In June of 2018, after discovering my friend Amber had never been to Chicago, I put together the most touristy itinerary possible to introduce her to my FAVORITE major city! What turned out to be an extremely HOT (temps in the 90s…help me, this Northerner is melting) weekend also proved to be very fun. Whether you’ve been to Chicago a zillion times [like me] or are seeing it for the first time [like Amber], making all the tourist stops never disappoints. Join us on our trip through the Windy City and discover some of the can’t miss places this city has to offer!
Day 1:
Getting there & around
As a Northern Illinoisan, the easiest way for me to get into the heart of Chicago is by train. I drive into the suburbs (or find a ride, depending on how long I’ll be away due to parking regulations), get on the North Western Metra train and go all the way to Ogilvie Station located downtown. From there I get an Uber or Lyft to get wherever I’m heading. If you’re flying into Chicago, there are tons of shuttles that can take you to your hotel OR you can use Uber/Lyft to go anywhere. I then continue using Uber/Lyft to get around during my stay instead of using an actual cab. Or I hoof it with my own two feet. Pack good walking shoes. The public train system is not very hard to navigate either if you’re interested –> check out the L train info here but that is not my style. Bottom line: you DO NOT want a car when you’re visiting this city–parking is outrageously expensive and hard to find. It is honestly so not worth the hassle and cost!
Where are we staying?
Although I almost always try to stay at Air BnBs when I travel, for this trip we stayed at a hotel Amber booked called The Inn of Chicago. This hotel was AWESOME! There was a beautiful rooftop area where we spent a little time hanging out and reading in the shade one particularly stifling afternoon; the place was much more than we needed but felt very luxurious at a feasible rate. There are tons of incredible hotels in Chicago depending on how much you want to spend and exactly what you want to be close to; a simple Google search will reward you with TONS of choices so just weigh out what is important to you and make your choice accordingly.
What’s on the agenda?
After arriving in the early afternoon and checking into our hotel, we took a walk to our first Chicago staple: Navy Pier! This is a fun [albeit super touristy] area right on Lake Michigan where you can get some good food, have a drink or two and do some shopping! After our trip into the city we were STARVING! Dinner needed to happen soon. Even though it is a chain, it’s one of my favorite places I ate at as a child so dinner was at Bubba Gump Shrimp, famously known from the movie Forrest Gump.
With our bellies full, the next stop was a speedboat tour on the lake that not only goes exhilaratingly fast, it is also has some great information about Chicago’s architecture and history. This is a tour I’ve gone on through Seadog Chicago twice and it has been well worth the money each time [around $41 each]. Make reservations in advance!
We kept the fun going at Navy Pier and walked all around after our boat tour stopping at a bunch of stores to pick up some Cubs gear. We made sure to do a spin on the famous Centennial Ferris Wheel and got some great photos in the process! The ride is a little costly and a total tourist trap but I personally think it is worth the money for special occasions [about $18]!
Our original plan was to go have drinks on the 96th floor of the John Hancock Center [or whatever it’s called now…also still calling the Willis Tower the Sears Tower] at The Signature Room. This is a very fancy establishment complete with a dress code and a definite need for reservations. This location offers gorgeous city views without needing a ticket like you do to access other top floor lookouts. Luckily, in addition to the dining room, a more low-key lounge area where you can pop in for drinks an an appetizer [without a reservation but dressed nicely] is available. We veered off the itinerary and opted for a much more low key evening instead, although I would highly recommend checking out The Signature Room!
Instead of being fancy, we stayed at Navy Pier even longer! After snacking on some churros at a stand on the pier, we found some lounging chairs to hang out in. Throughout the summer, several nights each week, there is an elaborate fireworks show around 9pm. The night we were there we got to enjoy live music, cold beer and a gorgeous show over the lake. It was so relaxing and fun to just sit around and take in the view with the stunning city skyline behind us. Afterwards, we walked back to the hotel and called it a night.
If hitting the hay early isn’t your thing, check out a ridiculously fun dueling piano bar called Howl at the Moon!
Day 2
What’s on the agenda?
We started our day off by walking to a nearby breakfast place with glowing reviews called Yolk where we fueled up with yummy food since we planned to do a LOT of walking that day! This morning we were planning to tackle the Magnificent Mile! We stopped into all kinds of stores including the famous Garrett’s Popcorn. If you haven’t tried this popcorn, you need to go here, order yourself a Chicago mix [caramel popcorn and cheesy popcorn mixed] and realize how much you’ve been missing out. This stuff is magical.
A walk through Chicago is never complete without stopping at Millennium Park for a photo shoot with “The Bean”! This is hands down the #1 most popular picture I see when people visit Chicago so we absolutely could not miss the opportunity. This park is beautiful and hosts ice skating during the winter as well as many concerts during the nicer months. It is a must stop!
After walking all over town, we decided to check out another newly famous stop: Eataly Chicago. This is the coolest multi-level establishment where you can grocery shop for every single kind of Italian cuisine you could possibly imagine, eat at their many small restaurants [where I experienced the most amazing bruschetta of my life!!], drink all kinds of Italian vino, or even take a cooking class. We spent hours here and then grabbed some gelato on the way out!
As with most itineraries I come up with, there was too much to do on this day and we ended up not doing 2 super fun options that are SO CHICAGO it hurts.
1. Goose Island Brewery— if beer is your thing [and even if it’s not], this is one Chicago classic that you should absolutely work into your visit!
2. Oak Street Beach— it’s kind of crowded sometimes and it’s hard to find a bathroom and it’s a pain in the ass to get to with all your beach gear and the water is freezing ass cold year round and there’s no alcohol allowed BUT, somehow, it’s actually a really fun afternoon venue [especially for a bachelorette party which is exactly where we went when my bestie Amanda got married!]
For our night activity we went to dinner at The Vig [very close to our final destination] where we had a couple appetizers followed by my #1 most favorite thing to do while in Chicago — a comedy show at The Second City!! This is a stand up comedy/improve group that performs at a small venue on North Wells. For this trip we saw a show called “Dream Freaks Fall From Space” and it did not disappoint. We even had front row seats!! I have been here many times and it is always such a good show and for a great price [tickets around $36 with a 2 drink minimum]. I highly, highly recommend getting there [and getting there early…it is a first come, first serve seating situation]!
Day 3
What’s on the agenda?
Day 3 started with a highly recommended breakfast at Batter and Berries where we waited a reeeeally long time to get into quaint, adorable restaurant specializing in french toast. I opted for a sample platter of different flavors of french toast and it was worth the wait! They do not take reservations so the earlier you get there, the better.
Our plan after this was to walk through a Chicago favorite — the Lincoln Park Zoo with a stop at the Alfred Caldwell Lily Pool north of the zoo. However, it was so incredibly hot outside already, we figured most of the animals would be seeking shelter in their exhibits. We also knew with what we had planned for the afternoon, the sun may get the better of both of us! The zoo is free and a great place to take a stroll. The lily pool is a breath-taking gem hidden in the city as part of the Lincoln Park Conservancy. It is definitely a hidden oasis.
After taking a short nap and lounging on the hotel roof to read for a bit, we put on all of our Chicago Cubs gear and headed towards the historic Wrigley Field for a very hot afternoon game! We sat in the bleachers to get the true experience of a Cubs game and pretty much roasted the entire time [I drank 6 beers…did not urinate once. Hello, dehydration.]. We had absolutely no complaints about this and had a great time cheering and people watching! Plus Amber got to check eating a hot dog and drinking a cold beer in the bleachers at a Cubs game off her bucket list!
After the game, the crowds were thick and transportation back to our hotel was proving to be difficult. Since both of us are huge Iowa Hawkeye fans, we found our way to Merkle’s Bar and Grill, the Iowa Hawkeye bar in the middle of Wrigleyville! We had a couple drinks, waited for the crowds to die down and then made our way back towards our hotel.
That night by dinner time we were exhausted so opted for carry out from the one place you HAVE to go for Chicago pizza: Gino’s East! We got carry out, ate way too much in our air-conditioned hotel room, and promptly passed out. It was a gloriously “Chicago” ending to a great weekend in the Windy City!!
Chicago remains my favorite big city not only because I’m a Northern Illinois girl and former student of DePaul University, but because of all Chicago truly has to offer. There is so much diversity, history and opportunities to explore the world without even needing to leave Chicago. The amazing restaurants to eat at are endless; you could live here for 50 years and still not get to all of them. Do some of your own research and look around — there is something in this city for absolutely everyone!
Happy travels <3