• Roxii Hoare-Smith

10 reasons to visit Chicago

Updated: Dec 28, 2019

Chicago is one of the largest cities in the US and a city where you need to arrive with an appetite for art, architecture, sports and of course, food. 

As the Windy City will blow you away with its deep-dish pizza, beautiful buildings and stunning skyline. 

So here’s 10 reasons why you need to plan a trip to Chicago ASAP. 

1. For the Food

You cannot visit Chicago without sampling its signature deep dish pizza. This indulgent dish may seem excessive with its stringy mozzarella, rich tomato sauce and golden crust – but its a must-have. Giordano’s and Lou Malnati’s are the classic choices for deep dish and have a variety of locations across the city and the suburbs. 

The deep dish pizza comes in a variety of sizes with a variety of fillings (it is more like a pie than a pizza!). We went for the pizza for 2 people which was way too much for us as it’s SO incredibly filling. 

Try Chicago’s most famous hot dog at Portillo’s. Portillo’s was founded by Dick Portillo who was serving his Chicago-style hot dogs out of a trailer back in 1963, now there are branches located all over the city. This no-frills joint is now a Chicago staple and worth the lengthy queue. I’m not a big hot dog fan but these were incredible!! 

But if you get homesick then there’s always Nandos… 

I must admit I am a huge Nandos fan. I could eat it every day (as long as it’s drenched n lemon & herb sauce). So we checked out the one in Chicago as it would be the only one we would come across during our 9 week trip so we wanted to have our last Nandos for a while. It was a bit disappointing, I got my usual chicken thighs and the dish came half the size of the ‘UK version’ and the lemon & herb sauce and macho peas tasted way too sweet and sugary! 

Nandos is located on 953 W Randolph St. Below Nandos there is also a Nutella cafe which looked amazing!

2. For the Art and Architecture

Art Institute of Chicago is top-ranked in the world by TripAdvisor (and has been for four years in a row). Here visitors can view the greatest Impressionist collection outside of Paris. They offer free tours each day at Noon.

Take an architecture tour along the river which is loved by both tourists and locals alike. Tours are held during the day or at twilight. Photographers can embark on a Chicago photography cruise to get the best shots and enjoy a cocktail while admiring the views on a luxury boat. 

3. For the views at Skydeck Chicago

Head 103 floors up the Willis Tower for Chicago’s Skydeck which offers panoramic city views plus the opportunity to see up to four states. If you’re brave enough you can venture out onto The Ledge – a glass floor balcony 103 floors above Chicago – for that perfect photo opportunity. 

The views were so fantastic and the glass floor was the perfect photo opportunity!

4. For the TILT at 360 CHICAGO 

Experience further views of the windy city’s skyline and beaches 1000 feet up at 360 CHICAGO. If you’ve managed to go onto The Ledge at the Skydeck then anything else is a piece of cake. Embrace the opportunity to view the city on The TILT. The TILT is Chicago’s newest thrill attraction – it extends out and over The Magnificent Mile and offers downward facing views plus as stunning outlook of Chicago’s skyline. 

The TILT costs $7 extra to go on and lasts over a minute. It’s an awesome experience!

5. For the Shedd Aquarium 

Aquariums aren’t really my thing, I’ve been to the London aquarium countless times so I’ve never usually interested in visiting any other. BUT this isn’t just any aquarium. Shedd Aquarium is one of the world’s largest indoor aquariums and is home to 32,000 animals including belugas, sharks, tarantulas, turtles, dolphins, penguin and frogs. 

The aquarium offers visitors an opportunity to touch the sting rays (which we did, it was so fun!), sturgeons and sea stars and watch the beluga whales, sea lions, and dolphins during feeding time. It was so fascinating! 

You can also enjoy great views of Chicago’s skyline from this part of town. 

Please excuse my hair which had been attacked by the wind. It’s not called the windy city for nothing!

The above attractions are covered in the Chicago CityPASS which offers 53% discount on entry prices plus VIP entry at most attractions so that you can skip the queues. 

6. For the Magnificent Mile

Walk Chicago’s famous The Magnificent Mile which offers something for everyone. From five-star hotels to upscale and purse friendly restaurants plus luxury and high street fashion stores. My favourite places along The Magnificent Mile had to be The Cheesecake Factory and Ulta Beauty.

This strip is also home to historic Chicago landmarks such as the Chicago Water Tower and John Hancock Center (now 360 CHICAGO). 

7. For the Suburbs 

Or the ‘Burbs as they say…

Venture out of the city and experience the wonderful communities of Chicago, there are over 77 of them! 

Logan Square is known as Chicago’s hipster haven and it is the perfect area for cheap eats. For traditional American fare try Bang Bang Pie shop, a rustic bakery which specialises in grits, biscuits and the best pies you’ll ever try. 

I’m not a Key Lime Pie fan but this pie completely changed my opinion and I couldn’t get enough. I don’t think a Key Lime Pie will ever compare now!

American biscuits (left) aren’t the usual biscuits we are used to! These type of biscuits aren’t as sweet and is savoury and are more similar to scones. Grits are slightly like porridge but savoury – my favourite was cheesy grits!

The Chicago Greetings Tour mural is also located in Logan Square, close to California station, for that postcard perfect shot. Although there is the risk the mural could be covered up by parked cars, but like me instead you can get a ‘Greetings from Chi’ photo…

Wicker Park is close to downtown Chicago and a great spot if you are looking for live music, buzzing nightlife and top-rate food, as this area is home to some of Chicago’s most sought after tables. If you’re a shopper then you’ll love this part of town for its independent boutiques and vintage shops. 

For a quiet and calm hideaway – Lincoln Park is the answer. As well as beautiful scenery, Lincoln Park is home to Lincoln Park Zoo which is one of few free entry zoos in the country. While your there take time to check out Lincoln Park Observatory and Cultural Center. 

8. For the bars in Wrigleyville

If you are visiting during baseball season and can’t make it to a game then head down to Clark Street and soak up the atmosphere in the Wrigleyville bars. We popped by when the Cubs were playing the LA Dodgers in the World Series and the atmosphere was fantastic!

There’s the iconic Cubby Bear for live music and day drinking and Casey Moran’s for five full service bars – so you’ll never struggle to get served – plus a beer garden and rooftop. 

Check out Sluggers World Class Sports Bar for over 30 TVs, 10 6ft projection screens and a sports area with batting cages, air hockey, skee ball and a pop-a-shot basketball toss. Be prepared for rowdy crowds but unbeatable atmosphere you won’t find elsewhere in the city.

9. For The Bean

During a visit you must get that all important photo next to the Bean in Millennium Park. The Cloud Gate Sculpture (aka The Bean) is made of 168 highly polished stainless steel plates and offers a great reflective view of the beautiful Chicago skyline. It’s free to visit and we found that it was best to go before 5pm between Monday to Thursday when it’s less busy. 

10. For the beer and cheese in Milwaukee

Just a 2 hour drive, train or bus ride away is Milwaukee, Wisconsin. Squeeze in time for a day trip – especially you are a beer or cheese lover – and tick off another state.

Milwaukee Public Market is the perfect place for a gourmet feast with its large selection of local vendors, food counters, restaurants, bakeries and even a wine bar. You can’t leave Milwaukee without tasting cheese curds – these mouthwatering delights are best enjoyed breaded and fried. I miss Wisconsin cheese curds so much. They were definitely one of my favourite dishes I tried on the trip!

Unfortunately there were road works during our visit so this photo isn’t the best!

Visit the home of PBR as Pabst Milwaukee Brewery and Taproom is located in downtown Milwaukee. Take a stroll to Best Place at the Historic Pabst Brewery where you can learn about the history of Pabst. Before our visit to Milwaukee I hadn’t tried Pabst Blue Ribbon but I fell in love. I’m more of a wine or gin drinker and always avoid beer but America has changed my opinion! PBR may be described as hipster beer or as some American’s call it ‘liquid s**t’ but I loved it and it’s a great beer to start off with if you are a newbie like me. If only we could buy this in bars in the UK…

Today we visited Milwaukee, Wisconsin. Another state to tick off 🇺🇸 We went on an amazing brewery tour at Lakefront Brewery (which was absolutely hilarious!) and we also visited Milwaukee Public Market (which I am sure I recognise from Bridesmaids 😂🙊?!). Thank you for showing us around @ruddly22 and for putting up with my excitement over school buses and Kool Aid 😂🙊A post shared by Roxii Hoare-Smith 🦄 (@studdedkissesblog) on Oct 19, 2017 at 9:56pm PDT

Stop by Milwaukee’s spy bar – Safe House – located down an alley way with an unassuming entrance. This place is like a tardis, it is absolutely incredible and unlike anywhere I’ve ever been before. You’ll need a password to get in though but don’t worry if you don’t know it though. All will be revealed after completing a task on arrival!  

Milwaukee is home to a great selection of breweries which offer tours, but if you are looking for a tour which offers a generous amount of beer and will have you doubled over with laughter then go to Lakefront Brewery. You also get a lot of beers included with your ticket (as well as a glass to take away) and their cheese curds are insanely good. 

Where to stay

We booked a private room on Air B&B in the Wicker Park and Ukrainian Village area. This was a great area as it felt really safe, there were great bars and restaurants and it was a lot cheaper than staying downtown. We used Uber Pool to get around so it was cheap to go downtown and also super quick. 

How to get there

We travelled to Chicago but Amtrak from Cleveland, Ohio. The train takes around 7 hours although ours got delayed so we got to Chicago 4 hours later than we were supposed to. The trains in the US aren’t like what we are used to in the UK, they don’t run very often which meant we had no choice but to catch the train at 3.45am (EST) from Cleveland which was due to get in around 9.45am in Chicago (CST). I absolutely loved taking the train as you get so much leg room and the seats recline far back so you can line down and sleep, it’s much more comfortable than flying! We got talking to a lovely Amish family at the station in Cleveland. It was so interesting sharing stories and traditions with each other about our daily lives. 

When leaving Chicago, we travelled by train from Union Station to Memphis. Before boarding our train we got interviewed by The Daily Show with Trevor Noah! So you never know what you’ll come across at the station in Chicago.

I originally wrote this article for HuffPostUK which can be viewed here.

Just arrived in Memphis, Tennessee after a 10 hour train journey from Chicago. Felt a bit sad leaving Chicago, I really loved it there. In some ways it really reminded me of London! 🇺🇸🇺🇸🇺🇸🇺🇸🇺🇸🇺🇸A post shared by Roxii Hoare-Smith 🦄 (@studdedkissesblog) on Oct 21, 2017 at 6:19am PDT

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