windy city.

Renee - looks so so fun! i grew up in a near suburb of chicago, and i just love that city!! we’ve lived in Nebraska and are now in Boston (both places we really like), but Chicago has such a special place in my heart. i love the spot where you took those skyline pictures. another good (farther away) view is from Promontory Point in hyde park, a few miles south of downtown. I love the view from the hancock gal’s bathroom on the 96th-ish floor. Fave pizza – pizanos & giordanos. and Portillos – oh my word, I miss this. People don’t even know what Italian Beef is outside of Chicago. [this was shocking to me! haha] i so so miss it & ALWAYS eat pizza and portillos when we’re back to visit. we like shopping on state street (hello discount stores!)
Next time you’re back, venture to the Pilsen neighborhood for Mexican food and go on a mural tour. It’s my FAVORITE thing to take visitors to there. So different from anything else you’ll experience in that city.

Amy M. - The last time we were in Chicago we went to the Money Museum and it was fascinating. Granted, we were with a school tour and the guide for it had super dry humor. He was great and had amazing stories. Our favorite place to vacation is Bald Head Island, NC. You take a ferry over and then there are no cars. I would love to see it through your eyes. Lots of adventures and you feel like life has really slowed down. It is very family oriented, which is one of our favorite things about it!

Eugenia - Chicago is definitely on our bucket list. San Francisco is my favorite city. Small enough to walk with a little something for everyone. Cable cars, sour dough, Golden Gate, Alcatraz, Chinatown. Also, love Vancouver, BC super clean and there is Victoria island. I’m a huge fan of public transit, Vancouver has everything including a ferry.

xxooo

Jenn - The Mr. and I got engaged in Chicago (on Lakeshore Drive in a horse-drawn carriage). It is our FAVORITE city to visit (we used to live close, now we don’t). But, we still go back to visit annually. Our family tradition is to take the kids (4 of them) to Chicago sometime during the Christmas holiday season. We eat at the Walnut Room and visit with Santa. It is the best weekend of the year for the Mr. & I (and for the kids)!

eric andrews - I used to live near Chicago. Loved Pizzeria Uno! Yummm!

Angie P - I’m from Chicago (my dad lived on the southside near Midway until I was 12) and my family still lives there! We visit my dad every year and try to do something fun with the kids – this year it was Navy Pier (ugh. the ferris wheel kills me.) and lunch at Ed Debevics. I miss living there – my husband actually ordered Portillos for my birthday a few years ago and had it shipped to us in Georgia! (It was expensive…but delicious…and so thoughtful!)

Maria - How fun! We did a weekend escape to New York minus the boys for my 40th earlier this year and it was so much fun! We also love going into New Orleans whenever possible for the day (we are really close). Any big city is on my to do list…would especially love to go back to San Francisco.

colleen from Alabama - My hubby and I went there for our 15th anniversary last year. They had a “broadway in the park” preview at the amphitheater by the bean. It was hands down our favorite thing. It was free and they had probably 20 acts from the Broadway Shows that were touring and stopping in Chicago during the next season. FABULOUS! It was beautiful weather (august) and the performances were so good. We also loved garret’s popcorn. My kids want to go back with us just to get that!

Jen - Chicago is MY FAVORITE!! We lived in western Michigan for ten years and visited often and I just love Chicago. I tell my husband that I want to retire in a loft apartment in Chicago! (I love the cold and snow too though, so I’m weird! :-))

And the Portillos chopped salad is TO. DIE. FOR! I’m not a huge milkshake fan so I don’t get those either but oh the chopped salad!

Glad you enjoyed it! I know you’re far away but Philadelphia is also a cool city–rich with history and LOTS of fun things to do in the surrounding area (Valley Forge, Amish Country, DC, etc!)

Barbara - We just moved from Chicago to San Diego— I miss my city! Cloudgate is indeed awesome, I like to refer to it as the Monument to Selfies lol
Looks like a fun visit! Willis Tower just sounds stupid, it will always be Sears Tower to me hahaha
I definitely miss chicago, but I will not miss the cold weather that’s headed that way soon 😉

Valerie @ chateau a la mode - Hi Megan, aren’t trips auch great family memories. Chicago looks like it was super fun, it’s still on my lit of places to get to. Our best trips have included my husband’s sister and her family (they have 6 kids). We are in LA and they are in San Francisco. We have done New York city, Washington DC and motorhomes to Yellowstone with them. I recommend all of those as my kids have such great memories associated with those trips. Maybe only because kids waaay outnumbered adult supervision 😉 but great memories none the less.

Jaimie - Great pics!! Love Portillo’s!!

Lucky enough to have had one sibling live in San Francisco and another in New York City…and prior to that, Boston. Made for very inexpensive trips as was able to crash at their places and had built-in tour guides from a local’s perspective. Would recommend all three of those fabulous cities.

We’re in suburban Chicago, so in addition to what the city and suburbs have to offer, we really enjoy driving up to Lake Geneva, WI for a quick little get away.

One of the times I was visiting my sister in NYC, she mentioned that she hadn’t really enjoyed the city as much as when my Mom and I were there to share in all of the wonderful things the city had to offer. Another confirmation that it’s not necessarily where you’re at but who you’re with. Based on your blog posts and amazing pictures, it looks like your family could have a blast where ever you’re at as long as you’re together.

Thanks for sharing your thoughts and photos…they’re a constant inspiration!

Stacy P. - We loved Boston with our 3 kids (13, 10, 6). We toured around, then rented a car to drive to Newport, RI to see the amazing houses on the coast (The Breakers, Marble house, etc) then we drove up to Maine. Beauitful. We did the RI/Maine thing in a day–visited the beach at Ogunquit, Maine. Very different from the beaches we are used to in Florida! Really great, though. It was mid-July and the temps there were in the 70s…waaay too cold for us Southerners, but the “natives” loved it! We played in the sand with our jeans and sweatshirts on while the locals jumped in the waves. The whole New England coast is a must see.

Jen Sully - I love Chicago! I’d have to say my favorite thing there is Garrett’s popcorn!!! The best.popcorn. EVER!! 😉

Marla - I moved from southern Wisconsin to Montana but my parents are still an hour and a half away from Chicago. For a while I would meet my college friend there each Christmas. I loved the big city for a day. I met a lady in a coffee shop who couldn’t imagine living in Montana. She thought I climbed mountains to get to the store.

Christy - OK, I never comment but I just had to say that I have been reading your blog for years and it just dawned on me that we were at that fountain thing on the same exact day. We were in Chicago for my brothers wedding — if you remember seeing a very harried woman with a 4 year old, 2 year old and 6 week old baby.. that was me!! Ha! Ha! What a small world we live in. I have to wonder what I would have done if I had seen you. That would have been surreal.

Tanya - I looooove Boston…and Cape Cod. We did that trip numerous times as teenagers with my fam. It was one of the first trips I took when I was newly married and I’ve done it as a grown up with just my sister’s as well. Great sights, great food, great history and great shopping 🙂

KirstenP - Our family lived in Chicago for several years. We all love to go back for a visit. I’ll admit the Sky Deck scares me and I haven’t even been there, but I will go on it some day soon. BTW, the Bean was actually named Cloud Gate, but I don’t think many call it that. I love the energy of Chicago and it’s people and visitors and that it’s right next to Lake Michigan. Thanks for sharing your photos and memories!

Kassondra Taylor - i went to chicago twice. the first time was with my 8th grade class and we went to a 50’s style diner that had one of the first photobooth! Then I went back for a girls weekend with my mom,grandma and aunt. It was really fun but we could not find that diner! would love to know the name of it or even if it’s still there!

Jen - I love Chicago! I’ve only been there a few times, though, and not in over 15 years. Need to take my kids there. So far my favorite city to visit is Savannah, GA. We’ve only been there once, but we go to Hilton Head, SC every summer and Savannah is only 45 minutes from there. I hope to make more trips there in the near future – it is so beautiful!

Laura - I went to Chicago for my anniversary for, like, three minutes…had to get a flight back home to avoid hurricane Sandy…BUT…I loved the bean, and all the cute bakeries, but mostly just enjoyed WALKING and people watching and beautiful shops. I am a city girl at heart…which is why, the ONLY city you need to vacation at is NYC…but with ME…I will give you the non tourist version of NYC and you will love it xo

Nanette - Your photos have inspired me! We live in Highland Park and I have never done the tower…my 3 boys would love it! It is now on the list! There is a German restaurant near the bean that my father in law used to go to as a boy…Berghoff’s. Everything in the bar is still the same – he used to get a sandwich for a quarter. Very good if you like German food and the kids love their root beer!
You might like the Museum of Science and Industry…lots of neat, historic things for kids.
Awesome summer!