Visiting Chicago with Porter Airlines


Porter Airline trip Photos: Monique Simone Photography & my own travel shots!

On June 23rd I took off with Porter Airlines to visit Chicago, Illinois. If you did not already have the chance to see, you can check out my earlier post where I discussed what travel influencers really have become. We are helping you shape your destinations, discoveries and adventures and asked all of you to help curate my trip to Chicago. I shared a few questions and received tons of responses on social media (thank you!).  Porter and I asked our followers on Facebook, Instagram and the blog to help create a trip that would really showcase what YOU wanted to see. From this, I created the perfect itinerary for my 3 days in Chicago. Brace yourself, it was action packed!

As you scroll through this blog post you will see plenty of amazing things I did during my time in Chicago. Some photos, some comments and great eats! I will share with you all a photo diary later of all the awesome spots in more detail during my stay.

The end goal has been to really share how INCREDIBLE Chicago is as a city. I also want to share how easy it is to get there via Porter from Montreal or Toronto. I’ve visited in the past, sharing this incredible city with you all, full of life, art, business, culture, food and FUN.

People are always asking me why I fell so in love with this city and continue to go back time and time again. From the food and cocktail wizardry of chefs like Grant Achatz, to art and design like the famous BEAN by Anish Kapoor in Millennium Park, the city is full of culture and stories and really really nice people. I emphasize the nice people because over my time in Chicago I have met some amazing humans. They have helped me make great connections and have wonderful experiences. I stay in contact with them on a regular basis and am so thankful!

This time, Porter Airlines gave me the opportunity to return and experience it like never before. Porter stole my heart some time ago and continues to do so over and over again (which is why I love to work with them!!). The staff is incredible, the service is great, the lounge and planes are beyond accommodating. Of course the added bonuses like coffee and snacks are just the icing on it all. I am so fortunate to work with this airline.

In three days I really covered as much as I could for all of you to see, hear, watch, read about. I have so many more stories and suggestions that I can’t possibly all share here. Please do not hesitate to reach out with more questions. I would be so happy to answer anything about this incredible city for those who would like more detail.

Before I share it below, keep in mind I was trying to cover as much as possible for all of you to see. Tackling everything in one trip may not be possible for everything. But that’s why okay, since Porter flies from Billy Bishop Toronto City Airport to Midway International Airport multiple times a day! Take this itinerary with you when you fly Porter to Chicago on your next long weekend getaway and I hope I helped you discover something that makes you smile 🙂 Enjoy!

June 23rd:

Flight from Toronto the Chicago




Hung out in the Porter lounge and checked out the cockpit of our plane!



Checked into Fairmont Chicago Millennium Park


Had Lunch at Cindy’s Rooftop


Walked  Millennium Park exploring The Bean, the new outdoor concert venue and Crown fountain!



Sipped a coffee at Intelligentsia


Headed to the Riverwalk, heard live music and sipped wine at Bridgehouse!

Had dinner at Imperial Lamian followed by drinks at the Aviary (one of the most incredible mixology experiences I have ever encountered by Grant Achatz!!)


June 24th

Started my morning with a run at Navy Pier


Experienced a Fairmont Hotel Tour & Beer Tasting at Columbus Tap


Walked Michigan Avenue, munched on donuts from Glazed and Infused.

Ate Lunch at Federales


Explored West Loop spots like Green Street Smoked Meats, Expat, RM Champagne, Soho House and Bombobar!






Drinks at London House Chicago Rooftop



Dinner at RPM Italian followed by dancing at Celeste


June 25th

Spa visit at Fairmont Chicago’s incredible Spa!


Coffee at 3 Arts Club Cafe and Explored Restoration Hardware



Explored North Loop and the golden square mile, visiting Suit Supply Chicago Rooftop and having lunch at Maple and Ash


Snack at Dough Bros


Afternoon at the Oak Street Beach


Headed up to Lincoln Park for Dinner at Summer House Santa Monica, Kareoke and late night snack at Taco Join!


June 26th

Brunch at the Fairmont Gold lounge before my flight back to Toronto from Chicago!



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    • Jon! Had mostly video links from there. I will be posting a photo diary up soon with more images.

      Thanks for following along.

  • Thank you so much for sharing this! I will definitely be following your intinerary in my upcoming trip (next month, can’t wait!). I was wondering if you recommend making reservations for the Aviary? We are making reservations for the restaurants (dinners), but I wasn’t sure if it is necessary for drinks. Thanks again for this fabulous post!

    • Hey Silvana!

      Thanks so much for following along. Glad my itinerary could help you out on your next trip to Chicago. I would absolutely call and make a reservation. We managed to get a seat without one but we were lucky and visited pretty late. It is in west loop near plenty of restaurants you could check out before hand as well.

      You will love it! What an amazing experience.