Chicago Adventures

At the beginning of April, I went on a work trip to Minneapolis. The best part about that work trip was that I got to tack on personal travel to Chicago for a girls weekend with my gym friends, Jen (the one who lives in Canada) and Ashley.

Here’s my weekend recap, which you may have already read about weeks ago in Jen’s recap posts here and here. Also, a lot of picture credit for the photos in this post go to both Jen and Ashley. My phone was uncooperative at many points during the weekend, so I made them send me pictures I could steal and use for F&F. Thanks ladies!

Chicago Adventures

I landed around 3pm on Friday and found Jen at the Starbucks at the “base of the Y” at my terminal. Get it? We decided to meet at the base of the Y in the airport because in real life we met in the basement of the Y. Yup, we’re cool. I was so excited to see Jen after not seeing her since her wedding that we had several elevator and train and even walking mishaps on the way to the hotel, but it didn’t even matter because the street smelled like brownie sundaes and we were all yayy and chatty and reunited. Don’t ask.

Once we found Ashley (who had already taken care of check in and the most important job of buying SNACKS), we walked down Michigan Ave to the Signature Room in the John Hancock building to start our weekend off right. By that I mean ordering pink cocktails with a view.

Chicago: Signature Room

Chicago Signature Room

Chicago: Signature Room Ashley and Me

For dinner we went to a Mexican restaurant called Mercadito, where I had one of the most delicious margaritas I’ve ever had in my life.

Chicago: Mercadito Margaritas

We were psyched to snag patio seating, even if limited to only 90 minutes. We ordered chips and guac (duh) and three different kinds of tacos to share. They didn’t disappoint.

Chicago: Mercadito TacosI think the best part of the weekend was just hanging out, relaxing, and talking over good food!

Chicago Margaritas at Mercadito

After dinner, we continued on to a piano bar called The Redhead. This place made me think of my friend Bridget because she’s a ginger.

Chicago: The Readhead

We were hoping for a slightly different scene (aka more dancing, less old people), but we hung out for a bit while sipping really strong (too strong) martinis. Then we laughed about being old women drinking martinis at a piano bar. Shoot. Finally, our last stop was back at our hotel bar. This place had every possible chair, sofa, loveseat, and ottoman combination you can think of, all set up in different places, so naturally we had a little fun with that.

On Saturday we woke up and grabbed bagels before going on our bike tour! Since we were doing the Bikes, Bites, and Brews tour, we probably didn’t need to carb up before carb loading all day, but what fun is vacation without extra carbs?

Chicago: Bobby's Bike Hike
Backing up for a minute: when Jen and Ashley said they wanted to do a bike tour, I was REALLY nervous. Like really, really nervous. I hadn’t ridden a bike since I was fifteen years old, and I was honestly having a bit of anxiety about navigating through the streets of Chicago. I gave myself a pep talk though, and made myself follow my own advice about getting out of my comfort zone. This is silly to admit, but to prepare I went over to Slesh’s apartment and had her watch me ride her bike in the parking lot down the street. Yup. It was like I was a six-year-old child learning to ride a two-wheeler for the first time. I guess you can only ask your best friend for help with something like that.

Text

But just for the record, the saying really is true. It’s like… riding a bike. You don’t forget how. Our lesson lasted about five minutes, and I was fine, but I’m glad I did that to ease my nerves before gracefully cycling through city streets.

Here are some scenes from our bike adventures:

Chicago: Bike Tour

Jen got to wear the reflective vest because she volunteered to be safety patrol and bring up the rear of our tour! She’s so responsible.

Chicago Bike Tour

Our tour had three scheduled food stops along the way. The first was at Gino’s East for deep dish pizza. Deep dish pizza with corn bread crust, might I add.

Chicago Bike Tour: Ginos East

The second was for dessert at an awesome cupcakery called Swirlz. The cupcakes were to die for.

Chicago Swirlz Cupcakes

And the third food stop was for a Chicago style hot dog at a place called Murphy’s Red Hots. No ketchup, lots of toppings.

Chicago: Hot Dogs at Murphys

Aside from the food, we stopped a couple of times along the way for some photo ops. I do wish the tour guide gave us a little more background on Chicago history or fun facts about the neighborhoods as we biked through, but I think the other tours are better suited for that!

Chicago Bike Tour2

The end of the tour included two stops for beers. The first was in the Wrigley Field area. I was so excited for this part because my Yiayia grew up in Chicago and was always a fan of the Cubs!

Chicago: Wrigley Field

Chicago Wrigley Field

The first bar stop was at Murphy’s Bleachers, where I tried the Three Floyd’s Gumballhead. Wheat beer + citrus = yes.

Chicago: Murphys Bleachers

The second beer stop was at a restaurant called RJ Grunts. This place apparently invented the salad bar? I wish we could have stayed longer there, and I also wish we got more than just an itty bitty pour of beer.

Chicago: RJ Grunts
Finally, our last stop of the bike tour was along the water. Pretty views!

Chicago along the water

After our bike tour, we headed back to our hotel to drink prosecco, eat snacks, and jam out relax, clean up, and get changed for the night.

Chicago: Snacking

For dinner we ate at Gene and Georgetti, a really old school steakhouse that Ashley’s family has connections with. We continued our day of eating with big salads, (huge) steaks, asparagus, and a bottle of red wine.

Chicago: Gene and Georgetti

Chicago: Gene and Georgetti's

After dinner, we continued on for more wine at a more modern steakhouse and bar, Chicago Cut. Loved the vibe here, and we could browse the menu on an iPad. Fancy shmancy.

Chicago DrinksFinally, we finished our night at a Second City comedy show (no pictures!). Since all three of us are trying to save money, we opted to go to the hour long post show for free at 1am after the main showtime, but I really really wish we had just splurged on tickets to the real thing because we were laughing so hard.

The next morning we woke up and headed to a place called Rockit for brunch. Mimosas were a must, and I ordered a California omelette (WHY are omelettes with guacamole the best?) and one of the best side fruit salads I’ve ordered. A side fruit salad is solid in my book when it has more than just honeydew melon in it. Amiright?

Chicago: Rockit

We only had a couple of hours left to walk around the city before we had to catch our flights, so we did a little tourist action at Millenium Park and at the bean.

Chicago: Millenium Park

Chicago: The BeanChicago: The Bean

Chicago: Touring

We did a little more walking around and finished our day at Ghirardelli’s for some chocolate in beverage form.

Chicago: Ghirardellis

It was such an awesome weekend, but as expected, it FLEW by. I felt like the second we got there it was time to leave! I was really sad to have to part ways with the girls on Sunday (especially my sad hug goodbye with Jen in the airport), but after being away from Tim and home for a whole week, I was happy to be home. I love traveling and getting away, but there’s just nothing like that feeling of landing back in Beantown.

–Let’s chat–
Have you ever been to Chicago? What’s your favorite part of the city, restaurant, or thing to do? When’s the last time you rode a bike? Also, when can I go back to Chicago?!

I think I could live there!

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11 thoughts on “Chicago Adventures

  1. Thank you for a great whirlwind tour of Chicago. You are a natural-born writer! Maria Mannix

    ________________________________

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  2. I haven’t been to Chicago since I was about 12 or 13 – not nearly as fun of a tour as your’s!!
    Y’all’s weekend sounds like so much fun – lots of great food and drinks while spending time with good friends – perfect!!

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  3. What a nice recap of your trip! I am so glad you ladies had fun! I hope to plan a trip to Chicago very soon to visit my brother who just moved there, you bet I’ll be asking for suggestions on things to do and see while I’m there. Its also seriously on my bucket list to take a selfie at the bean, does that make a loser?

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  4. Love it!!! I went to Chicago in November and fell in love with the city. I didn’t do any of the things you girls did, but wish I had (ok, I went to the Bean, that’s right)! I’m going back in july and can’t wait πŸ™‚

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