Last month I spent 1 week in Chicago. At the start of 2018, I made a list of U.S. cities that I wanted to see again, and Chicago was probably the one I was most determined to actually revisit this year. I tried to go earlier in the year, but I kept putting it off. Next thing I knew, summer was almost over and I knew the weather would only be on my side for a little bit longer.
So I bought a cheap bus ticket ($6 each way!), booked a bed in a hostel, and started putting together a list of all the places I wanted to go. 1 week in Chicago might sound like a lot to the average traveler, but I like to take my time. Plus, traveling for me as a travel blogger is a little different. I spend a lot of time working on content, taking photos, doing research and taking notes, so that I can share the best places with you guys. I don’t like to create guides based on just 2 days in a city, because that doesn’t really leave you with the best recommendations.
My main focus for this trip was coffee, so I did my research and made a map of all the best coffee shops in the city. Of course, the list was too long to actually try them all (I tried really hard, drinking 2-3 coffees a day). But I put together a list of the best coffee shops in downtown Chicago so that I could still share my favorites within one small area of the city. Now I have an excuse to go back again so that I can finish my coffee to-do list!
But I did more than just drink coffee while I was in Chicago. I also did a lot of walking, visited a few museums and attractions, tried to eat at as many vegan/vegetarian restaurants as I could, and generally tried to get a feel for the city. Now that I have a general idea of what Chicago is like, I can make a better plan for my next visit and start seeing more of the other neighborhoods. I also spent a good portion of my time working, so having a full week in Chicago ended up being a good balance.
I don’t post photo diaries or travel journals here like I used to, simply because they aren’t necessarily “helpful” for people planning a trip. But I want to try something a little different with this post and see what you guys think.
I documented my week in Chicago on Instagram Stories, as I try to go with all of my trips now. I think it’s the best way to take you guys along with me, so that you can see my trip in real time. I thought it would be fun to share my Insta Stories here as my Chicago Travel Diary. That way you can see exactly how I spent 1 week in Chicago, where I went, what I ate, and just generally see the city through my eyes.
I’m including lots of info along with my story slides so you guys can actually use this to plan your own trip too. And if you like this post, I can make this into a series and start doing these for every trip. Of course, you can always see more stories and photos from my travels by following me on Instagram (@TravelDazeco), but it’s easy to miss that stuff on social media sometimes.
This isn’t exactly a 1 week in Chicago itinerary, but I’m going to share as much of my trip as possible in one simple post. Consider this a more personal travel diary, rather than a guide.
1 Week in Chicago Travel Diary
Chicago – Day 1
I arrived in Chicago late in the evening. I took a 6 hour bus ride to get there from St. Louis, and it was running late. It was dark and pouring rain when I got there, so I got an Uber. It wasn’t until the next morning that I got a real glimpse of the city through my hostel window.
Stay: HI Chicago Hostel
Address: 24 East Congress Parkway
Coffee was the number one thing on my mind, so as soon I woke up, I walked a couple blocks to try Hero Coffee Bar. I asked the barista for a drink recommendation, and I ended up with a Basil Orange Latte. It was so good, way better than expected since I’m not a huge fan of basil.
Hero Coffee Bar
Address: 439 South Dearborn Street
After that I made my way over to Revival Food Hall. This is an “upscale” food court kind of place, with local food vendors and lots of seating (plus free wi-fi). I started with a chai latte from Revival Cafe, and then moved on to a smoothie bowl from Graze for breakfast. I spent a bit of time here to stay out of the rain, and did a bit of “planning” for the rest of my day.
Address: 125 south Clark Street
The rain cleared up so I took a walk through Millennium Park. I could hear music playing as I walked along Michigan Ave, so I slowly moved towards it. It turns out the Grant Park Symphony was rehearsing in the Jay Pritzker Pavilion, so I just stood and watched them play for half an hour. It was such a nice surprise and a lovely way to spend some time. They perform here (for free) all throughout the summer months, so just stop by the pavilion while you’re there.
I continued exploring Grant Park, and of course I had to get a photo of Cloud Gate (aka the Bean).
Grant Park / Millennium Park / Maggie Daley Park
I stopped at Native Foods Cafe for some vegan food. I wasn’t too hungry so I just got some Thai Chili Brussels Sprouts (sooooo good!). I ended up eating here again a few days later too. They have multiple locations in the city, so add this to your list if you’re vegan/vegetarian.
Address: 218 South Clark Street
I ended the day with some more wandering through the rainy streets, and one last coffee. Then I returned to the hostel for the evening to get some work done.
Address: 12 South Michigan Avenue
Chicago – Day 2
I started day 2 with a latte at Goddess and the Baker. I decided to go here after reading Melina’s post over at Coffee and Fernweh. Check out her Chicago post for more coffee & donut recommendations!
Address: 33 South Wabash Avenue
I never let the rain stop me from going out and enjoying a new place! I spent the morning wandering along Chicago’s Riverwalk with coffee in hand. I ended up walking along the river almost everyday in Chicago simply because it was so pretty. Then I went to the Chicago Architecture Foundation to deep-dive into the city’s architecture. I didn’t end up doing any of the tours, but it’s top of my list for my next visit.
Chicago Architecture Foundation
Address: 111 East Wacker Drive
Admission: $12
I stopped in at Stan’s Donuts on my walk back to the hostel. I had a coffee and decided to try the vegan donut (they have 2 vegan options). The cafe was so cute and it was a nice way to get out of the rain. There are multiple locations throughout Chicago.
Address: 181 Michigan Avenue
I went back to the hostel mid-afternoon so that I could get some work done. HI Chicago has a really great lounge and lots of common areas. It was the perfect place to get some work done! Then at 5:30 they had their free weekly happy hour, so I had some (free) wine and went out for the evening.
Chicago – Day 3
I took things easy on day 3. I went out for another walk around the city, ate at Native Foods Cafe again, and took a break from coffee. I also went to the American Writer’s Museum, which I really enjoyed. If you’re a writer, or just a fan of literature, make sure to add it to your list.
Address: 180 North Michigan Avenue
Admission: $12
Chicago – Day 4
Day 4 was the first sunny day in Chicago. I was originally meant to leave on day 5, but I extended my stay because the sun just had me falling in love with the city!
As usual, I started my day with coffee. First was a latte at Dollop Coffee Co. Then I got breakfast tacos (and another coffee) at a place called Bodega in the River North neighborhood. I would not necessarily recommend the tacos, but the coffee was good. It’s a cute place to get an Instagram photo though (if you’re into that kind of thing), and their desserts look WAY more delicious. I sat on the steps by the river to eat and enjoyed the morning.
Address: 343 South Dearborn Street
Address: 355 North Clark Street
After eating, I walked over to the Museum of Contemporary Art. I ended up joining a free tour through one of the current exhibits (which is something I don’t usually do at museums) and really enjoyed the experience.
Museum of Contemporary Art (MCA)
Address: 220 East Chicago Avenue
Admission: $19
As I continued exploring River North on foot, I decided I might as well head over to the Navy Pier. It was such a beautiful day and the place actually wasn’t all that crowded. The gardens and Ferris wheel were definitely photo-worthy, but overall, the Navy Pier is not a must-visit unless you have kids.
Address: 600 East Grand Avenue
Most of my days in Chicago consisted of wandering around during the day, and then heading back to my hostel in the late afternoon so I could work the rest of the evening. So that’s how I ended Day 4. I hopped out for a quick dinner at Veggie Grill (if you have a Veggie Grill near you, take advantage of it!)
Address: 204 North Wells Street
Chicago – Day 5
I decided to spend day 5 outside of downtown Chicago. I took an uber up to the Lincoln Park neighborhood, and started with breakfast and coffee at Colectivo Coffee. This is a cute neighborhood with some good cafes and things to check out.
Address: 2530 North Clark Street
After coffee, I walked over to Lincoln Park. Here you’ll find the Lincoln Park Zoo, lots of trails and green space. I walked alllll over this park and it was just so nice to have a little bit of serenity within the city. I even walked all the way down to the Chicago History Museum and spent a couple of hours there. I skipped the zoo though; zoos aren’t my thing.
Lincoln Park
Address: 1601 North Clark Street
Admission: $19
Of course my favorite part of Lincoln Park was the conservatory. It’s free to go in, and the displays are so beautiful. I took 500 photos in here and it wasn’t enough!
Lincoln Park Conservatory
I then walked (a really long ways) to the Chicago Diner to eat dinner. It’s an awesome vegan diner in the Boystown neighborhood.
Address: 3411 North Halsted Street
Chicago – Day 6
By Day 6, I became significantly worse at posting stories. I spent the morning walking through the Wasbash Arts Corridor, which starts right across the street from the HI hostel. There are blocks and blocks of artwork to take in, so spend a bit of time with your camera out.
Location: South Wabash Avenue
Later in the day I went to the Chicago Cultural Center. This institution is a multi-floor culture center, with galleries, art studios, and spaces for performances, classes, and more. Entry is free, and you can wander around on your own, or you can join a free guided tour.
Address: 78 East Washington Street
Chicago – Day 7
Admittedly, I was kind of ready to leave Chicago by my last day. There was still a lot I wanted to do, but 7 days of exploring a city gets a bit tiring. I wanted to make the most of my last day though! I went back to Grant Park to get some photos while the sun was out and the Buckingham Fountain was the star of the show. Then I walked westward and did some exploring in the West Loop neighborhood.
Buckingham Fountain
West Loop
My coffee stops for the day were at Intelligentsia and Mojo Coffee. The former is a Chicago coffee MUST; the latter is a New Zealand coffee must…in Chicago.
Address: 200 South Wacker Drive
Address: 53 East Randolph Street
So that rounds up my 1 week in Chicago. I’m sure I forgot a few things here and there, but I wanted to give you guys an overview of how I spent my time there. Like I said, most of my evenings were spent working, so the amount of stuff I did could probably be condensed into a shorter trip. I plan to make an actual Chicago Itinerary and/or a guide soon, so I’ll compile a more organized, succinct list of recommendations then.
I hope you enjoyed this (messy) 1 week in Chicago travel diary! I just wanted to re-share my Chicago stories and try something a little different. Don’t forget to follow me over on Instagram if you want to follow my travels in real time (on stories).
If you want to hear more about the coffee shops I visited, check out my Chicago Coffee Guide! Or check out the 24 Hour Guide to Chicago on a Budget.
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Travel Daze 
This is such a great idea! I loved following your IG stories while you were in Chicago. It’s got me itching to go back!
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Thanks, Melina. Putting this post together made me want to go back too! haha
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Hi Courtney! I loved following your Chicago trip on Insta stories. The city I grew up in is just two hours away in Michigan, but I haven’t spent any time in Chicago for quite a few years. This post definitely inspires me to make a trip to the other side of the lake next time I’m stateside 🙂
Alex | http://backpackingbrunette.com/
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