Weekend Getaway

Five Reasons I Fell in Love with Chicago

In case you couldn’t from my week of posts all about my trip to Chicago — I totally fell in love.

Chicago River & Navy Pier | Our Streamlined Life

The city first came on my radar a few years ago when I started noticing some of my favorite online ladies (Jess Lively, Jessica Murnane, The Everygirl) were all based out of Chicago. Not only did it seem to be a great spot for thriving and aspiring entrepreneurs, but their Instagram pictures were regularly full of gorgeous city views and hunger-inducing food.

“But,” I thought, “Who wants to live in Illinois, anyway?”

I’m not entirely sure what I expected to experience when I got there, but I did not expect to love Chicago as much as I did. I figured it would be a fun weekend getaway; I’d enjoy myself for a few days, then check it off my list and move on.

I guess I should caveat my list below by saying I did visit Chicago in late June — from what I’ve heard, the best possible time to be there. I might be singing a different tune if the city had been in the throes of one of its famously harsh winters.

My sister lives about three hours from Chicago and when I professed my love for the city she looked at me in total disbelief. “We never go to Chicago, if we can help it,” she told me. “If we want to do the city thing, we always go to St. Louis.” Clearly, to each her own.

Ryan and I have shared before that part of our journey is trying to figure out where we want to settle down. And while we haven’t yet answered the question of whether we want to live in the city or the country, if we were to move to a city, Chicago is just the kind of place I can see us heading. Read on for my top five reasons why.

1. Chicago is Full of Urban Parks & Green Spaces

I love the city but I also love nature — making a city full of parks the best of both worlds. (That’s the reason I love Philadelphia and Savannah so much!) I love the feeling of being surrounded by trees, grass, and water, while simultaneously being within walking distance of work, home, and modern conveniences.

Chicago is full of parks, big and small — from Millennium Park to Lincoln Park. In fact, it has more than 8100 acres of green space, with 600 parks and 11 beaches. And the Chicago Riverwalk and the Lakefront Trail make it easy to get close to the water, too.

Chicago River | Our Streamlined Life

2. Chicago is an Active City

Everywhere I went in Chicago I loved seeing all the people out enjoying the beautiful weather, from runners in the park to bikers on the Lakefront Trail. Many cities have a vibe of rush rush rush, everyone hell-bent on getting from point A to point B (and usually wearing headphones to drown out the outside world). In Chicago it seemed like everyone was just happy to be outside … probably a byproduct of those crazy winters!

On a related note, I also appreciated that most of those people who were out and about seemed to be people who lived or worked there. I always find it a little off-putting when I visit a city and find nothing but tourists as far as the eye can see (however hypocritical that might be). Chicago was full of natives out enjoying playdates in the park or a lunchtime run. I love a city that the locals seem to love, too.

Divvy | Our Streamlined Life

3. Chicago is So Clean

If you’ve visited New York, Boston, or Philadelphia in the summer, you’ll appreciate this one: Chicago doesn’t smell like trash. That’s due in large part to its 1900 miles of alleys, which keep garbage and other messy parts of city life out of the main thoroughfare. (This article about this “utilitarian wonder” is super interesting.) It was also the first American city to have a modern sewer system, which probably has something to do with it too.Downtown | Chicago Our Streamlined Life

4. Chicago is Like an East Coast City … but Friendly

Despite the trash comment above, I’m partial to east coast cities like New York, Boston, and Philly — maybe because I’m an Irish girl who loves a good pizza. That said, none of those cities are renowed for their warm, welcoming locals. Chicago had all the feel of an east coast metropolis, but just about everyone we encountered was — wait for it — friendly and helpful. The best way I can think to describe it is an east coast city with a midwest heart. It’s the best of both worlds!

Willis Tower Daniel Burnham | Our Streamlined Life

5. Chicago Has Something For Everyone

Chicago has something for everyone — maybe because it boasts 77 unique and distinct neighborhoods. I hadn’t realized just how big the city is; in my head, I’d always compared it to Boston in size, but at 234 square miles, it’s actually five times Boston’s land area! We spent most of our time in The Loop & River North area, but that’s just scratch on the surface of everything Chicago has to offer. This is a great resource on Chicago’s neighborhoods, and apparently “This Infographic of Chicago Neighborhood Stereotypes Nailed It.”

Read my other posts about Chicago here, here, and here!

I loved Extra Pack of Peanuts’ Destination Diaries – Chicago. Travis is joined by a Chicago native, and he has lots of great recommendations for food and beer. This episode came out right after I got back from Chicago — I think he was there right around the same time I was.

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

Five Reasons I Fell in Love with Chicago | Our Streamlined Life

Just One More Day: 6 Things I Wish I’d Done in Chicago

Yesterday I shared all the fun my sister and I had during our three days in Chicago (part one, part two) … but there’s so much more we could have done! I hadn’t even left the city before I was already scheming about everything I would love to do next time I visit Chicago.

1. Take a Chicago Crime Tour

My interest in organized crime and the twisty politics in Chicago was first sparked when we binge watched Kelsey Grammer’s terrific-but-short-lived show Boss a few years ago. And of course Chicago has a rich and storied history of criminals, mobsters, and gangsters. Chicago Crime Tours merges crime and history to show you famous landmarks showcasing criminals from Al Capone to H. H. Holmes.


Chicago Crime Tours | Our Streamlined Life

2. Kayak on the Chicago River

I absolutely love the idea of urban kayaking, and paddling down the Chicago River through the heart of the city sounds like an awesome way to see the city! Wateriders offers everything from history tours to fireworks paddles — you can even combine crime and kayaking. Pretty sure it doesn’t get more fun than that.

Kayak on the Chicago River | Our Streamlined Life

3. Take a Chicago Architecture River Cruise

Another way to see the river and the city is with a Chicago Architecture Foundation River Cruise. We went back and forth between doing this and a Lake Michigan boat excursion; we ultimately opted for the lake cruise because it seemed a bit more kid-friendly, but next time I’d love to take in Chicago’s tremendous architecture from the river.

Chicago Architecture Foundation River Cruise | Our Streamlined Life

4. Visit a Distillery (or Two!)

We had an awesome experience at CH Distillery, and that just whetted my appetite for Chicago’s distillery scene. Koval has a dry gin I’d love to try, and a full calendar of special events; Rhine Hall specializes in fruit brandies and offers tours, tastings, and brandy cocktails. And both spaces look awesome, which is definitely a plus.

Rhine Hall | Our Streamlined Life

5. Enjoy a Chicago Brunch

Just about every article I read about Chicago practically screamed, “YOU MUST EAT BRUNCH WHILE YOU ARE THERE.” We didn’t end up brunching, but I’d love to check out a few mouthwatering places next time I’m in town. The Hampton Social offers a relaxed nautical ambiance and fresh coastal menu. Fig & Olive offers a — wait for it — fig & olive salad, which looks tremendous … and hello, blood orange mimosas. And Waffles Cafe has waffle flavors you never knew you needed to try. (Mexican Chocolate Waffle, please and thank you.)

Fig & Olive | Our Streamlined Life

6. Run or Ride the 606

I’m kind of obsessed with rail trails, and The 606 is the best kind: a combination elevated rail line and park. Running through the Logan Square, Humboldt Park, Bucktown, and Wicker Park neighborhoods, it reminds me of the High Line, one of my favorite features in New York City. Read more about The 606 here.

The 606 Humboldt Blvd Lookout | Our Streamlined Life

Have you been to Chicago? What’s on your must-do list?

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

Just One More Day: 6 Things I Wish I'd Done in Chicago | Our Streamlined Life

In Love with the Windy City: My Girls’ Trip to Chicago (Part 2)

Read Part 1 here!

Our game plan for Thursday was to use Divvy to see as much of the southeast part of the city as we could.  Our first destination was Michaela’s only itinerary request: Skydeck Chicago at Willis Tower.

The Skydeck is a pretty touristy stop, but it was really cool — and the glass ledge was unexpectedly heart-stopping.


By the time we descended from Willis Tower, we were ready for lunch, so we hit up a Chicago classic: Giordano’s pizza. I’m gluten-free but I threw caution to the wind for the opportunity to try true Chicago-style pizza for the first time. It was pretty good, but I’d have to say I prefer New York style. We ate at the 223 W Jackson Blvd location just up the block from Willis Tower, but you can find Giordano’s locations all around the city.

Our next stop ended up being kind of a funny failure. As we headed to our next Divvy dock to pick up another bike, we saw a Chicago Public Library bus.

“Hey!” I suggested. “We should go check out the library! I bet it’s pretty awesome!”

“Um, yes,” Michaela — a fellow book lover — responded.

So, we put “Chicago Public Library” into Google maps and away we pedaled.

Word to the wise: When you put “Chicago Public Library” into Google maps, you will indeed end up at a library. But it will be the one in Chinatown. No one will speak English and you will be far away from everything.


There was a pretty awesome mural at the Chinatown branch, and we used their bathroom and picked up new bikes, so it wasn’t all bad. The ride was actually quite nice, too — the streets were quieter and there were dedicated bike lanes in many areas. I was a little apprehensive as we pedaled south, on the alert for anything that looked like the Chicago crime ghettoes constantly showing up on the news, but as far as I could tell, we didn’t end up anywhere sketchy.

That little detour completed, we did some research and found out that the library we really wanted to see was the Harold Washington Library Center. If you’re looking for it, it’s at 400 S State Street, which is not in Chinatown 😉

Harold Washington Library Center
Photo from

The building is totally awesome, and you have to go to the 9th floor and check out the Winter Garden. It is amazing, and I can only imagine how wonderful it is to have a beautiful green place like that to go during cold Chicago winters.

The only thing I love in a city more than pizza and books is lots of green spaces — and again, Chicago didn’t disappoint. Our next stop was the parks: Grant ParkMillennium Park, and Buckingham Fountain. Tragically, my phone was totally dead at this point, so no pictures, but the weather was perfect and the parks green and expansive.

At this point we hit our first Divvy snag: we wanted to pick up new bikes after visiting the fountain, but all the nearby docks were empty. At one point we found a dock with two bikes, but one had an error message and couldn’t be undocked. Womp womp. We had planned to head north up the Lakefront Trail to check out the beach, but without bikes we realized we’d probably have to make our way back in the dark. Instead we decided to return to our hotel rooms, clean up, and figure out what we wanted to do next.

I’m not a beer-drinker, but I get pretty excited about gin — so when I found a distillery a couple miles from our hotel, we decided it would be the perfect way to top off our evening. Back on the bikes we hopped, pedaling about a mile and a half to Randolph Street and the CH Distillery.

CH Distillery | Our Streamlined Life

The ambiance was really cool — behind the bar was a huge window looking into the distillery! — and the drinks were seriously awesome. I had a classic gin & tonic, to give their gin a true test run, and it was terrific. I also tried the Baby Sharks, made with strawberry, cucumber, and red pepper — perfect. We chose to Uber home instead of biking in the dark, much to the amusement of our driver: “Ya’ll coulda walked!

Friday we were joined in the city by our sister Bridget, who made the drive from Peoria with her boys to visit us. In the spirit of a 7-year-old-boy-friendly adventure, we spent more time in the park, had pizza and ice cream for lunch, then opted for a boat tour. We did the Shoreline Sightseeing Classic Lake Tour leaving from Navy Pier, and we all had a blast.

Chicago Skyline from Lake Michigan | Our Streamlined Life

Sadly, once our boat docked it was time to head back to the airport. As we drove I was already scheming ways to get Ryan to come with me to Chicago. Stay tuned for my list of things I wish we’d had time to do in Chicago … and all the reasons I loved it so much!

That’s everything we did, saw, and ate during our three day girls’ trip to Chicago! Have you been to Chicago? How would you rank it?

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

In Love with the Windy City Part 2 | Our Streamlined Life

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