If you follow along on Instagram you probably know I arrived back from a 14 day adventure down the West Coast. My mom and sister were with me and I met up with some friends on the last weekend. But before the adventure began, I had a work trip to attend in Chicago while my mom and sister were living it up in Idaho! Seriously, they were – huckleberry vodka was involved! Thankfully, my bestie Julia was able to tag along and honestly it was one of the best parts of the trip! So here is your non-touristy Chicago travel guide!
If you are a small town girl like me you probably have a similar outlook on cities. Too much cement, always surprisingly cold, lots of walking, getting lost, and shopping options that will make you blow your entire trip budget immediately! I had visited Chicago before and done most of the touristy stuff and Julia was down for whatever so we went in with no plan! So here is a guide ranked from super relaxing to not so relaxing for fun exciting things to do in Chicago!
#1 Treat Yo’Self (Super Relaxing)
Since I was going to the beach after Chicago my nails were in dire need of a touch up. Julia and I had already planned to go to get mani pedi’s prior to the trip and found a great little spot called Spa O Club just a block away from our hotel. They had a early bird special of a mani & pedi for only $40 – such a deal!
Another budget friendly pampering option: blowouts! When I was in Nashville last year I got my first blowout and swore it would be on my to do list for every trip going forward. On the last day I was a bit of a hot mess – my meetings got done early and I had 2 hours to kill before leaving for the airport. I ended up trucking my suitcase and two carry on’s to three, count em’ THREE different blowout salons until they could fit me in. Most were booked up so no ill will on the salons since I was last minute. But through my trek I did get a peek into a few of them and would only recommend 2 out of the three.
The first that I went to was Blowtique – I would give it a 2.5 out of 5 stars for the salon decor and service. The girls working weren’t the most welcoming did have that fancy wow factor.
The second one was Blowout Junkie which I would recommend. It was pretty busy and the decor and salon were very clean and cute. 4 out of 5 stars.
I finally got in at Drybar in River North – was it the best blowout I have ever received? No. But it did the job, and it was probably the cutest and most organized out of all of them. 4.5 out of 5 stars!
#2 Brunch (Pretty Dang Relaxing)
Brunch obviously trumps cocktails in the relaxing categories because it means you don’t have to go to work that day! We grabbed brunch on Sunday at Homeslice (thanks for the recommendation Taylor!) They had awesome breakfasat sliders and a Hangover Iced Coffee that was seriously the bomb (officially requesting that JR make me this every Saturday morning). After Homeslice (which is in the super cute Lincoln Park neighborhood) we stopped into Alice + Wonder for some quick shopping. This boutique is at a great price point and has some awesome stuff! Other brunch recommendations from friends were Zella, Fremont, and Summerhouse.
#3 Cocktails (Always Relaxing)
After attending meetings all day cocktails were on the menu for the evening. My favorite place in Chicago was Three Dots and A Dash. I have always been really into anything tiki/Hawaii/surfing related after all the Soul Surfer and Johnny Tsunami viewing as a child so Three Dots and A Dash was definitely my vibe. *I also feel like now is a good time to note that I cannot swim. Like at all.*
This bar is located in an alley with only two tiki torches to denote it’s entrance. We arrived 20 minutes after they opened and had to sit at the bar since they were already full. The drinks and the food were amazing!! If you are planning ahead with a group I would definitely make a reservation and order one of the giant group cocktails!
We also went to Federales for dinner one night and the food and drinks were awesome! They also have this tequila shot in an ice shot glass where you take the shot then throw the glass at a bell – super fun party trick! I would also recommend this place for a group. There is also an avocado wall mural and another wall mural right near by we didn’t get a picture in front of so be sure to stay on the lookout for a fun photo op! Other recommendations were Tuco and Blondie, Park and Field, and Happy Camper!
#4 Relaxing-ish Touristy Things
The meeting I attend annually is always located right on the Magnificent Mile so it’s really easy to take a stroll and check out all the stores. Our hotel was right across the street from Zara (my fave!) and Dylan’s Candy Bar is always a fun one if you’ve never been.
We also met up with our friend, Bridget, who lives in Chicago and visited the Art Institute of Chicago and Buckingham Fountain. After, we crossed Lake Shore Drive near the fountain and sat by the lake for an hour or so – super relaxing. Then we went to dinner at Vapiano – this is seriously my families favorite! They go every time they are in Washington DC and it is SO good!
On the last night Julia and I were wandering around the River North area and decided to do a Wendella Boat Cruise. If you are into history and want to get out onto Lake Michigan I would recommend this one. If you are looking for a good architectural tour I would do this one – JR and I did it the first time we visited and I was surprised how many facts I retained from 2 years ago!
#5 Touristy Dining (not as relaxing as regular dining)
JR and I visited for like 3 hours one time before a layover and went to Giordano’s and the second time we visited we went to Lou Malnati’s. One claims to be the “most famous” while the other claims to be the “absolute best” in the deep dish category. There are probably seven billion other “best Chicago deep dish” places so you really can’t go wrong. We didn’t get any pizza while on this last trip but a friend did recommend Chicago Pizza and Oven Grinder Co. She did said it had a super long wait time – as do most of these places – so be prepared!
#6 Full On Fanny Pack Tourist (Get your walking shoes on!)
If you have never been to Chicago then you are probably going to want to see all the big tourist sites. The Bean is at the top of the list – did your really even visit Chicago if you didn’t see the Bean?
I didn’t particularly love the Field Museum but it may be your thing. It features the most complete T-Rex ever found and right now they have a Jurassic Park exhibit.
The Willis Tower (with the glass floor skydeck) is fun but be prepared to wait in line and go on the least cloudy day.
I would also try and hit up Wrigleyville. I read that they give full tours of Wrigley Stadium if the Cubs aren’t in town.
#7 The Most Stressful Place To Visit in Chicago
If you know anything about me you know that I have been OBSESSED with dolphins, orcas, and any other kind of whale since I was a kid. JR and I visited the Shedd Aquarium two years ago, unknowingly aware that captive wild-caught cetaceans were held there. The beluga whales were taken from their home in the Arctic Ocean near Russia and the pacific white sided dolphins were captured in 1993 near Catalina Island, California. I could go on and on but this is just my mini PSA to be very aware of what you are funding when you visit the Shedd Aquarium, SeaWorld, or even going to swim with dolphins on vacation in Mexico. These animals are highly social and naturally live in a pretty large place (i.e. the ocean). Any effort to stop funding these facilities helps us get closer to all cetaceans being able to enjoy a life in the wild.
I’ll keep from ending on such a downer! Here is a fun GIF of us drinking beer out of straw on our boat tour! Once we got out on the lake we were not going to take any risks!