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.


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!

Portland, Maine: Eats & Drinks

Tonight I finally got around to uploading all my vacation pictures from Portland.  And then I got sad because I want to be back there.  Wah.  Anyways, here’s a recap of all the yummy food and drinks we had during our week away!

Portland Eats & Drinks

Before leaving for Maine, we reached out to everyone we knew for restaurant recommendations.  We got so many recommendations that we didn’t know what to do with all of them!  We tried our best to make it to all the big ones, but we’ll just have to go back to get to them all.

One of the places that almost everyone said we had to stop at for a casual meal was Duckfat, a small little sandwich place right down the street from our hotel.  When we arrived on Monday it was pretty chilly and cloudy out, so we figured this would be a great place to grab our first lunch of the week.  It was a small restaurant, with some parties even sharing tables, but it definitely made for a unique experience!  I ordered the duck confit panini and Tim ordered a pork belly panini.  Both were delicious!  We also split fries.  I normally do not like French fries, as potatoes don’t really do anything for me, but I figured I at least had to try the infamous fries in duck fat.  And I did like these.  We also had our first beers to kick off the week!  They came in mason jars, which I loved.


The Garden Cafe at the Regency
After walking around the downtown Portland shops for a few hours on Monday, we stumbled across a cute little garden restaurant called The Garden Cafe.  This restaurant/bar is associated with the Regency Hotel, but it was the perfect place to hang out and get a drink.  So pretty!  I ordered a glass of wine and finished that up with the most delicious strawberry vodka lemonade.  I highly recommend this place for a drink on a nice day.

The Garden Cafe

On Monday night before dinner, we stopped at Sonny’s for a pre-dinner drink.  My friend Cristin recommended this place for its cocktails, and I enjoyed a glass of their house made white sangria.  We wanted to go again another time during the week, but we unfortunately never made it back.

Sonny's Restaurant & Bar

The Grill Room
Dinner on Monday was at The Grill Room & Bar, which was recommended to us by the bartender at the Garden Cafe earlier in the day.  After taking a while deciding whether to each get one big entrée or to go for several smaller dishes, we decided to just a few  smaller options.  First up were the oyster shooters, then wood oven baked brie, then two scallops, and last up was lobster pizza.  We both agreed that the brie was the best of the bunch.  I also think my stomach regretted ordering so much bread the next day!

The Grill Room & Bar

Gorgeous Gelato
On Tuesday we spent the day at Scarborough Beach State Park, so of course gelato sounded perfect after a day in the sun.  My co-worker Mike recommended Gorgeous Gelato, and it did not disappoint.  This place is owned by a family right from Italy, so you just knew the gelato was going to be good.  I ordered raspberry.  Yum!

Gorgeous Gelato

Gilbert’s Chowder House
Tuesday night after the beach, all we wanted to eat was chowder!  We headed to Gilbert’s Chowder House, which we heard had some of the best chowder in the city.  We both got pretty big cups of seafood chowder, so that’s all we needed for dinner that night.  Went pretty nicely with a Shipyard Summer Ale.  I liked this place because it was casual and right on the water.  We ate on the back patio before heading next door to the Portland Lobster Company for some live music and more beers.

Gilbert's Chowder House

Spread was our last stop on Tuesday night.  We had passed it on Monday and thought it looked neat.  The restaurant itself seemed a little big and upscale, but their interesting drinks were enough to catch our attention.  My drink of choice was gin with muddled strawberries, bail, fresh lemon sour, and a balsamic vinegar reduction.  And Tim got some crazy blood orange tequila drink with jalapeno.


Federal Jacks
One of my favorite stops of the week was Federal Jacks Restaurant & Brewpub.  On Wednesday we took a day trip to Kennebunkport, and while we really wanted to check out Earth, we just weren’t appropriately dressed for something like that.  We loved “Feds” because it had the prettiest view, the most amazing beer EVERRRR (Shipyard Sunfish Wheat), and really good food.  I ordered the blackened haddock tacos after splitting mussels with Tim.  Apparently this place turns into a dance scene with a DJ, but we headed out before it got like that.

Federal Jack'sFederal Jack's

Peak’s Island House
On Thursday we took the ferry over to Peak’s Island, and after walking around we stopped at Peak’s Island House to eat.  This restaurant had a beautiful view of Portland from across Casco Bay, and I had a yummy lobster salad for lunch.  Aside from the lobster salad, I was surprised at the lack of seafood options on the menu.

Peaks Island House

Fore Street
Our dinner at Fore Street was by far our favorite meal of the week, which didn’t surprise me because six different people recommended it to us.  It doesn’t look like much on the outside, but don’t let that fool you!  We loved that the menu changes every single day there.  I ordered flounder with greens over a tomato and mushroom sauce.  Tim ordered roasted duck with risotto.  And we split a side of heirloom tomatoes.  Everything tasted so fresh!  This was a top-notch dining experience.

Fore Street

The North Point
Another week favorite of ours was the bar we went to after Fore Street on Thursday, The North Point.  Although we had really good cocktails at Sonny’s and at Spread as I mentioned above, this was my favorite cocktail place of the three.  It was smaller and cozier inside, and the staff were super friendly.  I think it still had an “upscale” feel, but without seeming “la dee da” like at Spread.  They had a pretty big wine list and ten beers on tap, but I went a little martini crazy this night.  Cucumber and peach martinis for me!

Cucumber Martini

The Front Room
When we woke Friday morning, it was raining and I had a headache from my martinis the night before, so our Greek yogurt wasn’t going to cut it for breakfast that day.  We met a couple earlier in the week who recommended The Front Room (sister restaurant to The Grill Room) for its brunch menu, so we decided to check it out.  We had to wait a long time, but that didn’t matter much to us.  I ordered three items off the sides menu – a fruit bowl, whole wheat toast, and 2 eggs over easy.  Tim’s breakfast was eggs benedict, but instead of over an English muffin it was over gnocchi, and instead of ham it had thick cut bacon.  His was more exciting than mine, but at the time, mine was exactly what I wanted.

The Front Room Restaurant & Bar

While I definitely don’t recommend DiMillo’s for food (we had eaten there a few years ago for my birthday and were not wowed), Dimillo’s is a Portland experience because it’s a big floating restaurant in the middle of the seaport.  On Friday we went there for a drink to enjoy the weather before lobstering.


Portland Lobster Company
Another really fun dinner we had was after our lobstering excursion on Friday evening.  After lobstering for a couple of hours in Casco Bay, you could buy the lobsters for $5 each and carry them over to the Portland Lobster Company where they would cook them (and offer with corn, salad, etc.) for just an extra $10.  We thought this was so fun and so cool!  We hung out at Portland Lobster Company a couple of times during the week because they had live music, fun local beers, and were also located right on the water.

Lobsters after lobstering Portland Lobster Company

Novare Res Bier Cafe
I keep saying every restaurant was our favorite, and bloggers saying everything is their favorite is a pet peeve of mine), but Novare Res was honestly another favorite!  So I’m saying it!  This place was somewhat hidden, but has a HUGE back patio with tons of outdoor seating, cornhole and outdoor darts games, and over 100 beers to choose from.  Beer lovers, a must visit if you are in Portland!

Novare Res

Billy’s Chowder House
For our last day, we headed to Wells Beach, so before heading home we were on the hunt for one last seafood meal.  We thought we picked a decent choice with Billy’s Chowder House, but unfortunately, this was my least favorite meal of the week.  The chowder was very good (thinner than most chowder I usually eat, but the chunks of clam in there were unreal), but my scallops were so disappointing.  Which is ironic since the menu told me they would not disappoint.  They were under-seasoned and my fresh veggie side was a bowl of super buttery corn.  Totally not the way I wanted to end our trip, but I guess one food disappointment isn’t too shabby.

Billy's Chowder House

Although it probably seems like going out to bars and restaurants was all we did, it’s not!  We had a ton of other fun day trip activities that I’ll recap soon, and we did come prepared with other food as well.  We had most of our breakfasts packed and several options for lunch on the days we didn’t go out to lunch.  We brought along cold cuts and bread for beach sandwiches, and I also brought along a big batch of my favorite cucumber salad.  Half the reason we love the Residence Inn so much is for the full kitchen in the room.  Other things we brought along ahead of time included almond flour chocolate chip cookies, almond flour banana muffins, carrots and hummus, Clif bars, cashews, peanuts, crackers, and lots of fruit – bananas, strawberries, plums, and nectarines.  Doing this helped us stay on track when we weren’t splurging, but it also saved us some money!

Packed Food

Unpictured in this post are Gritty’s Brewpub (Tim’s favorite!) and Sebago Brewing Company.  Gritty’s for beers and live music after Kennebunkport, and Sebago for late night food on our last night.  Whoops!

Have you been to any of the restaurants I mentioned above?  What Maine favorites did I miss that I’ll have to check out next time?

Hope everyone’s Sunday is winding down nicely!