A Trip to Chicago, IL

We recently returned from a week in the Midwest visiting Luke’s parents. We spent most of our time in Chicago showing my dad around as this was his first time here. This trip looked A LOT different from past trips due to COVID-19. For weeks and weeks leading up to the trip we were unsure if it was even going to happen. We even second guessed the trip many times. Our flights were changed numerous times as the airline consolidated flights for the week. I was scared to even get on an airplane during a pandemic! When we finally decided to go ahead with it, we had a lot of conversations on how to proceed with our travel plans as safely as possible. Chicago was in Phase 4 of re-opening and we had a game plan. We brought plenty of face masks, disinfectant wipes and hand sanitizer. We planned activities where we could maintain distance from others and also planned on only dining at establishments that had outdoor seating. I was quite impressed with how safe I felt in Chicago. Most places we visited had temperature checks and everyone had social distancing in place. By the end of the trip it felt like my face mask was a permanent fixture to my face – a small price to pay for safety though.

While it wasn’t’t the trip we had initially planned on, it ended up being a great time with family and I’m grateful we were able to make it happen. We had non-stop flights on Alaska Airlines and they kept all middle seats open. They thoroughly cleaned everything and scaled back their in-flight meal service to only offer bottled water, a few sodas and snack packets. Face masks were required by everyone – which quite honestly felt safer than visiting Safeway or Fred Meyer down the street from my house where half the shoppers don’t even bother with them. While I understand traveling is controversial right now, I feel good about how we handled everything and the safety precautions that we took. The number one reason for this trip was to see family that live outside of Chicago and since it is summer, we spent time in the city together.

Where we ate:

Ersi Brewery (This was our first dinner after landing at O’hare. The weather was perfect, the patio was spacious and the food and beers were just what we needed after a day of traveling.)
Piece Brewery and Pizzeria (A great spot for pizza and beers in Wicker Park)
King Crab House (What a gem! We were walking around Lincoln Park and spotted this cute place in the neighborhood. I put my name on the list for dinner and even got to pick out where we wanted to sit on their patio.)
Kaiser Tiger (A fun spot with plenty of outdoor seating)
Kennedy Rooftop (This was our last dinner of the trip. Their patio had just recently opened and we snagged the best table there was – unobstructed views of the entire Chicago skyline!)

Other places that we love in Chicago: Velvet Taco, Le Colonial, The Publican, Giordano’s, Public House, Cindy’s Rooftop, Eastman Egg Company, Gaslight Coffee Roasters

Places that are on our list for our next visit: The Purple Pig, Girl & The Goat, Au Cheval

Where we drank:

Paradise Park (A fun spot with a huge patio to grab a few drinks)
Island Party Hut (After a boat tour on the lake we stopped here for a few beers. They have an expansive outdoor area and we found large bench to sit on right by the river.)
Big Star (We stopped in here or a few margaritas to get out of the sun)
Pilot Project (Creative and delicious beers in a beautiful outdoor space)
Sully’s House (We came across this place on the way to another place. When that other place didn’t work out, Sully’s welcomed us with open arms – and a very socially distant patio.)
Murphy’s Bleachers (We originally booked this trip before the pandemic, so we planned on catching a Cubs game on the trip. While the Cubs game didn’t happen, we walked around the outside of the ballpark and stopped in here for lunch and beers.)


A lot of walking (We walked all through Lincoln Park taking in the sights of the city and the tree-lined neighborhood streets, Millennium Park, Wrigleyville and Wicker Park.)

Boat Tour (Wendella boat tours now require masks to be worn at all time and they’ve also restricted the number of passengers to allow for social distancing)

A Trip to Chicago, IL

We just got home from a week in the Midwest, and man was it hard to come home after this trip. See, I’m sure that summer has arrived everywhere in the US, except for Portland, so it was exceptionally nice to bask in a week of sunshine. The trip was filled with food, family and friends, all of my favorite things 🙂 We spent the first few days of our trip in Chicago, then we visited Luke’s parents in Indiana and our good friends down in Indianapolis. We even snuck in a day trip to Luke’s college town in the southern part of the state (more on that later!). Here’s a list with links of our Chicago activities: what we did, what we saw and what we ate…

We started off the trip with a quick dinner and beers at Public House while we watched the Cubs game. Then we made a visit to the Raised Rooftop Bar (where Heather met up with us!). It was such a good way to kick off the trip. The sun was shining, the beers were flowing, so you know the Copeland’s where having a great time! Our second day included morning coffee and brunch at The Publican. It was hard to choose what to order because I wanted everything on the menu! I decided on wine poached eggs and they didn’t disappoint.

(Scroll down to see more!

We took a boat cruise on the Chicago River and out on Lake Michigan. This is the third time I’ve done a boat tour in Chicago – so obviously I would recommend this 🙂 It’s such a great way to see the city from many different points of view. We’ve always used Wendella Boats and love them! Plus they have a bar on the first level 🙂
FUN FACT: Luke proposed to me in front of the Water Tower Building five years ago, so this spot will always hold a special place in my heart. 
One morning we ate a quick breakfast at the Eastman Egg Company. This place started out as a food truck and partners with local farms – it was such a fun and delicious little spot. I got the biscuit with ham, egg and house made blackberry jam.
We spent a morning walking around a few Chicago neighborhoods. We picked Lincoln Park and Bucktown to explore. They were both adorable and I felt like I could possibly live there.
Luke’s breakfast bowl below came from Gaslight Coffee Roasters, which was another amazing spot. Luke always finds the best spots by the way. We were staying in Logan Square and Gaslight was a short walk from the AirBnb. We also had iced chai’s that were fantastic!
Can you go to Chicago in the summer and not take in a Cubs game?!? Of course not! Luke’s parents drove over from Indiana and we had an early dinner in Wrigleyville before the game. Luke was happy because they won and we sang along to Go Cubs Go (and by the way… I was just getting this song out of my head after last October…).
You can’t leave Chicago without indulging in a Chicago Dog! I picked this one up from a street vendor in Millennium Park.
We visited a few other places that I didn’t take photos of (how dare I!). We had a delicious dinner at Velvet Taco on Rush Street. Those tacos were seriously sooooo good. We also visited Cindy’s Rooftop and had a biiiiit of a wait to get up there – unfortunately it wasn’t my favorite place as we encountered some less than pleasant people there. Plus, it was so crowded that it was somewhat unenjoyable.
Overall, the trip was just fantastic. My sister joined for the first few days and it was so fun showing her the city. Next time I won’t let five years pass in between trips!
– Photos © Holly Copeland –

The Robie House

While we were in Chicago last month, Luke’s parents made an extra stop near Hyde Park just for me. We stopped at Frank Lloyd Wrights Robie House. Although I didn’t go in for a tour, I was just as content walking around the property and snapping photos of this gorgeous house. Back in college while I was studying Art History, I fell in love with Frank Lloyd Wright houses, especially this one, so it was so great to finally see it in person.
– Photos © Holly Carman –

Chicago, from the top

While we were in Chicago we went to the top of the WIllis Tower (formerly Sears Tower). It was such a beautiful and clear day – the views were amazing. It’s kind of pricey to get up there, but once you’re there it’s worth it. At 1300+ feet up in the air, you can step out into a glass box that extends off the skyscraper and look to the city below you. It’s a crazy experience, but lots of fun.
– Photos © Holly Carman –

Our Big News!!

If you’re friends with me on Facebook, or follow me on Instagram, then you probably already know our exciting news. If not, here it is… Luke proposed to me in Chicago! We’re over the moon excited! I couldn’t be happier with how everything happened and can’t believe that I’m now engaged to my best friend.

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It was Tuesday afternoon and I was heading back from work in the suburbs. I had to drop off my rental car at the airport and then hop on the orange line train back downtown to our hotel, where I was meeting Luke (who had just arrived about an hour earlier). We decided to go out for a few drinks since it was pretty early (4pm early). We went to the Wit Hotel, just around the corner and had a few drinks at their Rooftop bar before we got ready for our dinner reservations.

Beforehand, Luke had done some research and found Le Colonial, a French/Vietnamese restaurant on Rush street, that he knew I’d just love. After a short cab ride, we arrived at the restaurant and proceeded upstairs to the bar because we were kinda early. While up at the bar we casually chatted and I just remember being so happy that Luke was finally in Chicago with me. I could tell Luke was even more excited than me, because Chicago is HIS city.

We had the best time at dinner and our restaurant was absolutely amazing. Luke couldn’t have picked out a more perfect place for us. The food was to die for and the atmosphere was so romantic with a south pacific flair. There was soft French music playing in the background as we kept smiling at each other and raving about our food. A sweet couple sitting next to us took our picture and we took theirs as well.

After we left the restaurant we decided that we should go up to the Hancock Tower (just a few blocks away) and have a drink on the 95th floor Signature Room. Before we got there, Luke kept trying to find the Water Tower Building. He kept looking at his phone and trying to figure out where it was… Of course me being oblivious to everything around me, I just thought that he wanted me to see it because it’s a Chicago landmark. We leisurely strolled up to the stairs of the building, hand-in-hand, when Luke stopped me. He turned around and said that he brought me here for a reason. It was right then when I knew what was happening. He was down on one knee and giving me the most beautiful speech that I could have ever imagined. He explained the significance of our location, what it meant to him, what it meant to us… The tears started flowing immediately. I couldn’t believe it was happening. I tried to remember everything he was saying, but it was all a blur. It was such a sweet moment that I wish could’ve lasted forever.

After a lot of hugs and kisses and more crying (happy tears!!) we walked over to the Hancock Tower & rode the elevator up to the Signature Room. Once we got settled in at our table and ordered a few drinks, we called our families and texted a few friends. We kept the celebrating going at a few more bars on Rush Street before we took a cab back to our hotel. I went to bed thinking that was one of the best evenings of my life!

I had always wondered what Luke would do, when the time came that he proposed to me. Nothing I ever imagined came close to how perfect everything was on Tuesday night. The drinks, the dinner, the ring, the guy… that entire night – was the best I could ever ask for. I truly am one lucky girl.

This is where Luke proposed
– Photos © Holly Carman –

Chicago Sunset Cruise

I was sitting in my hotel room on Sunday night at 7 o’clock trying to figure out what to do for the rest of the evening. I was talking to Luke on the phone & he said I should do a sunset boat cruise. I then remembered that I wasn’t too far from the Wendella Boat Tour dock, so I got online, looked up their schedule, bought a ticket & ran out the door to go catch the boat! I arrived all hot & sweaty (ya know, Oregon girl in humidity…) but it was so worth it because once on the boat there was a nice warm breeze & a sunset that was absolutely gorgeous. We cruised around on the water for a few hours taking in the Chicago skyline (& me snapping a million pictures). It was by far one of the best spontaneous adventures I’ve taken 🙂
– Photos © Holly Carman –


I’m in Chicago right now and let me tell ya, it’s hot and humid. The opposite of Portland weather, but I’m loving it. I’m here for work for a few days and then vacationing with Luke and his family for the rest.
When I got to town, I checked into my hotel and then hit the streets with my camera and started snapping away. Chicago is such a beautiful city, it’s hard not to. I grabbed a quick dinner and the walked over to Millennium Park, came back to the hotel for some wine tasting in the lobby and then I headed back out to walk across some bridges and hop on a last minute sunset boat cruise of the city. Whew, that was a lot for just the first day.
I’ll be working all day today and Tuesday so I wanted to get some fun stuff in beforehand. Depending on how much time I have during the week, I might be back to blogging, or I might not. But I promise that I will get around to showing you all some Chicago pix soon.
Have a great week!