A First Timer’s Trip to Chicago

We finally made it!

After years of flying through Chicago on our way to the east coast, we finally decided to make it our final destination and stay awhile.

And I have to say, I’m pretty glad we did! Chicago felt a lot like home. Obviously it should, since we live in the Midwest, but for the third largest city in America, it sure felt friendly! I couldn’t tell you how many people stopped to chat with Evelyn on the L or compliment her specs. Boy, did those Chicagoans just eat her up!

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

We arrived a little earlier than expected on a Tuesday evening, thanks to an impending thunderstorm that cancelled our original flight. But we were grateful to make it out of Omaha that day and not lose any time in our short 3 day itinerary.

We uber’d from Midway (about a 30 minute ride with traffic) to our Airbnb in Wicker Park. The 1 bedroom coach house apartment was just off the blue line that led straight to The Loop and was decorated with modern but cozy accents.

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean
Notes on the fridge from past guests // An Airbnb guidebook to help us fill in the gaps of our trip

After a quick trip to the local market for snacks and diapers, it was pushing Evelyn’s bedtime. So we settled in for the night, putting Evelyn to bed and ordering some Al’s Italian Beef for delivery (thanks, Postmates!).

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

Day 1

The next morning we caught a ride on the blue line headed downtown. We took the L most everywhere we went (except for a few occasions where we didn’t want to deal with the crowds during rush hour and opted to Uber instead). We decided to invest in the 3-day pass, which ended up costing $25 each after a new Ventra card fee. But it was worth it for us to not have to worry about refilling our cards with credit all of the time. And because we had the passes, we took advantage of the L a lot.

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

Buckingham Fountain & Millenium Park

Our first full day in Chicago was hot. Temperatures hovered in the low-90’s as we made our way towards Buckingham Fountain and Millennium Park from Jackson station. It was about 10 am by now, and heating up quickly, but we were able to shade ourselves in between buildings. I was surprised by how clean all the streets and sidewalks were, even in the heart of the city. And there was so much greenery too, between sidewalk trees and planter beds. It didn’t feel quite as “concrete-jungle”-y as other cities we’ve visited.

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

At long last, with no more shade in sight, we finally reached Buckingham Fountain. It was a welcome relief to stand in the path of the fountain’s mist.

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean
Jay Pritzker Pavilion in Millennium Park; what a gorgeous venue!

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

From there we made the trek north towards Millennium Park. A trip to Chicago wouldn’t be complete without a look into Cloud Gate, or “The Bean” as it’s more commonly called. We were surprised to find that it wasn’t too crowded yet. Evelyn, who normally loves to gawk at herself in the mirror, was a bit confused by the whole thing, and hardly cracked a smile.

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

Lunch in the West Loop

We popped over to the West Loop for lunch at avec. Evelyn, who seems to always be hungry and demanding food these days, enjoyed bits of my lamb burger and chilled lentil salad even more than I did. A friendly lady next to us was impressed. She said her son was on the “white diet”: refusing to eat anything but white bread and pasta. I couldn’t help but be appreciative of Evelyn’s healthy and adventurous appetite, even if it does mean eating full meals every 3 hours.

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

An Architecture River Cruise

Later that afternoon, after taking a break to cool off and nap at the Airbnb, we made our way back down to The Loop for a Chicago River Cruise hosted by the Chicago Architecture Foundation. It was so dang hot, pushing 100 degrees, that there was no way we could keep Evelyn out on the open air rooftop deck of the boat. Since we’d purchased tickets in advance and didn’t really have any spare time to change them for, we decided to tough it out. Matt was kind enough to let me stay up top and take photos while he and Evelyn played in the air conditioned salon below.

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

Unlike other cities where it feels like it’s building on top of building, the river fantastically cuts through the core of downtown so you can see every detail of the various building designs as you cruise by. Check out more photos from the river cruise here!

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

It didn’t seem to bother Evelyn too much to have 1 hour on uninterrupted daddy time. Although, we’ll probably have to do a re-do of the tour next time we’re in the city, since buildings are kind of Matt’s “thing”! We’ll make sure it’s during a cooler month.

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

25 Family-Friendly Things to Do in Chicago

Day 2

Early Breakfast at Little Goat

Our second day in Chicago brought cooler temps and even a few sprinkles of rain, thank goodness, since we had a lot more walking planned. But first, we started the day off with an early morning breakfast at Little Goat (in hindsight, not the smartest idea considering the day’s upcoming events). Since we couldn’t get reservations to Stephanie Izard’s famous Girl & the Goat (tip: they book up months in advance), her casual diner spin-off across the street was the next best thing.

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

Foodie Neighborhood Walking Tour

Later in the morning we hooked up with Chicago Food Planet’s Food Tasting and Cultural Walking Tour of the Bucktown & Wicker Park neighborhoods. What better way to get to know the neighborhood you’re staying in than by eating your way through it, amirite?

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

Bucktown & Wicker Park are adjoining neighborhoods northwest of downtown Chicago. Bucktown, being the more refined of the two, attracts young hipster families. Wicker Park, on the other hand, is more eclectic and a little rough around the edges, but changing quickly. North Avenue (running east and west) divides the two similar, yet distinct neighborhoods. (PS. In deciding where to stay for our trip, I found this article to be most helpful, and hilarious).

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

The tour covered 6 stops for tastings, along with a bit of history on the area and its residents. It was well worth the ticket price and our guide Jade was the sweetest. Read more on the full tour experience here!

Dinner Back in the West Loop

Oh, and if a full breakfast and 6 food tastings weren’t enough, we ended the day with dinner at The Publican. Needless to say, we could barely move after our food-filled day.

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean
“So…I know we just ate like 2 hours ago…but where’s the food?…”

Day 3

Lunch & Shopping in River North

Our last full day in Chicago was dedicated to the River North area and a walk along Michigan Avenue. Unfortunately for us, Evelyn didn’t have the same plan and threw fits off and on the entire day. We did get to stop at a few stores, including Eataly and the Crate&Barrel flagship, but we had to call it a day early when Evelyn’s temperament wouldn’t allow any more shopping. (Yes, there’s more to this story.)

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

Window Shopping in Bucktown

We’d thought about visiting the 360 Chicago Observation Deck at the top of the John Hancock Tower, but decided to scrap it after an already exhausting day. Instead, we took Evelyn back to the apartment for yet another nap, and then spent our last evening back in Bucktown, doing a little window shopping and treating ourselves to a Mindy’s iced hot chocolate for dinner. When my shoe decided to break while walking down Damen Avenue, it was the last straw. We took it as a sign to call it a trip and hobbled back home.

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

Despite a busy three days, we never felt overwhelmed by being in such a big city. Unlike New York, where everyone seems to be in such a rush all the time, we didn’t so much get the feeling that we were “in the way” here in Chicago. Even during rush hour, when the sidewalks and trains were packed, everything still seemed pretty orderly. We were lucky to stay a little ways outside of the city center where we could escape each night to a calm and quiet neighborhood, which helped some too.

How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

All in all, it was a great first timer’s trip to Chicago! We’d accomplished what we set out to do: get familiar with a few different neighborhoods, eat some great food, and do a little sightseeing in between. We’ll be back for sure, and when we are, we’ll be ready to hit the ground running again!

25 Family-Friendly Things to Do in Chicago

What do we need to see next time we’re in Chicago??

Read Next: Kid-Friendly Guide to Eating Well in Chicago

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How to spend 3 days in Chicago on a first-time trip. // Family Travel | Travel with Kids | Midwest Travel | Chicago Itinerary | Where to Eat | Things to Do | Where to Stay | What to See | Chicago River Cruise | Magnificent Mile | Wicker Park | The Bean

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