Wednesday, December 9, 2015

Christmas in Chicago

We got to spend the weekend in Chicago a few weeks ago visiting friends.  It was the perfect time of year to visit because the city was kicking off all things Christmas.  The Magnificent Mile Light Festival was going on that weekend so downtown was all a buzz.  We got to enjoy the fun and have some fun of our own.

Traveling in a big city with a toddler or kids isn't for the faint of heart!  I worked really hard to pack as light as possible, but there are still a lot of must have to lug around - pack n play, snacks, entertainment items, favorite things, etc.  We had a great time, but it's definitely not a relaxing vacation to travel with little ones.  You make tons of great memories, have a lovely time and are exhausted by the end of it.  It's always worth it and it helps when you plan ahead.

8 TIPS for Taking Toddlers to a Big City:

1. Pack as little as possible 
- One bag per person because you'll likely have to park off site, haul your bags a few blocks or get dropped off a the hotel entrance with your bags while one of you goes and parks.  The valet helped us get our things up to the room, but we carried it all back to our car when we checked out.  The stroller worked great to help carry things, but it was still a lot to mess with.
2. Be a minimalist & limit multiple items 
- Rewear shoes, one jacket, one scarf, etc.   Wear comfy walking shoes!
3. Bring your child's comfort items - bunny, paci, blanket & pillow
4. Pack snack
- It was hard to find places that were really easy to get in and out of without waiting in a long line so it was really handy to have a sippy cup & lots of toddler snacks.  That way she was always well fed, not thirsty and we didn't have to hunt down food for her.  I also had some granola bars & candy for the adults.
5. Stay in a hotel that offers room service or has a restaurant on site
- You never know when your plans will change last minute so it's nice to have the option to stay in for a meal
6. Be prepared to fold up your stroller and leave it at the front of the restaurant
- Our stroller has a large basket so I put my diaper bag in it and one other oversized bag to hold things.  That way we were able to leave our stroller, but still take our belongings/purchases to our table.
7. Check and recheck the weather before you head out so you are prepared
-Bundle up, bring umbrellas (or wear hoods since it might be really windy) and stay cozy
8. Don't pay to park at your hotel 
- Search online for better/cheaper parking options nearby and leave your car there for the weekend.  Try to avoid driving in the city if you can.  We opted to use Uber a few times and it was so nice to not have to worry about navigating a new city.

The weather was a mixed bag which is probably pretty typical for Chicago this time of year - snow, rain, sun, clouds and lots of wind.  We drove north 3.5 hours and arrived before any snow on a Friday evening.  My husband gets all of the credit for navigating in a new city because I wasn't much help.  I am usually really great with directions, but found myself completely turned around all the time.  Olive enjoyed her books, snacks, Christmas music and the city scenery as we drove.  We try to hit the road around nap time if we can that way she can nap and we can have some time to chat/enjoy the trip.

I did some research ahead of time, my hubby bought some groupons and I consulted my friend Kelly who lives in the city with her two little ones.  All of this was really helpful in planning a fun trip.  It was especially helpful to hear insider tips from someone who lives in the city you're traveling to. 

Check in later today for a post on our restaurant recommendations for Chicago.

We stayed on Michigan Avenue at The Warwick Allerton.  It was a really great location for us.  We unloaded our stuff in the room and Olive quickly made herself at home in our bed.  The rooms are advertised as small/cozy and ours just fine for the three of us.  Everything was really nice and we had plenty of room for the packnplay, stroller and our bags.

It started snowing right after we finished our first dinner in the city.  It was so much fun and Olive was mesmerized by it.  People were all a buzz with the first snow of the season and I'm sure it's much less exciting come February.

 Kevin insisted that we order room service dessert one night and who am I to say no.  We had a delicious brownie + ice cream sundae.  Olive was so thrilled about the whole thing that she opted not to go to bed until 11:00.

 We came fully prepared for the cold, but not the rain.  Our one umbrella was looking pretty sad after walking for miles and miles.  Good thing we all we wearing layers and had hoods.  People don't really make way for strollers so it was challenging at times to navigate the crowds.  Also, if we'd been really prepared for rain, we would have purchased a rain cover for our stroller like all of the city people had for their strollers.  Good thing ours has a large canopy.

We had fun browsing all the souvenirs at The Disney Store and ultimately decided on a pair of Mickey and Minnie Christmas stuffed animals.  Olive insisted on holding her bag.

 We walked everywhere, but the rain and snow got so intense that we opted to give Uber a try.  It worked out great and we used it several more times.  Olive had never ridden in a taxi or car service before so it was another fun "ad-ben-ture" in the city.

 The Light Festival Parade was going on right outside of our room.  It was 20ish degrees and super crowded so we opted to watch from our room.  We played the parade on the TV so we heard the music and saw everything up close.  The lights on Michigan Avenue turned on as the parade was making its way down the road.  It was a lot of fun to see.

 We headed out for some adventuring, dinner and sight seeing all bundled up again.  Off to try to find some delicious pizza and maybe some Starbucks.

 We woke up to a frosty morning and enjoyed hanging out in our room.  We debated ordering room service breakfast, but opted to get out and about instead.  Gloves, scarves, blanket and lots of layers later we were on our way.

 The trees, floral arrangements and Christmas decor was just lovely wherever we went.

The wind turbines in Northern Indiana were definitely a highlight for Olive.  She counted them, was so curious about them and loved seeing them for miles.


  1. What a fun trip! Great tips, too! We went to Chicago before Wesley was born. It was in the fall, and it was so fun because we were right across from the Lincoln Park Zoo!

  2. Fun! Traveling with a busy little one is such a handful- looks like yall rocked it and packed in tons of fun!

  3. So much fun. I love that even pregnant and with a little you are still having fun and making great memories together. I can't wait to see our first snow, that first one is always so magical!

  4. SO cute! Chicago is a fun town. I wish Evansville still had their Disney store..that was one of my favorites.

  5. Looks like you guys had a blast! Love the tips. Especially about the hotel having food - something I wouldn't think about, but you have to stop those hangry toddler (or pregnant lady) meltdowns quick. And venturing out is never quick.


I LOVE hearing from you!! Thanks for taking the time to leave sweet comments; I enjoy reading every one of them.