In Love with the Windy City: My Girls’ Trip to Chicago (Part 1)

It seems like my sister Michaela and I have been trying to plan a trip together forever. Somehow, between the fact that she’s a crazy working girl and I’m always headed somewhere with Ryan, we just never made it happen. After Ryan and I skipped Chicago during our fall road trip, I was determined to get there — so I picked some dates, booked my tickets, and begged her to join me.

In Love with the Windy City | Our Streamlined Life

Chicago had been on my travel wish list for a while, and #spoileralert: I ended up falling totally in love. Read on for everything we did during our three day-trip: getting to Chicago, getting around Chicago, and what we did (and ate!) while we were there.

Getting to Chicago

I booked my tickets about a month in advance on Southwest. I’m super spoiled because our closest airport is Baltimore-Washington International (BWI) — Southwest’s eastern hub — making it super easy, and usually inexpensive, to get just about anywhere. After LUV rewards points and some flight credits I’d been saving, I paid $44 for a direct, two-hour flight from BWI to Chicago Midway. (Without those credits, the round-trip ticket price would have been just about $250.) Michaela’s flight from Boston and mine from Baltimore arrived around 10:30pm and we headed straight for the no-frills airport hotel I’d booked.

Getting Around Chicago

I’d gone back and forth about transportation options prior to the trip. I considered booking a rental car, but the cost quickly added up as I calculated rental costs plus parking and gas expenses. Adding in the stress of city driving, I decided to skip it and hope for the best when it came to taxis and public transportation.

In the end, Uber was our best friend. We used it to get from the airport to downtown, then for a few quick trips around the city. It was cost-effective and super easy — we never waited more than 5 minutes for a car, aside from one botched attempt to get picked up at Navy Pier. If you haven’t used Uber before, you can sign up here and use the code rebeccar7085ue to get your first ride (up to $20) for free! I used someone else’s signup code to get a free ride, and Michaela used mine, so we actually got a few free rides out of the deal and I can’t speak highly enough about the clean cars, friendly drivers, and overall excellent experience we had with Uber. I was a little nervous to use it for the first time, especially as a couple of girls in an unfamiliar city, but we had a very positive experience.

The other method of transportation we relied on was Divvy, Chicago’s bike sharing service.


A photo posted by Michaela Reichl (@michaelareichl) on

A 24-hour Divvy pass is $10 for unlimited 30-minute trips. I was afraid at first that biking in the city would be super scary, or that we wouldn’t be able to find docks everywhere we wanted to explore. But after a few shaky moments I realized Chicago drivers were used to bikers in traffic — and we never had a problem finding a dock (there are hundreds around the city). And even if you can’t quite bite the bullet on bike riding in traffic, Divvy would also be an excellent option for riding the lakefront trail.

What We Did: Three Days in Chicago

We got up not-too-early (this was a vacation, after all) on Wednesday morning, and I used Priceline Express Deals to book our two nights in downtown Chicago. We electronically hailed our first Uber to bring us downtown, and our ride arrived in no time.

My love affair with Chicago began the moment we hit Lakeshore Drive. The sky was a ridiculously bright blue, the waters of Lake Michigan were clear and shimmering, and the Chicago River was a gorgeous green. 


It was barely 1pm at this point and our hotel room wasn’t ready yet, so we dropped our bags and headed off to find lunch. Our quick walk to Navy Pier took us past several parks full of Chicagoans out enjoying the sunshine. I was already loving the green spaces that seemed to be everywhere, right in the heart of downtown.

We both hungry after our lackluster breakfast at the airport hotel and quickly opted for Mexican at Chango Loco Mexican Cantina on Navy Pier. It may not have been an “authentic Chicago” meal, but we were pretty darn happy to sit outside on the pier and enjoy the sunshine.

After lunch and a stroll around the pier, we both admitted to being pretty tired. We both had been fighting colds all week and were definitely dragging. In the true spirit of vacation we decided to head back to our room and took a tremendous nap that lasted till dinner time.

First stop: up to our hotel’s 42nd floor to check out the view. It did not disappoint.

Chicago River & Navy Pier | Our Streamlined Life

In lieu of dinner, we headed to Ghirardelli for ice cream. Let me just say — that place is awesome. They give you free chocolate just for walking in the door, and the ice cream sundaes were delicious!

Then we headed back to Navy for a ride on the Centennial Wheel. Fun facts: the wheel is 196 feet high and has 42 gondolas, is the sixth tallest Ferris wheel in the United States, and can withstand winds of 115 miles per hour.

With unplanned perfect timing, we boarded the wheel just as an epic fireworks show began, giving us a tremendous view from the sky. It was the perfect way to end our first evening in downtown Chicago!


Come back tomorrow to read Part 2, which includes biking, boating, and boozing!

For more ideas on things to do in Chicago, check out our Chicago Pinterest board.

In Love with the Windy City Part 1 | Our Streamlined Life

I'm the oldest of 12 crazy kids and two pretty awesome parents. My love of travel developed during my early years traveling the globe as an Air Force brat. I'm a runner, a writer, and a reader, and I love cooking up good food and cozying up our camper.

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