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I absolutely love the USA but I’d never really thought too much about Chicago. I certainly never thought about a Chicago city break! Normally people from Europe want to visit US destinations like Orlando, L.A, New York or Boston. But so many of my friends have done J1s in Chicago or lived there and are completely in love with the city. I had heard so many great things about the Windy City that when I got the chance to visit I grabbed it with both hands. Here’s what I got up to with three days in Chicago.

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My Guide to a Chicago City Break

How to Get There – Dublin to Chicago

3 days in Chicago city break

Beautiful Chicago!

Chicago is easily accessible from Dublin with United Airlines offering daily direct flights from Dublin to Chicago. The flight over is around 8hrs and is closer to 7hrs on the way back. With American pre-clearance available in Dublin airport it makes it a very smooth process once you land in the US. You can read my full review of United Polaris Business Class from Dublin to Chicago  here.

A word of warning though, make sure you arrive in Dublin airport a minimum of 3 hours before your flight and don’t spend too long browsing in duty free; the queue for USA pre-clearance tends to be depressingly long. On my last couple of trips to the USA from Dublin the wait has been between 45 mins to an hour long and people who hadn’t budgeted their time properly were enjoying an extremely stressful start to their trip.

From O’Hare there’s a train that brings you right into central Chicago. The Blue Line train is located in Terminal 2 and takes around 40 minutes to get to Downtown Chicage and runs 24hrs. A single ticket costs $5.00 or you can buy day passes of various lengths for a reduced price. For example a 1 day pass costs $10.00 and provides you with unlimited ues of CTA buses and trains for the day. You can even buy a Ventra card, which is a lot like the Oyster card in London, and just top it up as you go. HANDY! Of course, there are other ways of getting from the airport to the city centre, such as taxis or private hire cars (we used Windy City Limos), but be warned that Chicago traffic is rough. 

What to Do and See in Chicago

In Chicago there is something for everyone to enjoy, 24/7, every day of the week. You’ll never be bored in Chicago.  Here’s a list of some of my favourite Chicago sights and attractions.

3 days in Chicago city break

Buildings everywhere you look!

1 – Chicago Architecture River Cruise – I cannot recommend this enough. The Chicago Architecture Foundation Centre River Cruise aboard Chicago’s First Lady Cruises, as it is formally known, is something not to be missed. I’m not particularly interested in architecture, but my mam’s an engineer and I studied art history for a while so I have an appreciation for art and beauty mixed with maths and physics, especially when it’s on such a skyscraping scale. Regardless of your level of interest in architecture you’ll find this river cruise absolutely fascinating. Jaw-dropping views of the city are also guaranteed so have your phone/camera ready. The tour lasts around 90 minutes and tickets can be booked online or bought at the dockside ticket booth, I recommend booking in advance as it fills up quickly. You can read more about the tour here

2 – Classic Lake Tour – I LOVED this. Lake Michigan, one of the Great Lakes, provides Chicago with what feels like a coastline. This 40 minute tour with Shoreline Sightseeing boasts stunning skyline views of Chicago as well as sprawling views across the expanse of Lake Michigan. You genuinely feel like you’re out at sea, it’s very hard to believe that a lake could be so vast. You can get up out of your seat, wander around the boat and even purchase snacks and drinks on board. The views of Navy Pier are fantastic. I’d highly recommend it. READ MORE AND BOOK HERE.

3 days in Chicago city break

The view from the lake cruise. Look at the skyline.

3 – Navy Pier & Centennial Wheel – Originally dating back to 1916, Navy Pier is 50 acres of pure Chicago landmark goodness. It is free to enter and walk around but tickets must be purchased for attractions. On Navy Pier you’ll find attractions such as the Chicago Children’s Museum, the Centennial Wheel and Chicago’s Funhouse Maze. There’s also an IMax theatre and a lovely public garden area called the Crystal Garden. If you’re after a meal there’s no shortage of food stalls and restaurants on Navy Pier. It’s a great place to spend a lazy afternoon. 

4 – House of Blues Gospel Brunch – This was such an incredible experience for me, something truly American that I’d never seen the likes of in Ireland. It was absolutely fantastic. You are welcomed by a breakfast buffet full of things like fried chicken, biscuits and gravy and waffles with cream. Once your plate has been loaded up you grab a mimosa before taking your seat. Then the show begins! The show itself is fantastically entertaining and surprisingly energizing. Crowd participation is expected so be prepared to be up on your feet dancing, clapping and singing along. Top tip, there’s a huge second buffet at the back of the room that isn’t really sign posted but it has all the good stuff! So, avoid the queues at the omelette station and wings buffet and just head straight to the back. They do two shows every Sunday at 10AM and 12.30PM. You can book tickets HERE.

3 days in Chicago city break

The view from Lincoln Park.

5 – Lincoln Park – Apparently not the same as the band, Linkin Park, but a great park all the same. This lakefront park is home to Lincoln Park Zoo, which is FREE to enter. They do accept donations but they are not compulsory! The park also houses Lincoln Park conservatory and the Chicago History Museum. The park itself is over 1,200 acres of green and is the perfect spot for a picnic. If you’re on a budget you could definitely spend a day exploring Lincoln Park without spending much money at all. 

6 – Wrigley FieldWrigley Field is the famous baseball field in Chicago. It doesn’t matter if you understand the sport or not, sports games in America just have an incredible atmosphere. Book yourself a ticket, grab a hot dog, take a seat and soak up the Americana of it all. It always makes me feel like I’m in a movie. We watched Chicago Cubs Vs Cincinnati Reds and I didn’t really have a clue what was going on, despite it being suspiciously similar to the game of Rounders. But I LOVED the buzz in the air and the excited yells of die hard fans who have been supporting the same team for generations.

3 days in Chicago city break

Cheering on the Chicago Cubs.

7 – BIG BUS tour – These tours are always great if you have limited time in a city. They enable you to see a lot in a short space of time and you can hop on and off as you please. Stop at landmarks such as the Hancock Center, Willis Tower, Wrigley Field, Shedd Aquarium and more. Book your BIG BUS tour HERE.

8 – Sky Deck Chicago – Want a birdseye view of the city? Then make sure to visit Sky Deck on the 103rd floor of Willis Tower. They have these glass boxes, called The Ledge, that extend over the city so that you feel like you’re floating about the city. 1,353 feet above the city to be precise. It’s definitely not for those with vertigo or a fear of heights. But if you don’t suffer from either of those conditions then you’ll love it. The views are stellar and the photo opps are endless. You can see for up to 50 miles and you can even see 4 states! The queue does get quite long though, so make sure you get there early. 

3 days in Chicago city break

Floating above Chicago in glass box.

9 – Catch a Blues Show – Chicago has some incredible Jazz and Blues clubs. If you’re into music try to catch a show at one of the clubs. Kingston Mines is the largest and oldest Blues club in Chicago and definitely worth a video. Winter’s Jazz Club has live Jazz shows 6 nights a week and is a small intimate venue. 

Some other tours/attractions you should check out if you’re visiting Chicago:
90 Minute Mob and Crime Bus Tour
Chicago Day Time Helicopter Tour
The Chicago Bean/ Cloud Gate at Millenium Park


Shopping in Chicago

Chicago is a great city for shopping. I picked up plenty of bargains over there. The Magnificent Mile, North Michigan Avenue, is the main commercial shopping street. It has high street shops, luxury retailers, restaurants and more. You could definitely spend an afternoon assaulting your bank balance on this street. If you go to the Starbucks on the top floor of Uniqlo it has incredible views of North Michigan Avenue from above. There’s a great TJ Maxx just off North Michigan Avenue as well, I got myself some lovely Calvin Klein bits in there.

If you prefer something a bit more boutique Wicker Park is a great area for independent shops and their Farmers Market is full of tasty fresh produce. It feels a bit more “authentic Chicago” here. There’s plenty of brightly coloured street art sprinkled through out the neighbourhood too if you’re not that interested in shopping.

If it’s outlet shopping you’re after there are a couple in Chicago. Fashion Outlets of Chicago is popular mainly due to its excellent location and decent selection of brands. It’s only 5 minutes from the airport so it is perfect for some last minute shopping before you fly home, or for stop over shopping. Chicago Premium Outlets is further out of the city, nearly an hour on the train, but the shopping experience is superior with a wider variety of brands. 

Where to Eat/Drink in Chicago

3 days in Chicago city break

Lou Malnatis,a Chicago legend.

No Chicago city break is complete without A LOT of food. Lou Malnatis is a Chicago pizza institution. There are several around the city. I visited the one at 1120 North State Street. Chicago deep dish pizza is something every visitor to Chicago must try. I remember liking the Pizza Hut version when I was a kid but I hadn’t tried it since. I got an individual classic margherita deep dish and it was delicious. It was, of course, filling but definitely worth trying. Their thin pizza was also extremely tasty, but that’s not the true Chicago experience! A word of warning, their starters are HUGE. I had the cheesy garlic bread and it was basically an entire baguette. 

If you fancy a big breakfast in a down to Earth diner then check out the Eggsperience Cafe on West Ontario Street. Their menu is extensive, their portions are huge and their food is absolutely delicious. I had the breakfast chilaquiles which was tortilla chips with green salsa, mozzarella, two eggs, refried beans, sour cream, lettuce and tomato. I couldn’t finish it but I’ll be dreaming about it every morning for the rest of my life!

3 days in Chicago city break

The best breakfast I’ve had in years.

For lunch check out the Revival Food Hall. This is a sort of up market food hall that mainly caters to local office staff. You can get anything from Poke bowls to burgers. I got a grilled cheese and pickle sandwich from Danke which was extremely tasty and a salted caramel cookie from the HotChocolate Bakery. The burgers from the Fat Shallot looked incredible. There’s no shortage of options and all dietary requirements are catered to. 

If you need a snack while you’re sightseeing make sure to try a Chicago-style hot dog. The Chicago version of a hot dog is a beef frankfurter on a poppy seed bun topped with mustard, chopped white onions, bright green sweet pickle relish, a dill pickle spear, tomato, pickled sport peppers and celery salt. If you want all the toppings you ask for it “dragged through the garden”. Don’t dare ask for ketchup on it or you’ll be cast out of Chicago!

3 days in Chicago city break

The lovely Frosé.

If you’re looking for a classy cocktail with a city view check out the rooftop bar at the Dana Hotel. They have a cocktail called the Frosé which is basically a frozen Rosé cocktail which I suspect also has some other spirit in it because it’s VERY strong. It is really just the kind of place for one drink though, the prices are high and the majority of the clientele are young posers.

Where to Stay in Chicago

3 days in Chicago city break

The gorgeous reception of the Dana Hotel.

3 days in Chicago city break

My room in the Dana Hotel.

During my 3 days in Chicago I stayed in the Dana Hotel. It’s a funky design hotel in the city centre, just minutes away from The Magnificent Mile. The location really is perfect! The lobby is beautifully decorated with sculptures and oddly shaped furniture. There’s a restaurant on the ground floor and a bar on the first. The rooms remind me of a sort of sexy, sleek office. In the rooms robes and slippers are provided along with a YOGA MAT (the first time I’ve ever seen that in a hotel!). 

3 days in Chicago city break

Love those floor to ceiling windows!

They have, unfortunately, adopted that awful trend of having a glass wall between the bedroom and the bathroom so that you can gaze lovingly at your other half while they sit on the toilet. Le sigh. I will give them points for putting a curtain across it though so that you can preserve some modesty. My favourite thing about the room is that the windows are floor to ceiling so that you have an incredible view over the city. The Wi-Fi is great and the TV has plenty of channels. The staff are incredibly friendly and helpful and will always wish you a good day. 

You can read more about the Dana Hotel here.

Have you been to Chicago? 
What did you think?

*I was a guest of United Airlines and Choose Chicago on this trip. However, all opinions are, as always, my own.*

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One Response

  1. Kevin

    thanks for the great article on Chicago, we’ve also stayed at the Dana hotel – sheik little boutique hotel, and close to some good eateries!


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