My parents and I love to travel. We often went on road trips and vacations when I was a kid and we have many special memories from those trips. I feel very lucky that I find joy in traveling and that my mom and I are able to take trips together every couple of years. Back in November we went to Chicago together. It was a great trip – even though we got a little lost initially, my mom had a bad cold, and it was freezing! Those things just make it all the more memorable though.
We stayed at the Hyatt Regency Chicago and it was the perfect location to walk anywhere we wanted to go. And we did a lot of walking! We bundled up in our hats and winter coats each day and we made sure to keep a warm cup of Gingerbread Lattes in our hands at all time.
Here’s a collection of some of my favorite photos from our trip.
There are more photos that I have to get from my mom. Some days, I admit, I was just to cold to take out my camera. So we kind of traded off. She would take pictures and I’d take a break. Or I’d take pictures and she’d take a break. She has some beautiful ones of the Chicago Cultural Center that I would love to share. If you visit Chicago, this is a must see. It’s one of the most beautiful buildings I’ve ever seen. It used to be a library – so it had me the minute I walked in the door.
We had such a fun time, that I can’t wait to do it again. It was a long time between trips for us, our last being Toronto in November, 2008. We like traveling that time of year because it’s fun to see how other places get ready for the holidays and we get to regal our families with stories of how cold we were and how much walking we did in spite of it!
Here’s a photo of Macy’s in Chicago, it was so festive!
I’m looking forward to our next trip together and I’m hoping it will be next year and that 4 years won’t go by again with us saying “we should….”. It’s a great time with many special memories and one that I think we’d both love to see happen much more often.
What about you? What was the last trip you took? Any plans to go anywhere soon?
Rebecca Parsons says
I don’t live that far from Chicago yet I haven’t been to it yet. I would love to visit. My brother has stayed there for business and said he loved his visit.
Robin Wilson says
Who knew? I had no idea that Chicago had so many wonderful things to see and do. I have just never thought of it as a real tourist attraction. My bad ~ it is wonderful.
I love visiting Chicago! Great pictures!
I have always wanted to visit Chicago! thanks for sharing!
Anna H says
Chicago is a beautiful city! <3 Glad you enjoyed your trip!!
Sandy VanHoey says
Great pics and although I’ve never been to Chicago, one day possibly I will. Y’all just have so much fun and I agree, don’t make it 4 years again. Nothing beats a great time with Mom
wow looks like you guys had fun that looks like a great mother daughter time
Cynthia C says
I took a trip with my mom last year to Seattle in January. It was memorable and fun, but I think it’s the last winter trip I will take unless it’s to a tropical location. We froze!
I loved seeing your pics from Chicago! I’m planning to go there at some point in the near future, and the pictures make me all the more excited about the trip! :)
Cathy Linard says
AMAZING PICS! My kids have always wanted to go to Chicago. Thx for the tips!
Kenny F says
sounds like fun!
Ellen B says
I’ve never been to Chicago – looks like there is a lot to do there. This year I need a beach trip since the last time I saw the ocean was 1997!
kelly nicholson says
i really want to see chicago,ive been to NYC,so maybe one day,,,and maybe when its safer
Kristine E. says
Beautiful photos, thank you for sharing :)
Janet W. says
What beautiful pictures and memories you’ve created!
John Hutchens says
Chicago is a busy city thanks for the great review
Dagmara Hawkins says
I would love to go to Chicago one day. thank for a great post
Christopher Sorel says
wish I could find a kids friendly hotel that was reasonable there
Looks nice up in Chi town, but way too cold. I do want to visit it at least once though; aside from the one time I drove through it with my folks on our road trip from Alabama to Wisconsin.
Betty Baez says
My sister came up from texas and we took a day trip to the city (NYC). Chicago’s my hometown, great pictures! I sure do miss living there
Jerry Lafferty says
wish you would have gotten a pic of Wrigley Field. Nice pic of the Tribune though.
I’d love to visit sometime. What a beautiful city! Your photos are awesome! The buildings are simply amazing!
We love to make a stop in Chicago when heading to Wisconsin. There are so many things to see and do.
Heather Hayes Panjon says
Looks Like A Great Trip! So Special To Spend A Trip With Your Mom :)
i love Chicago! love the pictures
Janet W. says
Great pictures! Looks like you created memories you will remember forever.
What a beautiful set of photographs. It makes me actually want to go there, whereas before, not so much! I did notice that the ferris wheel was empty! Musta been cold, cold!
Road trips are the best! I personally enjoy them more than flying, more time to bond with the family. Our last trip was to San Antonio, TX it was our first family trip, my kids were so excited! we are planning on going again on the summer and if everything goes as planned we are taking our kiddos to Walt Disney World on spring break, now that will be interesting, 18 hrs in a van with nine kids….
PS. You took some great pics, Good job!
You are right about the Cultural Center. Beautiful staircase and changing art exhibits. Also on a hot sweltering day it’s a great place to cool off in. Great pics.
BTW – I found your blog on G+.
My most recent trip was a crazy 36 hour trip with a good friend of mine. We drove from Oklahoma City to Kansas City, MO to see a White Sox game and then got up and went to Saint Louis and met Dan Aykroyd at a signing and then drove back for a birthday party for my wife’s best friend. Crazy, fun weekend. I plan on going to Chicago this summer and checking out Second City
Marcia Goss says
I would love to go to Chicago again! When I lived in Indianapolis, we would take the kids and go every summer for a few days. Our favorite thing to do was go to Wrigley Field and watch the Cubs play.
We took our kids to Chicago a couple of years ago and we all had a great time. We went to a few museums, did some shopping and ate some great pizza! We are planning on doing a cruise this year with the entire family, should be a blast.
Katy M says
Wow! What an awesome trip! You’re so lucky to be able to travel with your mom.
I’ve never been to Chicago and have always wanted to go- it’s definitely on my list.
Thanks for the great pics!
Kristin Wheeler (Mama Luvs Books) says
This is one of my favorite cities!!! I used to go there often when I lived in Peoria, IL!! Miss it! Great photos!
Tree Lindsay says
Oh wow.. those are beautiful photos! I haven’t been to Chicago since I was a child, and our plane was grounded on the way to my grandmother’s house during a blizzard. lol I would love to go back and visit though!
Jennifer Clay says
Love your pictures! Looks like you all had a ton of fun.
A couple years ago, my mom, sister & I had a “girls” weekend in Chicago. We had a great time! Love being able to travel with them!
Doug W says
We’ve had unpleasant experiences in other big cities, but I still feel like we should try Chicago or NYC at least once.
How much fun is that? It looks like both of you had a great time despite the freezing and bad cold. I am going to the Krispy Kreme blogger summit next week and I can’t wait although I know it will be cold!
Allyson Bossie says
Gorgeous pictures, and it looks like you had grand time!
Shell Fruscione says
Those are such beautiful shots! I’m a bit homesick now though- I lived there when I was little & I totally recognize most of those places. I’m overdue for a trip back to Chicago!
Amanda Sakovitz says
Love the pics! Looks like you guys had a blast!
Rachel at managedmoms.com says
Love it! I’m super close to my Mom, too…and she lives 2,000 miles away from me :( So great that you two make time together to take such special trips!
great photos! I would love to visit Chicago
Tragic Sandwich says
I love Chicago, although I don’t get there very often or for very long. Our most recent trip (Mr. Sandwich’s first!) was almost four years ago.
The last trip we took was to visit my side of the family for Thanksgiving, and that will probably be our next trip as well. When Baguette is a little older, we want to go visit my brother and sister-in-law in Austin–but our dream trip is to go back to Kauai with Baguette.
Amber Edwards says
Wow, I never thought Chicago could be beautifuL! But you really captured it! It looks like a great place to visit!
Welcome to our cold, windy city! Looks like you guys had a blast. You took some incredible pictures of the waterways. :)
Krystle(Baking Beauty) says
Your photos are beautiful and the architecture is stunning! The last trip I took was to Dewey Beach in Deleware.
Tammy S says
It looks like you two had a great time even though it was cold. I would love to be able to travel with my mom. she just doesn’t like to travel any more.
Thats so great that you travel with your mom. I would love to do that someday
I absolutely love to travel as well! It looks as though you had a fabulous time. The last time I went on a trip was when we headed up to Mammoth Mountain and Yosemite. So beautiful!
Absolutely gorgeous! Your mom could pass for your sister!!
Oh what an experience! I love all of the pictures, looks like this was such a fun time. I would love to take my Mom on a trip some day to help build our bond as mother/daughter that we never really “had” per say. <3
Looks like a great time! I love all your pictures. I’ve been to Chicago a few time, and it’s such a neat city. Everyone is so friendly too!
Wow! You saw a lot! We went to Chicago a couple of years ago but it was the weekend between New Years and Christmas and it was FREEZING! Seriously! Most of my time was spent inside places like the Art Museum so I could have a reason to be inside. I would like to go during nicer weather I think
Wendy T says
I want so much to take my son to Chicago this summer! It was interesting to see your post, since I’ve been thinking so hard about this lately. I’m not sure if I’d want to drive with him, or take the train.
You take really good pictures! I wish I had your eye for capturing images! I’ve never been to Chicago and your photos make me feel like I should go visit.
Great pictures of Chicago – you really captured a great sense of my city (I live here). Love the picture of the Bean!
We’re traveling as a family to Costa Rica this year. It’s the big blow out trip that we’ve been talking about – should be fun. Can’t wait.
what a fun trip! love that first pic with the reflection of you two lovely ladies! All the pictures are gorgeous and the rounded corners really set them off! I’ve never been to Chigaco!
These are some really cool shot and I hope to see them in real life. I am also sure being there with family made it even more special.Thanks for sharing.
JDaniel4's Mom says
You took amazing pictures. It looks like a wonderful trip!
Aw! What a fun time! I can’t wait to visit Chicago this summer!
Nicole (Mama to 4 Blessings) says
LOVE downtown Chicago, I haven’t been there since I was a kid but there is SO much to see, love the art museum best!
Looks like a fun time. We love visiting Chicago too.