Chicago With Kids: Weekend Trip to Chicago with a Toddler & Preschooler: Child-friendly destinations, traveling without baby gear and flying for free!

How we managed to stay dry, hands-free when it rained!

Before having kids, my husband and I loved to travel. We would always pick a new and exotic international place to visit one time a year. Of course, before having kids I envisioned the parent I was going to be and had a long list of “when I’m a mother I will never…” It’s funny how things quickly change once you become a mother! Traveling with two kids is no easy tasks and never really feels like a vacation (be sure to check out my Travel Tips & Toddler Airplane Activities to help make your travel experience as smooth as possible). Once we had our second child, we put off traveling for a whole year because we would both become so overwhelmed with just the thought of what we had to bring, let alone the actual travel. Anyway, we are back at it. We decided to see what Chicago, IL had to offer. It seemed like a convenient city to navigate while providing a lot of fun places to experience. We opted to not rent a car and just walk everywhere with our stroller. Because of this choice, we picked a centrally located hotel, near Millennium Park.

Hotel: Comfort Suites Michigan Ave. Loop 320 N. Michigan Ave. Chicago, IL 60601

We rented a suite with a separate bedroom and spectacular views of the city. Note, some of these bedroom suites have a door to close and some of them are open to the living room. I wished I would have known this prior, but we made it work. We always either rent a hotel with a separated room of some sort or rent a house through www.airbnb.com. Our children go to bed before we do and it’s nice not to have to sit in the dark in a hotel room.

The location was perfect. We were a 5-min. walk away from the Bean at Millennium Park and about a 15-min. walk away from the Maggie Daley Park.

The hotel provided a pack n’ play, so we did not need to travel with one. We requested extra blankets and pillows and made a little floor-bed for our three-year-old. She is a crazy sleeper and cannot be trusted on a bed without rails! Because the bedroom was not completely closed off with a door, I used a large industrial black trash bag (that I stored our stroller in during gate check at the airport) tapped to the doorway, to block out the light in the living room.

Getting Around: Once we flew into Chicago Midway International Airport, we took the CTA Orange Line train into downtown. It was very easy to find and navigate. We had no problem taking the stroller and our luggage on, however; our exit (State/Lake) was not stroller accessible. This made things very tricky. We had two kids, a stroller and luggage to carry down a huge flight of stairs. I would ask the hotel concierge to confirm your train exit to see if it is stroller friendly AND the best streets to take when you are navigating the city. We found our self a few times having to carry a double stroller up and down several flights of stairs due to the bi-level nature of this city. We were told the further north we walk, the flatter the ground. Once we figured that out, navigating the city with the stroller was easy.

Places we visited during our stay:

• Navy Pier: They had an amazing water fountain in the front for the kids to run through, a kids museum, waterfront restaurants and bars, cruises, carousel, Ferris wheel, and rides.

• Shedd Aquarium: This place is wonderful! They had a section to touch stingrays, a few Beluga whales, penguins, freshwater fish, saltwater fish and everything in-between. You can easily spend hours there. Near the Aquarium is the planetarium and the Field Museum, which we did not have time to visit. It was about 2.5 miles from the hotel we stayed in.

• Wendella Boat Tour. We tried our best to do the night architecture tour (because we heard the view of the city lights are amazing). We bought tickets but had bad luck with the boat on that day. They were running late and with two littles, it was just getting too late and too close to bedtime.

• Millennium Park: this is such a cool space! There is the bean at cloud gate, the Jay Pritzker Pavilion and Crown Fountain (a great space for the kids to splash around in as well as an amazing work of art). The park offers much more, but this is all we had a chance to do. There was also The Plaza at Millennium Park, which is an outdoor beer garden, near the Crown Fountain. It was a great place to let the kids run around, while mom and dad got a chance to cool down with a drink.

• Maggie Daley Park: we visited this space twice. Hands-down, the best park I have ever been to. They had multiple playground sections for several different age groups and some water features as well. The whole family had a blast here. The first time we visited the park it was drizzling and not a soul there. The metal slides became a daring adventure.

Top Chicago Eats:

• Lou Malnati’s (my favorite deep-dish spot): there was a 45 min. wait to be seated. We were able to place or pizza order ahead of time, while we waited for our seat. We took the kids for a walk around the city and came back when our table was ready. When we were seated, the pizza took about 20 min. to come out.

• Gino’s East (my husband’s favorite deep-dish spot): since we were seated right away, we had to wait for 45-min. for our pizza to be ready.

• Portillo’s: we have one in Southern CA, but it is about an hour away from where we live and since it’s home to Chicago, we figured we might as well. They have amazing dogs and sandwiches.

How we Flew for free:

• We signed up for a Southwest credit card promotion. This is the second time we have used it. It requires you spend a certain amount of money on the card during the first several weeks. Upon doing this, you receive travel points AND a companion pass.

Your companion can fly FREE for two years. It’s a great deal. I believe this deal is offered a few times a year. We found out about it through www.slickdeals.com, but I am sure you would also be able to find out about it through the Southwest website. My husband and I both signed up for the card promotion, so we assigned our children as our companion.

• We used Expedia.com to find a great deal on our hotel.

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Chicago With Kids: Weekend Trip With Toddlers

Chicago With Kids: Weekend Trip to Chicago with a Toddler & Preschooler: Child-friendly destinations, traveling without baby gear and flying for free!