My Guide To Chicago Pt. 1 (Day 1-3)

As most of you know, I’m just back from a trip to the ‘Windy City’ aka Chicago, Illinois after spending 6 magnificent days there from Thursday 27th October – Tuesday 1st November. Despite being a regular visitor to the US, it was my first (definitely not my last) time visiting Chicago.


I booked my flights with Aer Lingus and flew direct to O’Hare International Airport from Dublin. At the moment the Aer Lingus flights are for nothing, you can fly direct to Chicago for as little as €219*.  (*offer valid until the 14th of November 2016 on

Fares include a 23kg baggage allowance, complimentary meals and drinks on board plus complimentary access to an in-flight entertainment system that is second to none. (Trust me, I’ve travelled on many other airlines and Aer Lingus is the only one that offer business class service at economy level! Other airlines wouldn’t so much as give you a cup of tea plus they make you pay for access to movies!)

By the way, I should also note especially for those of you who haven’t travelled to the US in a couple of years, you must now apply for your ‘travel permit’ or ESTA online prior to departure here: and you must do so AT LEAST 72 hours prior to travelling. Once your ESTA has been approved, your authorisation is generally valid for multiple trips to the US over a period of 2 years.

For added convenience US pre-clearance is now available in Dublin Airport meaning you clear US Customs & Immigration before you even board your flight! This means that when you land, you simply have to collect your suitcase and walk out the door!

My mom and aunty travelled with me, albeit on a different airline and they didn’t have as cushy an experience as me to say the least. First of all we left Dublin at the same time yet because they flew indirect via Newark, they arrived into O’Hare a good 3/4 hours after me! Because the turnaround was so tight when they disembarked in Newark, their luggage didn’t make it to Chicago either! (It was such an ordeal, you can watch the drama unfold in the video below!)

On the Aer Lingus flight I was served a snack (pretzels & a soft drink), a meal (Irish beef, vegetables & potatoes, bread roll & butter, side salad & chocolate mousse followed by tea/coffee ) and a chicken salad sandwich. My mom and aunty both got fed just one meal between two flights (as they don’t serve food on domestic flights in the US) and were famished again they arrived in Chicago.

Given how cheap the Aer Lingus flights are at the moment it’s safe to say it won’t be for financial reasons you’ll have to fly indirect to Chicago, but just bear all of the above in mind if you are ever faced with the predicament of choosing direct or indirect flights! If it was a case that the direct option was a little more expensive, it’s worth paying a little extra to arrive there earlier WITH your luggage! Not to mention the complimentary five star cuisine and unlimited access to box office movies during the flight!

Finally the three of us were on our way to our hotel, The Raffaello Hotel. I’ll take you on a quick tour around my Deluxe Suite the night we arrived in the video below! Because my mom and aunty had no luggage, we decided to take it handy and have a tipple in the hotel. On the 18th floor of the hotel lies a roof top bar serving spectacular views of the city called Drumbar, voted one of the Top Ten bars in Chicago.

The next morning we woke up really early as Chicago was 6 hours behind at the time (now 5 hours as our clocks went back) so 8am in Chicago was 2pm in Ireland! We went straight to Water Tower Place (an 8 level shopping atrium on Michigan Ave) for some brekkie and browsing. I read about Water Tower Place on the Aer Lingus website because not only can you book flights on the website, you’ll also find really good recommendations for things to do and see, restaurants, bars & nightlife, cafes etc depending on what city you’re going to!


After we did a spot of shopping we went on an Architectural River Cruise down the Chicago River which also came recommended on the Aer Lingus website! I have a massive interest in architecture naturally as I studied History of Art in college but even for those of you who wouldn’t classify yourselves as massive architectural fans, you’ll get to witness the most amazing, unobstructed views of the city that you wouldn’t get to see otherwise and I would highly recommend it for that reason!



The tour is about 75 minutes in duration but there’s a bar downstairs that serves Baileys hot chocolate and margaritas, what more could you want?!


We chose Shoreline Sightseeing as our tour operator for the River Cruise. The price of an adult ticket for the Architectural River Cruise is $39 however, when we bought our tickets we decided to go for a bundle package meaning we got the ticket for our River Cruise and a Big Loop 2 Day ticket for the Chicago Big Bus Tour for just $50! The Big Loop 2 Day ticket is $50 alone so we basically got the River Cruise for free!

We didn’t buy our tickets online prior to travelling either, we bought them at a little kiosk situated on Michigan Ave which is featured in my video below should you need a reference. It’s very easy to find, located at the top of Michigan Ave right at the tip of the ‘Big Loop’. It’s also very close to the location where you embark on the boat tour.

That evening we ate at a restaurant across the road from our hotel called Bar Toma,  the pizza there is divine! It was a quick in and out job because we were wrecked! 8pm there was 2am at home remember!


On Saturday morning we enjoyed a mouth watering breakfast at the Grand Lux Cafe on Michigan Ave which again came recommended on the Aer Lingus website. (We got so many great recommendations on there, you should really utilise their website more when planning trips!)


I’d highly recommend a trip to the Grand Lux Cafe if, like me, you’re a HUGE fan of Eggs Benedict!


We then embarked on the Big Bus Tour around Chicago! There are so many Bus Tour Operators located around the city but went with Big Bus Chicago as mentioned above because it came as part of a bundle package alongside our Architectural River Cruise with Shoreline Sightseeing.


There are 14 stops in total on the Big Bus Tour covering some of the top tourist attractions in Chicago and you have the option to get off at every one if you wish or none, it’s totally up to you!


(You might recognise the above street, it’s featured in The Dark Knight!)


(Popcorn is a BIG deal in Chicago and Garrett is the place to go for it!)

 The Chicago Big Bus Tour also brings you to the best spot in the city for uninterrupted views of the Chicago Skyline!


Buses come by every twenty minutes so at least the opportunity to get off and explore a little at every stop is there.


(Ps… tie your hair back if you decide to go on either the River Cruise or the open top Big Bus Tour, they don’t call it the ‘Windy City’ for nothing!)


We had another little look around the shops before having dinner that evening at Hamburger Mary’s in Andersonville. (If you’re staying close to or on the Magnificent Mile you’ll need to get a cab there – it’s about $20!)



Not only does Hamburger Mary’s have THE best cheeseburgers in town, there’s also a “Dining with the Divas” drag show every Saturday from 8.30pm!



In case you miss the 8.30pm show on Saturday, there’s tranny bingo on Sunday’s and Monday’s from 8pm!


And that brings us up to the end of Day 3!

For better insight into all the activities, cafes, bars and restaurants featured in the editorial above, watch my behind the scenes video from Day 1 – 3 here:

Stay tuned for Day 4 – 6 over the coming days!

Peaches x