Check out my Chicago city guide, featuring the best things to see and do, the must try food and a cool neighbourhood to stay in…

Chicago City Guide

Sitting proudly on the banks of Lake Michigan is one of the great American cities. Sorry Milwaukee, but I’m talking about Chicago…

I’ve previously written about travellers can expect on their first trip to Chicago. Now it’s time for the more substantive content – here’s my very own BurchAbroad Chicago City Guide, featuring things to do, where to eat and the best neighbourhoods to stay in… 

~ What to Do and See ~

Part One of my Chicago city guide covers my favourite things to see and do in the city… 

1. Take an architecture tour

One of the reasons I was excited to visit Chicago was its stunning and varied array of architecture. It’s a city which is synonymous with skyscrapers and, in fact, the world’s first skyscraper was constructed in Chicago. In case you’re wondering, it was the 10 storey Home Insurance Building. Although you won’t get a chance to see it in person because the building was demolished in 1931. 

Just north of the Loop, Chicago’s river is flanked by skyscrapers and criss-crossed by bridges. It really is an architect’s paradise. The best way to take all of this architecture in, is by a tour – walking or boat is best. The Chicago Architecture Centre runs a number of tours, which you can read about and book onto here. Not only will the tours provide you with an insight into the history of Chicago’s buildings, they will also provide you with some wonderful viewpoints from which to admire them.

Visiting Chicago - architecture and the US flag

2. Get High

Speaking of wonderful viewpoints, there is no shortage of views from upon high. The two most popular bird’s eye views of the city are found at the John Hancock Centre and the sky box in the Willis Tower (formerly the Sears Tower). Of the two, we preferred the John Hancock Centre. 

At the John Hancock Centre, you have two viewing options. The first is to head into the bar, grab a table by the window and enjoy a drink and the views. We arrived up for sunset – there was a bit of a queue at this time, so make sure you give yourself 20 minutes of so – and it was wonderful. We enjoyed a couple of cocktails, admiring the rows of light, below, which stretched out to the horizon under the last pink hues of sunset. 

Chicago City Guide - sunset at the John Hancock Tower

The John Hancock Centre also has a 360 viewing deck. The difference between the viewing deck and the bar, is that there is an entrance fee for the viewing area whereas entry to the bar is free (although once you factor in drinks, it works out about the same). Good news for photographers, Mondays are tripod friendly! Normally I would have been all over this, but I had stupidly broken my camera just before the trip and had to make do with my dad’s very old, basic Nikon.  I’m also not sure Lauren would have appreciated standing around and watching me nerd out with the camera for hours!

3. Visit the Rookery Building

The Rookery Building is one of Chicago’s landmark architectural masterpieces. The building dates back to 1888 and is the oldest standing high-rise in Chicago. The focal point of the building is its central light court, which was a particularly bold design at the time. The purpose of the light court is to allow natural light to flow into the interior offices. At the time the building was constructed, electric lights were only just on their way in, and the rental values of buildings were determined by how much light they received. The existence of the light court allowed the owners of the Rookery Building to charge higher rents (being a property lawyer, I particularly enjoyed this fact).

I booked onto one of the tours, which run on weekdays from 11am – 1pm. The tour guides are incredibly knowledgeable and bring the history of the building to life. The tour also allows access to the stunning spiral staircase.

4. See some live jazz

Chicago is well known for its live music, particularly jazz and blues. We were particularly keen to check out some jazz and headed for a night in the iconic Andy’s Jazz Bar, which is a must for any trip to Chitown. As we stepped in from the cold, a flurry of virtuoso saxophone notes provided a warm welcome. Our timing was perfect – two spots became available at the bar so we parked ourselves down and were treated to an amazing show. It’s definitely a cool date night location, although I may have overdone it on the mojitos. 

5. Check out Millennium Park

Millennium Park is one of the most popular tourist attractions in Chicago. People come to see the Cloud Gate sculpture, colloquially known as ‘the bean’, due to its shape. The curved contours of the mirrored sculpture create some really cool reflections. The bean, backdropped by a row of skyscrapers, made for one of my favourite photos from the trip.

Millennium Park’s other well known attraction is the Crown Fountain. It’s pretty weird and, visiting in the depths of winter, we didn’t get to appreciate its full effect. Two huge screens face each other, projecting the faces of a diverse selection of Chicagoans. In the summer it becomes an interactive oasis for families and visitors and water spurts out from the mouths of the faces (a reference to the traditional use of gargoyles in fountains). 

6. Enjoy an art museum

Chicago is home to a number of top class art museums. If you enjoy art, I’d recommend checking at least one out and, even if you aren’t the world’s biggest art fan, they do offer respite from the elements (it gets pretty chilly in the winter).

Chicago City Guide - Admiring the art in the Art Institute

My favourite museum was the Art Institute of Chicago, which could easily steal a half day away from you. I spent hours exploring the passageways and galleries within. It’s vast collection of art work is staggering and varied. I particularly enjoyed a temporary exhibit of Japanese masterpieces (I really dig Japanese art). The Art Institute is also home to the famous Chagall Windows, a dramatic wall of blue stained class. 

Chicago City Guide - Chagall Windows

In addition to the Art Institute, I also visited the National Museum of Mexican Art (definitely check out if you end up in Pilsen) and the Museum of Contemporary Art. The Mexican museum was interesting but I have to admit I found the contemporary art one very underwhelming – there wasn’t a great amount on show and I didn’t feel that it was worth the entrance price. 

7. Head down to Chinatown

When I head to a new city, I always love checking out Chinatown. We have a particularly thriving one in Birmingham and I was interested to hear that Chicago’s Chinatown is the largest in the United States. A walk through Ping Tom Park is worth it for some excellent views of Chicago’s magnificent skyline. Of course, the other thing that you can guarantee with a trip to Chinatown is mouth-wateringly delicious food for a reasonable price! The Chiu Quon Bakery and Qing Xiang Yuan Dumplings would be my recommendations (check out the food section, below, for more information).

8. Catch a sports game

If you like sports, Chicago has got you covered. It is one of a select group of US cities to host teams from the five major American professional team sports (baseball, football, basketball, hockey and soccer). Now, there are two teams which shine as beacons of sporting prowess: the Bulls and the Cubs. The Chicago Bulls were the basketball team of the 90s –  inspired to six NBA titles by the legendary Michael Jordan, before he joined the Toon Squad. Now baseball isn’t my cup of tea, but I do appreciate a historic sports stadium. Wrigley Field is home of the Cubs and dates back over 100 years to 1914. A pretty cool place to grab a few beers and try to enjoy the baseball! 

9. Visit the Chicago Cultural Centre

The Chicago Cultural Centre is both free to enter and focussed on the arts. There’s  an art gallery on the third floor and the building often plays host to free concerts. The Centre’s showstopper is its stunningly intricate stained glass Tiffany dome, which happens to be the largest in the world. 

Visiting Chicago - Tiffany Dome

10. Explore Chicago's neighbourhoods

Whilst a lot of the ‘must see’ attractions are in and around the downtown neighbourhood known as ‘the Loop’, don’t restrict yourself to this part of the city. Chicago is made up of 77 distinct neighbourhoods and I think its fair to say that away from the Loop is where you’ll find the real Chicago. I’ve already mentioned Chinatown, which was a favourite of mine. Wicker Park and Bucktown are the hip neighbourhoods, full of independent coffee spaces, boutiques and bars. We had an enjoyable night in Bordel, for its Vaudeville night (weekly on Thursdays), which is one of Chicago’s hottest burlesque shows. 

Chicago is home to the United States’ first officially recognised gay neighbourhood – the aptly named Boystown. Head to Pilsen for its plethora of murals and street art (and maybe a stop off at Cà Phê Dá to refuel – I’d recommend the Vietnamese sandwich and/or the chicken wings). You can also explore Wrigleyville on your way to see the Cubs.

But don’t rely solely on my list – make sure you do your own research and see what takes your fancy!

Visiting Chicago - out in the suburbs

11. Retail therapy

I can’t take a trip to the US without updating my wardrobe. I’m quite partial to Ralph Lauren and it’s waaaaaaay cheaper than on my side of the pond. We arrived just after Black Friday, and on the Sunday headed to the premium outlet mall, which is out towards the airport, to take advantage of the sales. Downtown Chicago is also home to North Michigan Avenue, known as the Magnificent Mile, which is home to just about every fashion shop you can think of. My only regret (aside from the following month’s credit card bill) is that I didn’t take a bigger suitcase!

12. Spy on Calder's Flamingo

Chicago’s financial district is home to a metallic monster – the world’s biggest flamingo. The statue’s vivid vermillion colouring is a stark contrast to the black glass of the surrounding office blocks. Definitely one to check out when exploring Chicago’s downtown area.

Visiting Chicago - the Flamingo

~ What to Eat ~

In part two of my Chicago City Guide, I’ll be focusing on classic Chicago dishes. Spoiler: it’s not the healthiest! The three pillars of Chicago’s culinary scene are the pizza, Italian beef sandwich and Chicago Hotdog. Apologies for the lack of photos – most of the time I’m so focused on finding food and devouring it that I forget to take a quick snap for the blog!


When it comes to pizza styles, give me a thin authentic Italian pizza over its deep pan American cousin every day of the week and twice on a Friday. That said, after spending the days exploring the sub-zero Chicago streets, a hearty Chicago pizza hit the damn spot. There are some battles where you have no choice but to pick a side and this is the case for Chicago pizza… Are you with the Jedi or the Sith? Marvel or DC? Team Edward or Jacob? In Chicago, the pizza power struggle takes place between Lou Malnati’s Pizzeria and Pequod’s Pizza. These long standing establishments are two of the leading lights in Chicago’s deep pan pizza scene. Now, I don’t wish to sway your decision, so my advice would be to try both and then decide which team to support.

Italian Beef

I had read that Italian beef was a must have when visiting Chicago. With a multitude of restaurants to choose from, I opted for the the classic: Al’s Beef. Al’s originates back to 1938 and the original location can still be visited in Little Italy / University Village.

So, you’re probably wondering, what’s an Italian beef? It’s pretty simple really: a nice, soft bun overflowing with thin, tender strips of beef. The beef is dry roasted in a secret marinade which dates back to 1938. Then add as much gravy juice and sweet and hot peppers as you desire. Simple, hearty and delicious. 

Chicago Hot Dog

Another key food group in Chicago is the hot dog. Chicago’s iteration it known for its numerous toppings – you’re looking at mustard, chopped onions, sweet pickle relish, tomato slices, a dill pickle spear, pickled peppers and a dash of celery salt. Tomato ketchup is a no-no (some places will not offer Tommy K at all), which I found particularly galling due to my love of the red stuff. That said, it didn’t stop me from trying one!

Other Notable Eats...

Chinatown: as I touched upon earlier, Chinatown is always a great spot for a bite to eat. During my wanderings, I fancied a mid-morning snack and popped into the Chiu Quon Bakery for a pineapple bun (always the sensible option). It offered me a brief flashback to Hong Kong. The bun was light with a sweet, crumbly top and washed down with a coffee to warm me up… It was -6 outside.

For lunch I opted for Qing Xiang Yuan Dumplings, for dumplings (duh!). The lamb and rosemary variety were particularly tasty and a unique flavouring compared with my previous samplings. They are one of the restaurant’s best sellers, and with good reason.

Wicker Park: our Wicker Park date night started with steak, rare and juicy (as it should be), before heading on over to Bordel for some live entertainment. Folklore is an Argentinian restaurant which, naturally, offers great steaks and red wine. 

For breakfast or brunch, be sure to check out Bongo Room, which sells some impressive plates of pancakes. If you’re looking for a coffee to wake you up / warm you up, the Wormhole Coffee, an 80’s themed independent coffee shop (it even has a DeLorean), is a good option.

Noble Square: despite their Mexican origin, tacos have become synonymous with US cuisine (similar to the balti in Birmingham). Naturally, we we had to sample some! El Barco Mariscos was a short walk from our Airbnb. We shared a selection of tacos and ceviche, which were reasonably priced and tasted great. 

Pilsen: as I said earlier, there’s a great Vietnamese place in Pilsen. At Cà Phê Dá, I’d recommend the Vietnamese sandwich and/or the chicken wings. They also do those fantastic Vietnamese coffees with the condensed milk.

~ Where to Stay ~

In the final part of my Chicago city guide, I’ll briefly be talking about where I stayed.

Because we were there for 7 nights, we decided to use an Airbnb. I find 7 days in the same hotel room a bit much! It also allowed us the luxury of being able to cook for ourselves and to chill out with a bit of Netflix when we’d had enough of the cold! We stayed in a part of town called Noble Square and I’d be happy to stay there again. It’s not one of those neighbourhoods, like Wicker Park, Buck Town or Pilsen, where people head to see things. It’s a bit quieter but without being too out of the way. There were great transport links to all the areas we wanted to see, a couple of local supermarkets/delis and an Uber was never too far away.

There you go, hopefully you’ll find this Chicago city guide useful when visiting. Hit me up in the comments, below, if you have any queries or own tips for Chicago.


Leave a Reply

Close Menu