2 In Like A Local/ North America/ United States of America

Best Of Chicago: Insider Tips From A Local

Last updated on Jun 8, 2018

I’m excited to share this edition of Like a Local because it’s written by my friend Monica, author of the blog From Here To Sunday, who I connected with online over a year ago and met in person for the first time in Bali. We travelled together around Bali and Yogyakarta. Monica will be sharing with us her insider tips and local knowledge on Chicago, read on to find out everything you need to know about visiting Chicago.

View from LondonHouse Chicago, photo by From Here To Sunday

View from LondonHouse Chicago, photo by From Here To Sunday

Hi Monica, tell us a bit about yourself! What city do you feel like a local in?

While I wasn’t raised in Chicago, I lived there for two summers and feel like I’ve gotten to know it pretty well from visiting my sister over the years.

What are your favourite places to eat?

Chicago is KNOWN for its food so you really can’t go wrong answering this question in my opinion. If you do Chicago right, then you’ll find yourself eating at some of the famous deep dish pizza restaurants and burger joints. My favorite deep dish is at Lou Malnati’s and I frequent the one in the Gold Coast the most and my favorite burger is at Au Cheval in the West Loop (where you will undoubtedly wait in a very long line and it will be well worth it).

Monica and the Chicago skyline, photo by From Here To Sunday

Monica and the Chicago skyline, photo by From Here To Sunday

Do you have a favourite place to study or work?

I work from coffee shops nearly everyday and there are just too many to choose from! Just to name a few, my favorites are: Freehand ChicagoWormholeTwo Hearted QueenNew Wave Coffee, and Sip Coffee House. These are scattered all around Chicago as I like to switch up the neighborhood I work in so I have varying lunch and happy hour options 🙂

What about when you want to relax? Do you have a favourite relaxing spot?

Chicago has so many parks and beaches along Lake Michigan and since I enjoy spending my time outdoors, I can easily relax in any one of them (Lincoln Park, Montrose Beach, Grant Park, etc.). I also enjoy rooftop bars and lounges such as the 3 Arts Club Cafe in the Gold Coast. One of my favorite spots to go with my sister is this tiny triangular park off of the Clark/Division stop called Mariano Park, it can be found on Rush and State street. There’s a cute gelato shop and in the summer everyone hangs out here and people and puppy watch.

Sunset views over Chicago, photo by From Here To Sunday

Sunset views over Chicago, photo by From Here To Sunday

Is there a typical activity locals do in their free time?

I find the people in Chicago to be pretty active, I see a lot of bicyclists, joggers, and activities on the water like kayaking, boating and canoeing. Since winter takes over most of the year, there are also tons of indoor activities as well. Given the majority of locals are die-hard sports fans, there are a ton of sports bars and restaurants to spend time in.

What is your favourite activity or thing to do in Chicago?

My favorite thing to do is spend time at the beaches and parks!

Street art in Chicago, photo by From Here To Sunday

Street art in Chicago, photo by From Here To Sunday

Do you have a favourite photo spot?

I think the area in Grant Park around the bean is a popular area. There are also countless rooftop bars to go to which offer epic views of the skyline, including LondonHouseCindy’s Rooftop Bar, and Hotel Lincoln, to name a few.

When is the best time to visit Chicago?

Summer for sure, a lot of people can’t handle Chicago winters (myself included)!

What’s one “touristy” thing in Chicago everyone should actually do?

Hands down the architecture river cruise, informative, interesting, and fun! I’ve always gone with Wendella Boats, they’re the most known.

Chicago travel guides worth checking out:

Lonely Planet Chicago (Travel Guide)
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Enjoying the rooftop bars of Chicago, photo by From Here To Sunday

Enjoying the rooftop bars of Chicago, photo by From Here To Sunday

What’s one “off the beaten track” place people don’t normally know about but should visit?

I love visiting the Montrose Point Bird Sanctuary north of the city, it’s beautiful in the summer time with views of the skyline downtown, flowers everywhere, and Lake Michigan. I don’t often see tourists here so definitely “off the beaten path”, it’s free and beautiful!

Any tips or tricks on how to navigate Chicago?

Fly into O’Hare International Airport and you can get on the subway (the Blue Line) straight into the city. The “L” (elevated train) gets you most places but I also take the city buses. Uber and Lyft are also easy options available everywhere.

Chicago beach and city skyline, photo by From Here To Sunday

Chicago beach and city skyline, photo by From Here To Sunday

Any tips on how to visit Chicago like a local so that travellers reading this can blend in?

When you go to restaurants, cafes, shops, any establishment really – BE FRIENDLY and say hello! Chicago is a super friendly place so the best way to blend in is honestly just to be nice!

What do you love most about Chicago?

The energy in summer time. Chicago experiences pretty rough winters, so when summer time comes around everyone is really happy and you can feel the vibes as soon as the sun comes out.

Museum of Contemporary Art Chicago, photo by From Here To Sunday

Museum of Contemporary Art Chicago, photo by From Here To Sunday

Anything else you want to share about Chicago?

My biggest recommendation is to make sure you spend time in the variety of neighborhoods that exist, as they all offer something different and unique. Obviously spend some time downtown and in the touristy areas (they’re touristy for a reason right), but also go to Wicker Park, Lincoln Park, Gold Coast, West Loop, Logan Square, Old Town, Lake View and Avondale. Or at least as much as you can fit in your schedule 🙂

What is the best area in Chicago to stay in? Any specific hotels you can recommend?

If you stay in River North you will be pretty central to just about everything. Here’s a few hotel recommendations:



Booking.com

Have you been to Chicago before? How did you find it? Let us know in the comments below!

Enjoyed reading these Chicago insider tips? Pin it!

I asked a Chicago based travel blogger to share all her insider tips on Chicago. Find out everything you need to know about Chicago with this local's guide. #chicago #insidertips #localtravelguide #usa #unitedstatesofamerica #travellikealocal

I asked a Chicago based travel blogger to share all her insider tips on Chicago. Find out everything you need to know about Chicago with this local's guide. #chicago #insidertips #localtravelguide #usa #unitedstatesofamerica #travellikealocal

I asked a Chicago based travel blogger to share all her insider tips on Chicago. Find out everything you need to know about Chicago with this local's guide. #chicago #insidertips #localtravelguide #usa #unitedstatesofamerica #travellikealocal

About the author

Monica is a digital nomad that who has worked, lived, volunteered and travelled to over 45+ countries. Her blog From Here To Sunday is dedicated to the idea that you should never stop exploring, and it aims to inspire people to step out of their comfort zone and travel somewhere new.

Website | Instagram | Twitter | Facebook | Pinterest

Street art in Chicago, foto by From Here To Sunday

Monica author of From Here To Sunday

* This post contains affiliate links. Greta’s Travels is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to Amazon.com.  As an Amazon Associate, I earn from qualifying purchases. Greta’s Travels is also a participant with the Booking.com Affiliate Program. All purchases or bookings you make through Greta’s Travels come at no extra cost to you. *

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2 Comments

  • Reply
    Monica Houghton
    June 8, 2018 at 6:26 pm

    Thanks for sharing all of these tips with your readers, Greta! I hope they are helpful 🙂

    • Reply
      Greta
      June 8, 2018 at 7:12 pm

      Thank you for taking the time to write them! 🙂

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