Well…guess what? I am posting more pictures of Chicago than any one person probably cares to see. Chris and I had an amazing time – thanks to so many great tips from friends and blog readers. We joked that we were doing the “Chicago By the Blog” tour…also known as “Chris and Ashley’s Walking Food Tour.” A few people recommended doing a segway tour, but once we got there we realized so much of what we wanted to explore in Chicago…tours don’t really go to those places. We spent just a bit of time downtown. There was so much we missed downtown, but maybe we’ll go back one day.
With four kids we don’t do much walking/exploring on vacations. So, we decided that would be the route we went. We took many of your suggestions for neighborhoods and restaurants. We only used public transportation – which considering how all over the place we were, it was such a great decision. Basically, we rode the L somewhere and then ate, walked about 2-3 miles and ate again..then repeat all day. I’m guessing we walked a minimum of 10 miles a day – which was awesome considering the amount of food we consumed in 4 days!
These are the main areas we hit:
Devon St.
Bucktown
Wicker Park
Lincoln Park
Magnificent Mile
Millenium Park
Chinatown
Bridgeport
University Village/Little Italy
Gino’s East vs. Giordano’s – that was the big debate in the comment section when I asked recommendations. They were both AMAZING. However, Giordano’s got our vote. The suggestion to get the Chicago Mix from Garrett’s almost got nixed when I realized what that mix was. I trusted you guys and you did not disappoint. It was crazy good.
My favorite part of the L was the diversity. The other passengers always reflected what area of town we were in. The majority of the time Chris was the only person on board that looked like me – it was beautiful. So many cultures each with their own niche in the city. It felt like we got to travel the globe in four days…and experience the food!
We walked Devon St. and stopped at a little bakery. I did not recognize anything, so we just asked the woman working to pick something for us. These reminded me of a doughnut covered in caramel syrup. One of the many things I love about Chris, is that his adventurous spirit doesn’t stop with physical adventures. He is always up for trying something new with me.
A trip to Bucktown and Wicker Park…with a visit to the Renegade Handmade shop. I can’t believe I was there one week before the craft fair. Bummer.
I struggled taking pictures in Chicago because four cute kids weren’t included. Once I got home, I noticed how drawn I was to the lines of the city. I don’t typically take abstract pictures, but I guess something about Chicago brought out a different side of me.
Hot Doug’s. 45 minute wait. Never seen a hot dog menu with ingredients I can’t pronounce. It was worth the wait.
Thank you for the Paper Source suggestion. I spent more money than I should have…Chris did too.
Bridgeport Coffee House…breakfast sandwich and an Arnold Palmer (it was too early for another cup of coffee!)
Best egg drop soup I’ve had in a long time. I don’t remember what the meat dish was, but it was d.e.l.i.c.i.o.u.s….
A trip to Little Italy for tiramisu…remember we were walking several miles between all this food!
The Hancock Tower…from the top and from below.
The only real touristy thing we did was an Architectural Tour on the river. It was so much fun and a great way to see the beauty of downtown..and its history.
The week before we left I was wrestling with whether or not to take my camera. All the images above are with my Canon 5D 24-70mm lens. That is a heavy, bulky combo. I have a backpack for it, but I didn’t want to use it. It kind of flashes “Hey I’ve got a great camera in here”…not the wisest thing to do. I was debating between using my 5D and using the Hipstamatic app for iPhone. The reality is I will not be framing these pictures anywhere in my house. I have limited wall space and I am partial to using it to display family pictures. So with that in mind I thought it would be fun to make a square photo book full of iPhone pics. Lots of people told me I was crazy…a photographer not taking my camera to Chicago. I took it.
I wish I hadn’t. It is a personal preference. These pictures will rest here on this blog and I’ll use them in a book….but I would have loved the feel of an entire Hipstamatic book. All that walking with a heavy camera on my shoulder, I was jealous of Chris’ iPhone!
If you are planning a trip to Chicago, I recommend reading the comment section of this old post!
*update…I removed a portion of this post about my first visit to the American Girl Place. My joking about a personal experience was not worth hurting the feelings of others.
by AshleyAnn
show hide 67 comments
Sara - That last photo is my favorite. Really nice. Glad you had a great trip!
Jenny - Your last photo is taken at my most favorite spot in the whole city. Happy to see you even found that; you had an amazing trip. So glad my town treated you well!
Liz - I LOVE the last picture! How did you guys do that with an iPhone? Beautiful!
giozi - Gorgeous trip. Before see your pictures I would like to know Chicago too.
Ashley your next stop must to be Peru, Chris must to eat the peruvian food.
Celia - Wow!! So awesome. Selfishly… I’m glad you took your camera! I loved seeing your photos.
Glad you guys had a great time and thanks for sharing with us!
Amy - Chicago is one of my favorite cities! I loved seeing it through your eyes/camera lens!
Debbie C - Your pics are beautiful! They remind me of the wonderful things about this city that I’ve forgotten (from living in the burbs for so long). Sounds like you hit a lot of great spots in Chicago!
luvsclassics - Hello and good morning. I spotted your post on Chicago by the Blog from Ms May Days. Looks like bringing your camera along was well worth it; your photos captures the variety of the “Windy City”. I like the blue skies against Chicago’s skyline and also all of the food images.
We just visited Chicago very briefly returning from vacation in the Lake Geneva, Wisconsin area. We, too tasted the Chicago style pizza at Giordano’s but in the Oak Park section. We plan to visit again, and I’ll be sure to bookmark your post and the comment section. My link for Skywatch Friday, has our Chicago memories.
kassondra - THAT PICTURE AT THE END DOES DESERVE TO BE HUNG ON THE WALL IN YOUR BEDROOM THOUGH!!! this inspires me to plan a mommy daddy only weekend vacation
Leila Marie Lawler - Oh, I am so glad you said that about the American Girl place!!
Your photos are gorgeous, although I sympathize about lugging the camera. Either way — great post! As a mom of 7 I can totally relate to the fun of just GOING and EATING!!
Sarah Karlsen - Actually, American Girl does sell a baby doll, it’s called Bitty baby. She is quite cute with lots of clothes and equipment available for her. Also, comes in many ethnicities.
amanda torres - You are so right about Chicago’s diversity. Thatt’s what I love the most. The L is exactly how you described it. Loved all you pics, but the only one missing is the Puerto Rican district!
laurelbud - Amazing photos as ever!
So pleased I read this post AFTER I had lunch otherwise I would be ravenous after drooling over your foodie pics.
LB
Erica - Great pics of Chi town! The same thing happened to me when I went to the American Girl store…but I had a better employee help me so I could only buy one of the bitty baby twins.
Michelle D. - I went to Jamaica last month and I wrestled with the same decision- to take or not to take my camera. I have a Canon t2i. After much deliberating I chose to take a Nikon point and shoot and was happy with that decision. No bulky camera to haul around doing activities!
Erica - I’m glad you took your camera because I’m enjoying your photos
But I can totally relate… that is always the debate here too. I get tired of the heavy camera on my back/shoulder and usually end up taking the 24-70 as it is the most versatile… but so heavy!
Lacey - Before you take another trip like this, you should check out the Rapid Straps! They totally make carrying a heavy camera/lens combo no big deal.
Great photos… and thanks for the tour of Chicago!
Kim - Beautiful pictures!! But the last one is the BEST!! Glad you had a great trip and thanks for sharing it with us!!
Fee - I’ve been to Chicago in June and I loved it. I think it’s even more interesting when you are fro outside the US
! I’m splitting my pictures into several posts on my blog. here are the ones I’ve done yet: http://feeistmeinname.blogspot.com/search/label/Chicago – I loved looking at your pictures. It was a bit like going back 
!
Hannah B - Looks like an awesome trip! I told my hubby that I really want to go to Chicago. He’s already been and our goal has been to travel to *new* places together. So maybe I’ll do a girls trip sometime.
Christina - After reading this, I want to go to Chicago. And Eat. Wow! Love the last pic! That was taken with your camera, right?!
the whyte house - paper source…sigh. everytime we visit my husband’s family in st joe, mo, i tell him i want to take the 40 min drive into kc and go to paper source…and we never do. lol. i think i’m afraid of the city and parallel parking. hahaha! i blame my driver’s ed teacher at the i-high for that.
i’m shocked that you’ve never been to an american girl store. we went to one in dallas 2 yrs ago. $100 for a doll? um, i’ll just go to the disney store, thankyouverymuch. 
Rebekah - How do you make your photo collages or set them side-by-side like that?
KaraM - I LOVE all the lines! beautiful!
Susan - Beautiful pictures, my favorite is the last one of you two.
Life yourself I’m getting ready to hit the road for three weeks, back east and then the Carribean. I’m not sure wether to take a point and shoot camera or my 5DMarkII with a heavy lens. Decisons – Decisions – Decisons
Carrie - I live in Chicago, and it’s always fun to see this great city through another’s eyes! Glad you enjoyed your time here, come back again. (and I completely agree with your feelings about American Girl!)
cailan - You two are so stinkin’ cute! So glad you had a lovely time – I would have struggled with the camera decision too, but your pictures are superb.
lauren - that last picture is SO FUN!! chicago is the best!!
Shauna - Great, now Im starving. And all I want is one of those hot dogs!
Krystina - Oh man! Now I want to go back to Chicago! After I swore off it’s traffic and everything! LOL This time I’ll just have to not drive. Maybe take the L or a taxi or something.
Jamie - Wow- looks like you had a great time.
I struggle with the ‘should I take my camera, should I not’ quite often. I have the Canon 7D, so it is heavy. However, I just took your online Snapshops course that was AMAZING- so at the moment I want to take it everywhere and use my manual mode!!
I am asking for a small point and shoot for Christmas though. One that I can always keep in my purse. Anyone want to recommend a small/lightweight point and shoot they are in love with??
Chicago Food Planet Tours - Awesome pics! It looks like you captured the essence of the city in your trip. If and when you come back to Chicago, give use a holla! We’d love for you guys to join us on one of our food tours. — Ismael, Community Manager, @ChiFoodPlanet
Kristen - I’m so glad Chicago showed you a good time!! Sounds like you definitely experienced the best of the city!
Karen - Just wanted to let you know that American Girl does sell a baby doll. Also, while their prices are a bit high, they offer quality products that are not only diverse but historically accurate, as well.
Laura - looks like so much fun w/ your hubby. enjoyed reading:).
bopha - That is my kind of vacation, I am such a foodie, I plan our trips around where we are going to eat. Ryan comes along but doesn’t get quite as into it as I do. I love the last picture, great reminder photo of your trip.
Lisa Pummel - Now I want a hot dog.
Kate @ Songs Kate Sang - Oh, fun! Have you heard that song ‘I Dream of chicago’ by the Parlours? (I think that’s the right name). It’s awesome!
natalie - Indian sweet= gulab jamun http://en.wikipedia.org/wiki/Gulab_jamun
Miranda - Looks like you guys have an awesome time! I CANT wait to visit Chicago!! That is def on my MUST SEE LIST soon!!!
jessica - yay! my hubby and I just moved from MS to about 30 miles outside Chicago and are having a blast riding the train into the city on the weekends. Thanks for all the great tips! Now we’ll know where to go!
Jill E. - American Girl is a wonderful store for little girls who NEED to be little girls and not wannabe teenagers. The dolls and their books inspire imagination and magical play. And their library of books is incredible… you should check it out to see all the amazing topics they cover for little girls. The “Look like Me” dolls are excellent…. the first doll my little one ever got was crucial for her since she has mixed ethnicities. It was an amazing bond. Something you may want to check out if your adopted child is a little girl. Bottom line is that little girls need to be encouraged to be little girls and AG does a remarkable job with this.
Kristine - We live in Chicago, and I loved seeing so many familiar places! (And some new ones!) So glad you had a wonderful time!!
Katie - The last picture took my breath away! In fifty years that will be one your kids will cherish!
Mindy - i am so happy you guys got to go on a getaway and chicago isn’t THAT far.
next time try blue man group. it’s a fun, loud, colorful show.
i love the last picture most. it is very cinematic.
Shara Leman - Glad to see you made it to PaperSource – that place is simply fabulous!
I should have been on the ball and suggested some places before you got back from your trip but Pizano’s has the best pizza that I’ve ever had anywhere. Not a deep dish experience but so much better…crunchy cornmeal crust, fresh tasting marinara. It just can’t be topped.
Maybe next time, eh?
Glad you had a great trip. Chicago is a cool town.
Patricia - What a great trip! I have a Paper Source 2 miles from my house at a gorgeous outdoor mall. I seriously have to stay away from that side of the mall. Don’t even park near it;-) It’s such a great place for anything fun and creative!!
Jennifer D. - Your photos are gorgeous and your storytelling is so real! I adore them both! It looks like you guys had a wonderful trip. It makes me want to take a trip to Chicago too!
Betsy - So fun to read this post! I used to live outside of Chicago, so I’ve been to and love many of the places you visited & photographed — Devon St., Renegrade Craft Fair/Shop, Chinatown, Paper Source, architectural tour, downtown touristy stuff, etc. Thanks for the walk down memory lane!
lauren - We went to Chicago for my 30th birthday this past May and had the best time! Your post makes me miss it SO MUCH.
Morgan - Thanks for sharing your adventures in Chicago! I really enjoy your blog. It always inspires me in many creative ways. I grew up with American Girls dolls (and a bitty baby) and I love them, but I thought your interpretations was SO funny and real. I grew up in a house full of girls, so I really enjoy reading about and seeing pictures of your life with boys! And, your little girl is lucky to have all those brothers. I always thought I would want a house full of girls (like I am used to), but you are changing my mind…that lego store looked pretty cool, too!
Thanks for always keeping it real.
able mabel - Loved the pictures of Chicago. Thanks for taking your camera along so we could enjoy them.
(p.s. bum deal I missed the American Girl Doll picture. While I think the idea behind American Doll is wonderful, I think it’s way overpriced and will not buy the dolls for my girls. I will buy the books but not the dolls. They’d just end up on the floor anyway. My girls are not doll players.)
Tenille - So glad you got to experience Chicago! It’s my city (or at least thats how I feel). Love just walking around the neighborhoods. Always feeling like I discover something new. Love all your pictures!
ashley jensen - How fun to get away with the husband for a few days!! I know the kiddos are missed but it’s something you have to do!! I would totally wait 45 minutes for a hot dog too!
Kirra Sue - Ya! Pretty pictures Ashley! Loved them all. Glad you had fun!
racheldenbow - WOW! This is getting me so excited! I wish your trip could’ve been this weekend, too, because I’ll be going to Renegade with Red Velvet. First time on both counts for me and I hadn’t really given it a lot of attention yet because of regular life at home but with all of these photos I’m getting pretty jumpy in my seat about all of that visual stimulation! This and too much coffee is going to have me twitching all day.
tanya - as always, thanks for sharing. love the abstract and hipstamatic shots – super creative. i’ve heard it’s not the camera that makes the photographer, it’s the person behind it that’s the artist.
Kristen Duke Photography - I feel the SAME way about my “big camera” vs. my “little camera.” When my children are involved, I was great images and its worth the sacrifice of lugging ole biggie around. Hubby and I took a trip to France a few years ago and we were backpacking. I decided to leave my 5D home, but it was really sad for me not to have it…but maybe I was enjoying the experience more instead of worrying about where/how to get the best shots. It’s a tough call. Love that last shot (that couldn’t have been with an iphone…and seems worth it for that) and I’m bummed I missed the Americal Girl controversial comment…;)
Lindsay - Oh Booo!!! Put the American Girl part back on. Now I’m curious.
Funny the things people get worked up about. My 2 girls are crazy about those dolls. And the stuff they have for them is ridiculous. Very cute, but it’s in-sane how much stuff they have for them. I get overwhelmed just looking at the catalog. I think I’d die if I actually went to a store. Be advised-NEVER take firecracker with you when you go to the store unless you’re prepared to take out a second mortgage on your house.
I’d love to read about the experience. I vote you put it back on!!!
Megan - I missed the American Girl issue but I think I get the gist. I loved american girls when I was little. I get that it seems kind of… ok REALLY ridiculous, all the stuff they have. But for me I was only allowed to get one or two things for my doll on special occasions. They were made for older girls who will take care of the dolls. The creator said a good way to tell if a girl is old enough is if she can read the books. I’m waiting to bust mine back out of storage for my daughter. Either way to each his own (or her own)
Tina - When I went to NYC in Spring of 2010, I did take my 5D and just the 24-70 lens. I did take some lovely photos, but like you and Chris, my favorites were taken with my iPhone and Hipstamatic app. In fact, most of the time I leave the Big Kahuna at home and know I’m covered should a photo moment present itself.
Chicago looks amazing. Now that we’re only a 7-hour drive away, we plan to head there next summer!
Stacey - Ashley, your pictures are beautiful!! And they remind me of memories from when I lived in Chicago. I loved it there and would move back there at the drop of a hat! Looks and sounds like you guys had a great time. Glad you enjoyed your trip and more importantly, your anniversary! And PS, I’m glad you took your camera!
Becky - Do people recognize you when you travel?
Katie - I’m from Chicago so I find it completely boring, but it’s nice to see someone go and not just spend their time entirely downtown.
tara pollard pakosta - I live in the Chicago burbs and cannot believe I have never gone down there on a date. going to do that this year now that my girls are getting older (10 and 11) and I can leave them with my friend finally….beautiful photos!!
my girls are OBSESSED with American Girl DOlls. they make stop motion videos of them, do photo shoots of them set to music and also even made a DOLL MART (like walmart) for them…they get hours of play out of them and they even have learned so many things about the different time periods, so in our home, AG dolls are quite special….But I do NOT like the prices!!!
tara
Stephanie - I LOVE the last photo with you two looking into the city at night! So amazing!!
caru - Like always love your pictures, and I have an Iphone only for the Hipstamatic app. But love you r husband Tshirt, where is it from? My husband love it!!