Monday, March 7, 2016

City Guide: Chicago, IL

In the beginning of October, I flew out to Chicago for a quick weekend trip. Honestly, I love the short, two day trips more than spending an entire week exploring a new city. This forces me get the day started early, plan out my itinerary, and be as strategic as possible. Below are some of the best places I found while I was exploring Chicago. I still can't believe how much I was able to explore in such a short window of time!


My first AirBnB experience was when I went out to Chicago. It was a bit of a last minute trip so hotels were a little pricey and I wanted a more authentic experience; I really wanted to feel as if I was living in the city for the weekend. I really believe the best way to see any city is through the eyes of a local and my host provided excellent recommendations which really made my trip special.

I stayed in the Lakeview section of the city which reminded me a lot of Fairmount in Philadelphia, PA {where I currently reside}. You were able to walk around to many different restaurants,bars, shops and the location was pretty close to Lake Michigan as well. It was because of this trip that I decided to use AirBnB when I went to Miami in February.


Pequod's Pizza
Prior to this trip, I had never had deep dish pizza. I had done a lot of research and narrowed it down to two places. How did I decided on Peqod's? Well I asked my waitress at lunch earlier that day for a recommendation and she raved about this place. The place was pretty crowded and they do not take reservations but I was able to grab at drink at The Drinkingbird {located next door} while I waited. When it came time for pizza, I was starving and couldn't wait to give it a try. It was good, but extremely filling. I could barely eat two slices! It was worth the experience, but I still prefer my New York style pizza.

Heritage Bicycles
I stumbled across this coffee/bike shop when looking for an afternoon pick me up. It is such a unique concept; the store sells and repairs bicycles but also has the most adorable coffee shop I have ever seen. I had a cup of their pour over and brought my coffee {and pastry} outside to a bonfire they had set up adjacent to the store. It was such a great experience and I was so happy to find this hidden treasure.

S&G Restaurant
If you are a fan of diners, endless coffee and a big breakfast then I recommend you make your way here if you are ever in Chicago. I had breakfast here both days of my trip. The staff was extremely nice and you could tell there were a lot of regulars coming in for breakfast, which is always a good sign of a great restaurant.

Local Root
I stumbled across this place accidentally when I ended up getting lost on a walk, but after reading the menu I decided to stop in for lunch. Everything at Local Root is sourced locally and they are a no-waste restaurant. I was having such a great time talking to the staff that I decided to stay after lunch for a few beers. Everyone was so friendly and the food was extremely fresh and delicious.


Architectural Boat Tour
If there is one thing that you have to do while visiting Chicago, it is this boat tour. The city looks absolutely spectacular from the river and the tour guide I had was wonderful and funny. It was not only fun, but educational and informative as well. I left having a greater appreciation for architecture and a better understanding as to why some buildings look a certain way.

Lake Michigan
As a first time visitor to the Midwest, I was pretty excited to get to see one of the Great Lakes. Chicago sits right along Lake Michigan and it is quite the sight. The weather was pretty warm the weekend I was there so the river path was filled with runners, walkers and bikers. I was glad to experience the beautiful scenery and enjoy a long walk prior to leaving for the airport.

Lincoln Park Conservatory
I accidentally stumbled across this place after checking out The Lincoln Park Zoo {which is free if you are interested in exploring the Zoo}. The Conservatory was stunning with different rooms filled with ferns, flowers and palm trees. There is also a large lawn right outside of the entrance where many people were reading and playing board games with friends that day.

Other Notables: The Bean, The John Hancock Building, The Magnificent Mile - Michigan Avenue, Navy Pier, Wrigley Field

Interested in more City Guides - Check out my Miami Beach Guide, Philadelphia Food Guide and Hoboken Food Guide


  1. We are just 2 hours from Chicago and go all the time! So fun and so much to do!! The boat tour is amazing! So glad you got to spend time in the Windy City!!! ;-) Happy Monday!!

  2. I haven't been to Chicago in a few years and it's definitely a favorite city of mine!! I want to head there in the summer when it's warm haha! xo, Biana -BlovedBoston

  3. Chicago is my favorite city - just love it there!

  4. Chicago is such a great place to visit, there's just so much to do! I love that you stayed at a b&b!


    Whitney & Blaire

    Peaches In A Pod

  5. This post is great! We are hopefully planning a trip to chicagoninnthe next few years so I'm definitely pinning this!!

  6. I've never been to Chicago but I REALLY want to make a trip up there soon! That boat tour sounds amazing! <3, Pamela Sequins & Sea Breezes

  7. yes to all of these! that's rad you did an airbnb for your stay i still haven't tried it. i love visiting all the sights there and october seems like a good month! i went in the spring which is also fun :) good rec's!

    xoxo cheshire kat

  8. I love taking short trips, too, and Chicago is one of my favorite places to visit! You can't beat the shopping on The Magnificent Mile.

  9. All of your pictures are so pretty! I've visited Chicago a few times and I love exploring the city!

  10. What a fun trip. Chicago is on my places to visit! So many great things to do and see!

  11. Amazing pictures, great post as well, thank you for sharing!!!


  12. Oh how I love Chicago! It nudged out NYC as my favorite US city! The architectural river tour is definitely a must-do, and the food - oh the food! Such an amazing city <3
    Green Fashionista

  13. Great guide! I LOVE Chicago!!

  14. Seriously what a great city guide!!! I love love love this! happy Monday!

  15. This is such a great guide! I love short weekend trips, too. I was just in Chicago in August, but I was there for a conference so I didn't get to do much sightseeing. Such a fun city!

    xo, Rachel
    A Blonde's Moment

  16. I would LOVE to visit Chicago some day! Such a great guide, thanks for sharing!
    xo, Lily
    Beauty With Lily

  17. sweet!! I've always wanted to visit Chicago! One day, definitely bookmarking this post!

  18. I still haven't been to Chicago and I'm dying to go, great city guide! How did you love Air BnB? That's something else I haven't tried yet but I've only heard great things!

    xx Jesica

  19. Weekend trips definitely require you to be a lot more strategic about where you want to go and what you want to see when you're traveling. The Architecture Tour was probably my favorite thing that we did when we visited Chicago last year! All of the buildings are just so pretty!

  20. I would love to visit Chicago one day! I have never been but it is on my bucket list. I am actually working on a portfolio in Cook county for work, but all my work is remote.

  21. I'm from Chicago (living in Minneapolis for many many years now though) and I love this list! Pequod's pizza is SO GOOD! I love that you included it on this list! And that boat tour is so great on a nice summer day!


  22. I would love to visit Chicago soon! Love your photos! =)

    - Cielo
    Mermaid in Heels

  23. Chicago seems like such a nice city! Great photos!


  24. I absolutely love Chicago! Such a fun city and a great place to use Air B & B!

  25. Great guide! I really want to visit Chicago!

    Amy Ann
    Straight A Style

  26. I have yet to go to Chicago but I hope to make it soon. Love this short trip.

    XO Chelsea

  27. I love visiting Chicago! It's such a great big city and the people are usually very friendly in the Midwest. I've never heard of Local Root but I love the concept. And I think staying at an AirBnB is a great way to save $$$ and get a cool experience.

    xx Yasmin

  28. Omg, I want to visit Chicago so badly! I always wanted but after your post dear I want to visit even more!!! <3

  29. Great review! Nice pictures!

  30. I went to Chicago once and really enjoyed it...need to go back!

  31. I love Chicago but have only gone there for work!!! I've been able to sneak in a few touristy things, but I would love to do the architectural boat tour you mention! Love the idea of staying at an AirBnB too!

  32. I adore this city. We also went for a weekend trip a couple years ago and fit in most of your site-seeing recommendations although I didn't eat (or see) any of those restaurants. The restaurants we did eat at were amazing though so no regrets. AirBnB is a great idea!

  33. We are currently living in Chicago for a year, and it's such an amazing city! This is a great list! Architecture boat tours are my favorite. We have done four with various visitors so far this year! Haha. Next time you come to Chi, try Lou Malnati's-their butter crust deep dish is amazing, and the tiramisu is the best I've ever had! ;)

  34. This is a fabulous guide, I've never been to Chicago but it's on my list. Thanks so much for sharing. Love, Kirsten

  35. Hi there! I could have sworn I've been to this website before but after looking at some of the articles I realized it's new to me. Anyhow, I'm certainly pleased I discovered it and I'll be bookmarking it and checking back often! facebook sign in