with is the owner/chef!!

  • Liz @ Tip Top Shape
    December 12, 2011 at 2:33 pm

    You were literally across from my apartment for half your trip in Chicago! lol Love Feast. One of my favorite places to go. I went there with my mom once and we ordered the steamed mussels. We had a bunch left so we asked them to wrap them. The waiter ended up dropping them accidentally and had the chef whip up a whole new batch for us. Best leftovers ever. lol

  • katie @KatieDid
    December 12, 2011 at 2:56 pm

    SOO incredible to see Bon Iver, I would die to go to that concert, love all his music so much. It sounds like you had an amazing trip and I’m sure your grandparents were so so happy to see you!

  • Averie @ Love Veggies and Yoga
    December 12, 2011 at 3:21 pm

    Awww, love the post. Being that I grew up in Mpls, then moved to Chicago, and spent TONS of time growing up in the great state of Wisc, I can relate to this post, so much.

    Glad you were able to see your grandparents and that you stayed warm in your coat (adorable!!)

    Great hotel, Bon Iver, Michigan Ave (I hope you shopped, big time!!), grandparents, sharing it all with Adam…fabulous.

  • Jen
    December 12, 2011 at 3:55 pm

    The pizza looks amazing. I think it is great treating yourself to travel and accomidations > stuff and things. An example to live by!

  • Joelle (On A Pink Typewriter)
    December 12, 2011 at 3:56 pm

    Aw, that’s wonderful that you got to share your grandparents w Adam.. I’m planning ot take a trip to Chicago as well this spring so that my bf can meet my grandpa.. I know exactly what you mean about seeing your grandpa- makes me miss mine more!

  • Jane @ In the Pink and Green
    December 12, 2011 at 5:46 pm

    This post is one of the reasons that I love your blog, the paragraph about going to see your grandparents actually made ME tear up because it made think about how excited I am to go home to Michigan (my husband and I live in Boulder, CO) over the holidays and see my own grandparents! Seriously, grandparents are such a blessing πŸ™‚ Glad you had a nice trip!

  • Maria
    December 12, 2011 at 6:05 pm

    Oh I LOVE when I see bloggers visit Milwaukee & Chicago πŸ™‚ I grew up in Milwaukee but I live in Chicago. Milwaukee Public Market is one of my favorite places. Glad you enjoyed your time with your grandparents.

  • Jenny
    December 12, 2011 at 6:07 pm

    I was at Bon Iver at UIC too! Small world:)

  • R. Chandra
    December 12, 2011 at 6:50 pm

    oh pizzzzzaaaaaa that pizza looks amazing. also love the pic of you in your coat – cute !!

  • Lisa @ Fit in the Midwest
    December 12, 2011 at 6:54 pm

    Glad you enjoyed my hometown (Milwaukee) and gave it some attention since it doesn’t get nearly as much as Chicago does. I’ll have to recommend the Iron Horse to visitors to the city.

  • Joey
    December 12, 2011 at 6:55 pm

    I love this post – I feel the same way about my grandparents. I’m so happy you were able to be there with them!!!

  • Lindsay @ Pinch of Yum
    December 12, 2011 at 6:59 pm

    Midwest rocks (I’m a MN girl) and grandparents rock. My grandpa passed away a few months ago and I love remembering those little moments we had with him. It’s a precious gift to be able to spend time with them! πŸ™‚

  • kyla
    December 12, 2011 at 7:18 pm

    Mmmm Francesca’s is one of my favorite restaurants.

  • Liz @ iheartvegetables
    December 12, 2011 at 8:01 pm

    YAY for the midwest! I’m from Ohio but I live in VA now πŸ™‚

  • Kay
    December 12, 2011 at 8:16 pm

    What an exciting trip! And I am SURE that your grandparents just loved your Adam! πŸ™‚

  • amy walters, aDESIGNdock
    December 12, 2011 at 8:17 pm

    Aah….what a fabulous trip Jenna! Love the pics.

  • Shari @ The Daily Dish
    December 12, 2011 at 8:37 pm

    Sounds like an awesome trip. I live in Chicago (just moved here about a year and a half ago) and definitely need to venture to Milwaukee one of these days. I always hear such wonderful things. Glad you got to spend some quality time with your grandpa. There is nothing like it.

  • Laura @ She Eats Well
    December 12, 2011 at 9:00 pm

    Love Chicago, especially. LOVE Bon Iver. I saw him at the Greek Theatre in Berkeley a few months ago. I hope you enjoyed the show, I thought his entire band (like, 9 people!) was amazing live.

  • Laura @ Backstage Balance
    December 12, 2011 at 9:21 pm

    Jenna, I live in Milwaukee and am glad that you had a good visit here last weekend. The Iron Horse is wonderful, and it was a handy spot for me to stop and fill up my water bottle while training for the Milwaukee Lakefront Marathon this summer! There’s a lovely trail that runs from there through the industrial valley, to Miller Park (our stadium). Transfer and Alterra are great, as is the Public Market. And of course the Streets of Old Milwaukee exhibit at MPM!
    Glad that your grandpa is feeling better, that’s what’s most important.

  • Tasha
    December 12, 2011 at 10:48 pm

    Thanks for sharing your restaurant list! You make the mid-west seem so lovely. I will have to visit someday… but in the summer -10 degrees, yikes!

  • Erin
    December 13, 2011 at 1:38 am

    I grew up in Mequon, WI, and the Milwaukee Public Museum is one of my favorite places, too! My three clearest memories are from the under the sea exhibit with the crazy looking squid, the trex eating the other dinosaur, and old Milwaukee- I used to love walking the streets and looking in the windows! What’s your connection to Milwaukee (besides your grandparents)? I rarely get out there anymore, but if I do, I’ll definitely check out the Iron Horse, looks awesome. What a fun trip (I currently live in Southern China so I get weirdly nostalgic for the bitter cold, but you can probably refresh my memory that it does have its downsides)!

  • Heather Michelle @ A Sweet Simple Life
    December 13, 2011 at 4:18 am

    That coat looks so cozy and it looks like you guys had a fab weekend. And it doesn’t get much better than a big slice of Chicago pizza!

  • rebecca
    December 13, 2011 at 5:02 am

    Ha! My husband and I were going to Francesca’s this weekend but cancelled because our daughter got sick. Really want to go to Purple Pig – hope you enjoyed it! And Bon Iver is perfect Midwest winter music – aren’t they from Wisconsin? Glad you enjoyed your trip and got to see your grandparents.

    • Laura @ Backstage Balance
      December 13, 2011 at 7:37 am

      Yes – Bon Iver (aka Justin Vernon) is from Eau Claire, Wisconsin!

  • Molly @ RDexposed
    December 13, 2011 at 5:10 am

    I love that YOU loved the Midwest! Chicago is so great! It’s hard to explain Chicago to someone who’s never been there.
    And I have to admit that I’m laughing at the “cold” pictures and comments because I was just saying how this has been a warm winter so far.

  • Dana
    December 13, 2011 at 5:55 am

    I love the Milwaukee Public Market!!!!

  • Julie
    December 13, 2011 at 6:16 am

    Which dinner was your favorite in Chicago? I’m heading there Friday with my husband and we wanted to try somewhere new for our annual trip/date night!! I’ve heard of the Gilt Bar before, but want your opinion!

    • jenna
      December 13, 2011 at 6:18 am

      Go to Gilt Bar! It’s on West Kenzie street and the ricotta gnocchi with butternut squash will BLOW YOUR MIND. Seriously. Just go.

  • Charise
    December 13, 2011 at 7:48 am

    Yay! So glad you had a good time in Chicago (my homeland ;)). Nice restaurant picks, and the hotel in Milwaukee looks amazing.

  • Kelsey
    December 13, 2011 at 8:58 am

    Glad you enjoyed Chicago! You came when it’s super cold, but it looks like you had a good time!

  • Rachel @ I'm Loving Today
    December 13, 2011 at 9:45 am

    I’m glad you had a great time in the Midwest… specifically in my adopted hometown of Milwaukee! I truly think the city is completely overlooked for its cool vibe, great culture and, of course, amazing food. I hope you enjoyed your stay here! The Iron Horse Hotel is incredibly cool and Alterra Coffee is the best java around πŸ™‚

  • Milwaukee Public Market
    December 13, 2011 at 9:51 am

    Thanks for visiting the Public Market, Jenna. πŸ™‚ We hope you enjoyed Milwaukee. Come back soon!!

    Milwaukee Public Market

  • Jill in Chicago
    December 13, 2011 at 9:53 am

    So I live in Chicago and I’ve never heard of Gilt Bar — I’m curious how you found it? I went to their website but the sounds are super annoying and the link to their menu seems to be broken. They certainly aren’t enticing me to go there.

    • jenna
      December 13, 2011 at 9:59 am

      Yelp! It was wonderful.

    • Lauren
      December 13, 2011 at 1:09 pm

      I’m a huge fan of Gilt Bar! It’s in my neighborhood which makes it convenient but worth the trip from anywhere in Chi. The beef pot roast is ridiculously good! You should check it out, Jill.

  • Laura
    December 13, 2011 at 10:43 am

    So exited you made it to the purple pig!

  • Amy
    December 13, 2011 at 5:02 pm

    Gilt bar is SOOO good!! hope you liked it!

  • Brittney @ Brittney Breathing
    December 14, 2011 at 4:53 pm

    We almost decided to have our reception at the Iron Horse! Way too expensive though…but I love that they immediately give you a drink!

  • christmas tree rolls β€” Eat, Live, Run
    December 15, 2011 at 3:09 am

    […] when I was visiting my grandparents last week my grandma and I got to talking about Christmas cookies…her favorite recipes and the recipes […]

  • diana@mymarblerye
    December 15, 2011 at 5:21 am

    so….where are the food pics?!?!

  • Alison
    January 6, 2012 at 1:56 am

    Shoot, I live in Milwaukee but now I want to stay at the Iron Horse! It’s nice to hear some love for our fair city, which often doesn’t get the attention it deserves.