katie
- Sep 13, 2019
- 5 min read

Three nights in Chicago

The whole family met in Chicago to celebrate my cousin’s wedding. A lot of drinks, a little sightseeing, and a lot of laughs in a great city.

A wedding is a great opportunity to travel to a place you might not have went otherwise. Don’t get me wrong, I LOVE Chicago, but seeing as I live in another big city, I generally try to avoid traveling to other big cities. However, the June weather and cousins in top form provided a great landscape for a weekend in Chi town.

Here are my best tips for a weekend that is fairly balanced in the cultural, debaucherous, and enjoyment level. Keep in mind we were having to deal with 15 peoples opinions and didn’t get to have dinner two nights because of the wedding.

Lodging

This trip we stayed at the Intercontinental Magnificent Mile, quite honestly because that’s where the wedding was. I give it a 7/10. Nothing is wrong with it per se, but it felt like a business meeting hotel and I could hear the conversations in the rooms around me. And the A/C simply wasn’t up to par. Previously we have stayed at Hyatt Regency (I wouldn’t again unless I had to) and the London House. I loved London House- it felt clean, modern, and the views were insane! Next time I think we would opt for a hotel in the Gold Coast like the Thompson Hotel. I was especially annoyed with Intercontinental because I got zero points for my stay and would have rather stayed at SPG/Marriott/Bonvoy hotels if I’m going to go with a big chain. Cie la vie.

Drink

Chicago’s Riverwalk offers something that most cities don’t- relaxed drink options directly on a river. The riverwalk is packed with great options. My favorite is City Winery, where you can perch up close to the water and settle in for a nice view of the city and people. Also on the river walk, is
Broken Shaker at the Freehand has beautifully mixed drinks in a fun environment. Music and fun, without pretension or club vibe. We had a group on a Thursday night found a great seat, where the people sitting next to us were from the same part of California we are from! Small world!
Rooftop at the London House Yes, yes, I’m aware that there’s probably more cultured places that aren’t so touristy. But I like a glass of rosé and a view and there aren’t many views better than this one. My advice- go early (pre 2pm). We had no line, could enjoy the views and had our own little corner to ourselves. Secret tip- when the bar upstairs is taking too long for drinks, one floor down to the bar (same level at restrooms), order there and take back up. That’s probably not what they want you to do, but hey, saved time and aggravation. My best pics and probably funnest two hours of my trip was laughing and having drinks at the top of London House.
Eataly is not native to Chicago, but when all the boys wanted to go drink some IPAs, the girls went to go have a charcuterie platter and some aperol spritzes at Eataly. This one is not as big as NYCs Eataly, but the set up is cute and great for drinks if you’re in the area.

Other fun places:

Culture

Some of our family went all-in on activities and culture on this trip. I have been to Chitown before and took a more relaxed approach. This trip I went to two places: the Chicago Cultural Center and the Art Institute. The architecture and Tiffany glass ceilings in the cultural center are not to be missed. We took my 86- year old Grandma to the Art Institute so she could see some Degas, Manet, and Monet. The art collections were impressive. I’m not someone who spends more than an hour or two at an art museum, so it was easy enough to move around and find the art we wanted while also creating some beautiful memories with Grandma.

Also to check out: Science Center, Millennium Park, Pilsen graffiti walls. Everyone raved so much about the Science Center and will be top of my list next time I’m in Chicago. We gave the Willis Tower a pass after last time we had tickets and there was still a two hour line. No thanks. We have been in enough tall buildings.

Fun

I always recommend going to a Cubs game because quite honestly there are very few places that are left like Wrigley Field. I also went to a Jesuit University and I remember the priest giving a really quick homily one day at mass saying 'be loyal to God, like Cubs fans are loyal to the Cubs'. So there's something there!

We weren't able to go rent a duffy boat last time I went to Chicago because there were thunderstorms. I do love the Architectural Tour, but taking a boat out on the Chicago River is great.

Eats

Some other places we tried: Frontera Grill by Rick Bayless. Love Mexican and Rick Bayless is one of the best Mexican chefs in the country. We had a lovely brunch at Somerset in Gold Coast and everything our avocado-toast, bloody mary drinking hearts wanted.

s.k.y., the first restaurant by chef Stephen Gillanders is something not to be missed. It's true that the chef/owner's sister and I were roommates in college, but that's not why I like s.k.y. Stephen is beyond talented and worked under Jean Georges for many years. His food is elegant, but not stuffy, inventive, but comforting and worth the uber to Pilsen. S.k.y. has been listed on many of the top lists in the country.

I've never been to Aviary, but of course is on the list as it's a bucket list and a Grant Achatz is a master!

Beauty

As a rule, a blow out is a must for a wedding, so I went to my tried and true, DryBar in River North. Unfortunately we didn't know that this particular location does not have prosecco like the rest of the locations (it's across from a school), but does offer BYOB. So, we imbibed down the road afterwards. A good blowout, but honestly, a lot longer of a line that at most of the other locations.

And Ezza Nails- one of the best nail experiences I've ever had. Next time I travel to Chicago, I'll honestly go with chipped nails just so I can go have my nails done again at Ezza Nails. It was modern, organized, professional, so clean... and usually I downplay my millennial-ness, but this was millennial done right, and better than any other nail salon. If you're near Magnificent Mile, go!