Guide to Chicago

It’s crazy that this was my first trip to Chicago! (I don’t count the trip I did at 9 years old with my aunt and uncle) It was my first time exploring as an adult and with the intent to write about it! I stayed in Chicago for almost a week! For the first 3 days I  was the ultimate tourist and for the second 3 days I was the ultimate Bachelorette party attendee.  I think it’s safe to say thought that from the two different angles I have a pretty good handle on Chicago! I went to most of the major areas, sights as well as well as many of the trendy places to eat and drink and out it all into this Guide to Chicago!

Getting There

It would be about a 13 hour drive from NYC to Chicago so like most people would,  I opted to fly!  I flew into O’hare International, but there is also Midway Airport nearby. From O’hare Airport you can take the blue line “L” train for about a 45 minute journey into the city. One way cost is $2.50.

If you’re staying in a hotel, always check to see whether or not they provide an airport shuttle and whether it’s complimentary.

Getting Around

I ended up purchasing a 3 day unlimited Ventra card. The cost of a 3 day unlimited card is $20 and works on both the bus and train. Chicago is definitely not a city where a car would be necessary. Walking and public transit worked out just fine for me with the occasional uber ride.


Where to Stay

Thompson Hotel– located in the downtown Gold Coast area, The Thomspon Chicago is a trendy and modern hotel with plenty of comfort. Nico Osteria is an Italian restaurant located at the hotel and the food and service was delicious!

double beds in hotel room


Fairmont Chicago–  is overlooking Millennium Park and has an incredible view of Lake Michigan. This Hotel is fully equipped with a fitness studio, Spa and tap room.


breakfast on Hotel bed

What to Do

Check out the Park – Millenium Park

If you didn’t go to see Cloudgate aka The Bean while you’re in Chicago, were you even there? There is plenty to do at the park but the Bean has definitely become one of the top attractions.

See a Show at Chicago Theatre 

A variety of music and performances and sporting events are held here so make sure you check the schedule!

girl standing outside Chicago theatre

Chicago theatre

Cruise the river  with First Lady Boat Cruise

This was one of my favourite activities in Chicago! It was a perfect start to the trip and such a great way to gain perspective and insight into the city, especially if you’ve never been before.

Have a Spa day at Aire Ancient Baths 

Aire Ancient Baths experience in Chicago is unique anything else. You literally feel like you’ve stepped into another world! With no sign of the city at this discreet location you can fully relax. They even have a salt pool (flotarium) with music under the water!



Take in City Views at Sky Deck

The Sky Deck is located in the Willis Tower and features unparraelled views of Chicago. Go out on the ledge for the best shots! Be warned that you do have to queue up and they time you to take pictures but you can go back around if you want more time. I definitely suggest trying to be the first one in to decrease wait time.

Escape the city at Griffith Conservatory

FREE to enter (donations encouraged) conservatory with an “L” stop just yards away. Home to all sorts of plants and they even had baby goats when I was there!


Where to Eat and Drink


This globally inspired restaurant had me in my happy place! The lush decor, curated cocktails and inventive food make it a must while in Chicago!


A spy themed interactive restaurant. Fun for the entire family. This will definitely bring out the kid in you!  I was very impressed with some of the lengths they went to for the theme!


I hope you enjoyed my Guide to Chicago…Food & Drink Guide coming soon!


Check out my Guide to Chicago’s Best Instagram Spots here

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