As mentioned maybe 15 times already, my Chicago trip was one of my favorite vacations yet. I think some of it might have been due to the fact that Tyler and I had the freedom to kind of just do whatever and go wherever we wanted on the days not set aside for family. Growing up and being the only child, I always had to do what my parents did on vacations. I never had the luxury of venturing off with a sibling or doing fun kid stuff. It was always studying plants in national parks (my dad LOVES looking at rocks and plants), tours, and museums (which are cool now but not so cool when you’re 7-9 years old lol).
Anyway, I’ve compiled a mini “must see” from our trip! I am no Chicago pro by any mean, but being there for 6 days gave us a pretty good feel for the fun and cool spots!
Blog Outline:
1. Hotels (we stayed at 3)
2. Tourist attractions
3. Small bites & specialty drinks
4. Big portion restaurants
HOTELS
We decided to do two nights at each hotel because we wanted to get acquainted with and more familiar with different parts of Chicago. We stayed at the Talbott Hotel in Gold Coast (this area comparable/resembles Manhattan), The Gwen which was by the Riverwalk but slightly inland, and LondonHouse which was ON the riverwalk and by a ton of shopping, although The Gwen and LondonHouse were only a couple blocks from each other. I love all three equally. I loved the location of Talbott. The Gold Coast neighborhood is totally my style. I loved The Gwen for it’s sexy, chic, and luxurious style (and it’s attached to Nordstrom… LOL). I loved the views of LondonHouse and how accessible it was to all the hustle and bustle! For LondonHouse, REQUEST a river view or else it’s not even worth it at that point. We paid an extra $50 for the upgrade! You’ll see below what we woke up to in the morning *heart eyes*.
Talbott Hotel
The Gwen
LondonHouse
The view from our bathroom!
TOURIST ATTRACTIONS
SkyDeck at the Willis Tower
I mean, duh. So touristy but it’s just something you have to do to initiate yourself as having visited Chicago. That and the bean haha! I literally could not look down when getting on the glass, I was mortified, so don’t ask me how the view below was because I have no idea haha. I would suggest going around sunset time! The sun is lower so the lighting and sun placement isn’t as hard!The Bean
Again… just go and get a quick selfie with it. I mean, did you even visit Chicago if you didn’t see the bean?! Touch it, hug it, whatever. Just make sure you sanitize after cause there are a LOT of hand prints and spears all over it. You don’t want to catch the cold or flu!Riverwalk
Just walking around the Hudson was so soothing! Something about being in the middle of a concrete jungle but still inches away from a body of water is so relaxing! Take a water taxi while you’re at it too! Or you can take a boat tour if you’re an info junkie!The Arts Cafe at Restoration Hardware
This can also fall into the next category but for me, it was a must/attraction! There is a cafe at the Restoration Hardware furniture store in Chicago. The interior is truly a dream. I can’t even explain how beautiful it is. It looked amazing in photos but is one of those places that is 10x more amazing in person. We went for brunch Monday morning! Here are some tips when visiting:
1. No reservations. Go as soon as it opens – I suggest arriving 15 minutes before open. There will already be a line forming. We went on a Monday and there were several folks ahead of us
2. It’s pricy-er so expect to pay, it’s no Denny’s Grand Slam prices y’all. I ordered their chai, burrata (BOMB) and egg scramble
3. You can totally roam the store after! The top floor has a very cute rooftop space
4. If you get there later, expect at least a 30 minute wait. Wait can increase up to 2 hours on weekends
5. You can order drinks at their bar and chill on their signature white couches during your waitWrigley Field
If you’re a baseball fan or sports fan, go. Fortunately (because it was still season) but unfortunately (we had to pay post season prices), the Cubs still had a shot at playing at home if they won, so we bought tickets for game 5. Unfortunately, they lost to the Rockies so they were knocked out of post season so we didn’t got to a game. We also couldn’t go inside since they had already begun construction. Fortunately, we got our well spent money back lol! We can always go back for a game, no big. Anyway, you can’t NOT go to Wrigley Field. It’s just iconic, it’s historic. So just go.
SMALL BITES/SPECIALTY DRINKSWe ordered ahi poke, calamari, beef skewers (not shown)
Hampton Social
I saw this place on Instagram so many times and couldn’t NOT go. It’s one of the cutest spots in all of Chicago. They’ve got a full menu of smaller dishes but all sharable and still relatively filling! The space is huge so you should not have too much trouble getting a seat. Word on the street is that Saturday and Sunday’s are poppin. I would love to go back during the summer and hang out on their rooftop patio are! There are two locations. This one is their newer space off Grand and Rush across Nordstrom and The Gwen Hotel.J Parker Rooftop at Lincoln Hotel
If you’re into rooftop bars and amazing views, The J Parker will be your best bet. They’re the only bar in all of Chicago that has a 180 degree unobstructed view of the city, beach, and park. Their drinks are also amazing. There wasn’t one that we didn’t like. They do change their drinks seasonally so I recommend visiting a few times a year! Food wise.. G-R-I-L-L-E-D C-H-E-E-S-E. I am not joking, and neither is Tyler because he is the world’s biggest grilled cheese connoisseur, best grilled cheese ever. I don’t know what about it that makes it so amazing, but you MUST order it. It also has a slight kick to it as well which totally takes it over the top!
The Aviary
My sister-in-law (almost.. one day… really my brother-in-law’s girlfriend lol) suggest this spot to us! It was really hard to take photos because it was so dark inside but HOLY COW. Just look at the photos on their Yelp page. These were easily the coolest drinks I’ve ever had. They came out in copper birds in a glass nest, had michelada popsicle drinks, drinks that came in wheels, drinks with ice cream… name the craziest combo and they will have it on their menu. It’s pricey so you’ll want to get a cheaper dinner before hand but it’s worth visiting. There’s truly no place like it. Also, online reservations are required. You can try to walk-in but 99% of the time, they’ll turn you away. They were fully booked on the Tuesday evening we went!LondonHouse Rooftop Bar
I mean, we stayed at the hotel so why not check out their rooftop bar right? I would say it’s much more rewarding during sunset and in the evening. It’s still beautiful during the day, but with the city lights at night, there’s just nothing that compares.
BIG PORTION RESTURANTS
Lou Malnati’s
I’ve came to realize that Chicago folks (and visitors) are split down the middle between Lou Malnati’s and Giordano’s. Tyler is a Lou Malnati’s fan. I didn’t get to try Giordano’s to form my own opinion but according to our Lyft driver who is originally from Greece but a 30-year Chicagoan, Lou’s ingredients are bought fresh everyday. They don’t buy the full quantity and often have to buy more during opening hours because they want everything to be as fresh as possible throughout the day. Giordano’s does not do that. Again, this is just what our driver said. PERSONALLY, I’m a thin crust girl. One slice of deep dish put me in a food coma so I’m completely indifferent about the topic of comparison!
Harry Caray’s
Harry Caray’s is my new favorite steakhouse of all time. Over Mastros, over Flemming’s, over Ruth’s Chris. If you’re a baseball fan, come visit the restaurant! There’s a lot of history behind Harry Caray. The restaurant location off Dearborn & Kinzie was also Al Capone’s old hide out spot during them mobster times. They have an entire staircase full of original newspaper articles and videos playing that lead to his little hide out cell. I’d be lying if I said I wasn’t a little freaked out seeing it.Cai
Cai is an authentic Chinese restaurant out in Chinatown (about 25 minutes outside of the city). We went here Sunday with my family. My cousin who got married Saturday of our trip also did a traditional Chinese celebratory reception aka 10 courses of Chinese goodness. If you want some good, real Chinese food, you need to com here. It’s one of the best spots in town. It’s also not as MSGed as most Chinese spots are. Usually I’m downing water throughout the courses but I was totally fine which is HUGE plus.
I truly cannot wait to go back to Chicago! Tyler RAVED about it for months leading up to and I can 100% now relate. I love a lot of different states like Arizona and Colorado, but not once have I been so quick to say, “I could totally move and live here”. We may look into moving here or getting a timeshare whenever Tyler retires haha.