In Planning, Trips & Tips on
September 7, 2016

Simple City Guide to Chicago: The Windy City Edition

city guide to chicago

Chicago is hands down one of my favorite cities on Earth. It has delicious food, towering skyscrapers (I mean, that skyline!), world class museums and a bustling nightlife. All of which make the Windy City a top holiday destination. It’s a fabulous destination for families, both foreign and domestic alike, due to the amazing Lincoln Park Zoo and Shedd Aquarium. If you’re young and looking for a fun weekend warrior trip, hit a Cubs game and bar hop around Wrigleyville. Whatever you fancy, there is something in Chicago for every traveler.

Simple City Guide to Chicago: The Windy City Edition

city guide to chicago

What Chicago airport should I choose?

Fly into Chicago Midway and avoid O’Hare International if possible. I mean, have you seen Home Alone? O’Hare is a huge airport, further away from the city and has a history of delayed flights. Midway on the other hand, is smaller, closer to the city and has notoriously shorter security lines. The only caveat to Chicago Midway is that not as many airlines fly into there, so be sure to choose airlines such as Southwest .

Where should I stay in Chicago?

A hotel along Magnificent Mile or The Loop makes for a great home base while in Chicago. Being along Mag Mile will offer a close proximity to great shopping, restaurants, Millennium Park, Lake Michigan and Navy Pier. Great options along Mag Mile are: Chicago Marriott Magnificent Mile and Double Tree MagMileThe Loop makes for a great option if you want to explore the city by train while still staying in close proximity to all the highlights. Great hotel options within the Loop are Hilton Palmer House and The Waldorf Astoria.

palmer house chicago

Free things to do in Chicago…

One of the things that I love most about Chicago is the abundance of fun and free things to do. Below is my list of amazing free things to do in the Windy City.

  • Lincoln Park Zoo
  • Millenium Park
  • Magnificent Mile
  • Checking out Chicago River Walk
  • Navy Pier
  • Beach Day at Lake Michigan
  • Lakefront Trail
  • Chicago Cultural Center
  • Lincoln Park Conservatory

lakeshore bike path chicago

navy pier

millenium park chicago

Where to party in Chicago?

Bar hop in Wrigleyville. Enjoy a cocktail from a Chicago rooftop bar. Or get secretive and go to a speakeasy for fun libations.

What else should I do in Chicago?

There is so much to do in Chicago. If you’re a sports buff, check out a Cub’s game at the historic Wrigley Field. If you want to be like Ferris Bueller, grab your friends or a loved one and check out the sites from Willis (formerly Sears) Tower. Below are additional ideas of fun things to add to your city guide to Chicago.

city guide to chicago

chicago theatre

What should I eat while in Chicago? 

I know what I am about to put is going to be found in any city guide to Chicago, but there is a reason for it.  These foods are damn good. Here are my top (and very touristy) choices for what to eat in Chicago.

  • Chicago-style Hot Dogs: Beef frank in poppyseed bun with all the fixings. DO NOT GET KETCUP. It’s insulting. Try Jim’s Original
  • Chicago-style Deep Dish pizza. Oh Lord. We ate at various establishments and honestly cannot get enough. Go ahead and get down with your bad self with the meat lover. Locals and travelers all have their personal favorites, from Lou Malnatis to Pequod’s Pizza
  • Eat at a fancy steakhouse. There is something about a classy sub-basement steakhouse that makes me feel like I could be in a scene from Boardwalk Empire. Try Bavette’s Bar and Boeuf.
  • Get popcorn. Sounds random, but Chicago is famous for their popcorn. Grab some from a Garrett Popcorn Shop.

chicago style deep dish pizza

chicago style hot dog


I hope you liked my quick and simple city guide to Chicago, the Windy City edition. If you have any other additional questions about what to do, when to go, or even what to wear, feel free to reach out to me: chloe (at) I hope you have a fabulous day and thank you again for stopping by!



the bean chicago

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  • Anna At Lifestyle Crossroads

    Great post full of useful tips and ideas! This food section got me hungry though…lol! Chicago views are breathtaking!

    • Haha!! I know! The food is to die for. I just got hungry again just looking through it haha!!

  • I avoid O’Hare like the plague. We’ve lived here for five years now and if we can help it, we don’t fly out of O’Hare. I’m usually not a deep dish fan but Giordano’s is awesome.

    • Haha!! O’Hare is the devil of all airports, I swear!! I’ve heard that too about Giordano’s, we’ll have to try that next time 🙂

  • TravelBlond

    I’m happy I came cross this article because I am planning mt trip to Windy City! While staying option is already included (friends), the airport choosing was an eye opener for me. I like how simple you wrote the Chicago Guide. Super helpful !

    • Thank you, lady!! I hope that this helped you plan your trip to Chicago! It’s so much fun and I’m so excited for you to visit!

  • I only visited Chicago briefly, so I didn’t get to do a lot of this stuff. I did do some shopping on Magnificent Mile and make a quick trip to the Navy Pier. I hope to visit again soon.

    • Oh ya, Chicago is def worth a weekend trip. Luckily a lot can be covered in a short time but def go back! It’s so worth it!

  • I need this hot-dog in my life!! It looks so yummy! All the photos look great actually, loving the skylines! And who doesn’t love to know all the free stuff to do! This is always the first stuff I look up about a place ha! And loving the fact you mentioned O’Hare airport as the Home Alone airport haha! Puts things in perspective to those who are not from the US. It’s like the most known series of movies in Estonia. E v e r y s i n g l e xmas it’s on TV and e v e r y s i n g l e person watches it every year. Most have seen them for fifty times and still keep it on when it comes from the TV. Haha! Thanks for sharing this! I’ll pin it for later 😉

    • That hot dog can change lives with how good it was. And I love hot dogs… haha!! And I loved that you knew with Home Alone!!! It’s one of my favorite movies too and whenever I go to Chicago O’Hare I always think of Kevin McAlister hahaha!

  • I absolutely loved Chicago when we visited! It’s so beautiful in the summer and I would absolutely love to go back one day. Such a great guide – it’s fabulous that there’s so many free things to do in Chicago. Thanks for sharing Chloe! #FlyAwayFriday

    • Isn’t it gorgeous in the summer?? So much to do and everyones out and about. I love it!! So much fun!

  • Mimi Rose

    I love this post! I just went to Chicago for the first time for my birthday in May and I thought it was a great city. The deep-dish pizza is ridiculously good and one of my best friends is moving there next month, so I’ll definitely have plenty of reasons to visit. 🙂

    • OMG how good is the deep dish pizza?? We had it THREE times when we were there hahaha #noshame!!!!

  • Kim

    Thanks Chloe! I love Chicago…was actually meant to move there years ago for a new job, but moved to Australia instead #Lifechanging

    • OMG! How cool! You never know, you may find yourself in Chicago at some time or another 🙂

  • Richard

    Thanks Chloe – I really like the “simple city guide” format. We got married in February — not necessarily the ideal month for going to Chicago — and had a memorable anniversary staying at the Palmer House, trudging to the blues clubs in the snow, and having pizza at Gino’s. Thanks for the reminder!

    • Thank you Richard!! I really appreciate that! I bet you had a beautiful wedding in Chicago!! It’s hard to go wrong there, no matter what month!!

  • Love C and D

    Great post and thanks for sharing. As Richard says, this “simple city guide” format is awesome, providing lots of information in a easily readable format without information overload. The food sounds and looks absolutely delicious too! We have never been to Chicago and until I had read this i can’t say i ever planned to but now…Chicago here we come (one day)!

    • Hey! Thanks guys, I found it to be easier too. My attention gets lost when I read really long travel guides, so much easier to just bullet point the good stuff! The food is amazing, I hope you guys find yourselves in Chicago sometime in the near future, it really is such a fun place!

  • I’ve not been to Chicago but there is one main reason I would love to go – the jazz!! So much jazz history in Chicago it would just be incredible to be there just to listen to such an iconic music genre. Plus I’d love to bike along the waterfront too. Great post!

    • OMG there is so much jazz history there. I hope you guys go to check it out some live jazz and their blues are famous too. And can’t skip a speakeasy!!!

  • Ironically I shared a post about Chicago for #FlyAwayFriday too! I loved the city, it had such great energy to it and had so much to offer. I found there was plenty of exploring and things to see everyday. Your post made me miss the city’s energy and life!

    • Right?? You’re absoltuely right. There is a great energy about it and I love that the people of Chicago love their city, it’s very contagious 🙂

  • nattiekaf

    I really like the simple guide to a city, gives you the gist with out getting too info intense! Chicago seems awesome, I haven’t had the chance to check it out yet, except for spending 7 hours in O’Hare a few years ago on a delayed layover(man that airport felt like a huge confusing mess). And as always awesome pictures!

    • Hey! Thank you, I do too. I started writing a longer, city/travel guide and found it’s easier to bullet point it. Think it gets the point across easier and holds the attention of the reader for longer. OMG!! I am so sorry you were delayed there for that long, I’ve been delayed there too many times myself!! Hope you find your way to Chicago sometime soon! xo

  • claudi

    I’ve heard so much about Chicago and your post makes me even more want to go there!! <3

    • Omg Claudi you need to go!! You will love it! So much to do and amazing food!!

  • LOVE Chicago. Went back in February and I didn’t even care it was freezing my fingers off, I just love that city. It’s so smart you wrote about which airport to fly in and out of since that’s something people ask me all the time! #FlyAwayFriday

    • I love that city too!! It’s amazing and so much to do!! And oh ya, O’Hare is the devil!

  • Very useful tips and detailed information about Chicago. I wish to go there one day, it seams amazing!

  • Thank you for this comprehensive guide of the Windy City. It is definitely high up on my bucket list, so will definitely save these tips and places for later!

  • Vishal

    I agree with you to avoid O’hare. That airport in my opinion is punishment. Not a lot of people like travelling there.

  • You definitely conquered me with that Chicago deep dish pizza. I would visit Chicago for it only. Also, I would love to take part in a jazz gig in an underground bar, imagining I’m back in the times where Chicago was rules by gangsters 🙂

  • Editor-in-Style Good

    My cousins live in Chicago and I am due for a visit! I cannot blame you for avoiding O’Hare airport! It is crazy at every time of year! The Lincoln Park Zoo appeals to me.

  • Arnav Mathur

    This is one hell of an informative post about Chicago.I personally would love to go on a river cruise post sunset and go on a food trail.The pictures of the various dishes look so yumm.

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