Chicago downtown

Chicago Film


Eight years ago I boarded a plane from London’s Heathrow airport, heading for the United States. Offered a job in either Houston or Chicago (and knowing a little of Houston), I chose the windy city as my new home and swiftly purchased three travel guides from a local bookstore. 

Having visited the US as a teenager and then twice more in my twenties (on huge road trips), somehow I had still never entered its city limits, and I found myself feeling altogether ignorant of this midwest behemoth. What did I know of the place? It has a musical… something about Al Capone? Does everyone have so little knowledge of this city?

The answer, from the perspective of foreigners, is yes. This city is simply off the radar in the minds of Europeans. As a young Brit, I grew up learning about New York, Los Angeles and San Fransisco via endless television shows and Hollywood blockbusters. I’d heard of Boston in history lessons and visited Florida on standard childhood Disney pilgrimages. Chicago however, lay dormant, in a tourism black hole, never spoken rudely of, but never seeking attention either. 

CHICAGO cityscapeAs I began my pre-emigration research, I began to get excited at just how amazing the city appeared. Home of the skyscraper? World famous cuisine? Hang on… a beach!? 

I found out more and more, everything I read or watched got me more excited, and like that odd experience when you learn a new word, I began to hear it everywhere. I saw it on tv, it appeared in a Batman movie, the president was born there! How had I not known more about this place already?

On August 13th 2010, on a hot, clear-skied Friday evening, I touched down at O’Hare airport for the first time. A lot has happened since then, far too much to discuss here, but eight years later, as I pack to move to Thailand and leave this place for good, it seems like a moment for reflection, and to impart some of what I have learned about his magical city, (the best in the US in my humble opinion), to others who are as bereft of Chi-town knowledge as I was all those years ago. 

CHICAGO with park foreground

Here is our Chicago guide for the unwitting, accidental visitor, to prep you for the biggest surprise in the United States. We include maps for activities, highlights, and some secrets that only a local can supply!



Route map for Chicago by richard howland on

 What you Need to do:

Start at the John Hancock Building. This is one of Chicago’s most iconic skyscrapers, and without a doubt the coolest one to visit. Unlike the Willis (formerly Sears) Tower, which is tallest, it doesn’t have overpriced entry fees and awful views. The lookout from the top of this feat of engineering is without question the best view of the city you’ll find. 

To get the most from your visit, dine in the restaurant (not much competes with eating great food while looking out at Lake Michigan from 95 stories in the air. If you’re not hungry, just grab a cocktail and watch the crazy sunset.

The Bean/Cloudgate

Okay, I know, its just a big shiny thing. Wrong. I’m afraid you’re just going to have to trust me. I’ve sent every visitor from out of town to the iconic bean, and no one has been disappointed. Not only is it crazy to look at in person (its so much bigger than you think), the reflections of the city are cool, you’ll be taking selfies of your warped reflections for longer than a person should, and right next to it is one of the coolest water features and most amazing parks I’ve ever seen!

CHICAGO the beanNorth Beach

Aright, why should you visit Chicago? You want a beach vacation! That’s fine, we have you covered. Yes, Chicago has beaches! In fact, there are twenty-four beaches in Chicago! I’ve labeled this section under North Beach, but it really depends what you’re after. If you want tourists, ripped athletes playing volleyball and a general feel of unworthiness, this is your beach.

CHICAGO north beach summerI do tend to prefer to go a little north of this beach (up near Diversey, or even Montrose beach), where things are much quieter. Regardless of which beach you chose, you’ll find sand, hot sun and waves (yes waves) with the added bonus of having no salt in the water!

Wrigley Field

If you’re coming to Chicago, know that sports are a big deal, this is the home of Jordan, of the Cubbies, and more recently the dominant Blackhawks hockey team. People here take their teams passionately seriously, and you’d be remiss if you didn’t get involved. 

Wrigley Field is a baseball icon, its quintessentially American in every way possible, and regardless of your feeling towards this sport, it’s a great day out. Sunshine, music, hot dogs and beer. It’s a whole lot of fun. With the turnaround by the team of recent years (they won the championship for the first time in 108 years just two seasons ago. Plus the new stadium and surroundings are a carnival of bars, cafe’s and fun dining experiences, you could spend a whole day in Wrigleyville. 


Much like the Cubs, seeing a Hawks game for the first time will change your perception of hockey, while feeling more like a Chicago party than a sports game. When the hawk score, you’ll see what I mean. The stadium is pretty huge, but the views are great from every angle, and it’s a really exciting game to see live, 3 hours go by in minutes and you’ll be buying a jersey on your way out, an honorary Hawks fan. 

CHICAGO river viewLou Malnattis / Peaquods

Chicago is known for its deep dish Pizza. Trust me though, not all deep dish is created equal. The two standouts are these pair. Lous’s I’ve ordered tons of times (too many), and the deep dish special is something to behold. Peaquods at it’s best is equally amazing, but I’ve had good and not quite as good experiences. 

Lou’s will convert you, it’s so fresh, so tasty and honestly, you’ll never finish a whole pizza. Upon my arrival I tried a few deep dish pizzas and hated everyone, I’d refer to them as tomato pies. It turned out I’d just gone to the wrong places, so now you know!

The Burger Bar

So many great, out of this world, great great burgers to be had in this city; Dryhop, Dukes, Kuma’s Too, DMK to name a few (Wilde’s if you want an incredible buffalo chicken burger), but for me, the Burger Bar wins out. The array of burgers on offer, from poached apple to pork belly, Asian fusion to ribs, all atop a superbly cooked patty, with a great beer selection to add. This place is relaxed but cool, in an easy location and never fails to please. That being said, if you find yourself walking by any of the places mention above, walk inside, they are all superb. Just wow. 

Mag Mile Shopping

Every guidebook will talk about this as an essential experience, I don’t fully agree. I toyed with leaving this on the ‘what you can miss’ list for a while. In the end, I’ve kept it here, but for two reasons. The journey along Michigan Avenue takes you through some of the most iconic aspects of downtown Chicago. You’ll start at the Hancock building, walk down (through a hoard of other tourists) past the Wrigley Building, the Tribune Tower (which has bricks and stones from all over the world, and beyond, built into it) and end up at the beautiful river walk. Secondly, most visitors like to buy some Abercrombie or Hollister clothes when they’re here, and you find them along your way. Stop for a meal in Bandera’s about halfway down.

Lakeview Shopping

A much nicer and far more enjoyable experience, in to head up to the Lincoln Park/Lakeview area and stroll around. There are more cute shops, lovely cafe’s and bakeries, amazing bars and restaurants and fun activities in these two neighborhoods than anywhere else in Chicago. Every street yields yet another set of options to look at. Stores like Four Sided will sort you at with trinkets and crafty home goods and Climate for quirky art and products all things Chicago.

CHICAGO lincoln park zooBreweries 

Well, where do we start here? The craft beer scene in the states has exploded in the last ten years. We’re at a point now where that pretty much all we buy. There are literally thousands of options, and every state,  every city has its unique selection of fantastic breweries. Chicago is no different. In fact, its up there with the best of them. 

With so many to mention its hard to limit this, and with the speed of development in the industry things will change fast but… here are my top picks.

Maplewood, with its amazing IPA’s, has a great taproom, worth the cab ride and you could easily accidentally spend a full day sat in here. A great atmosphere, awesome food and a fun location (its hidden away in an old industrial area). 

Half Acre is just superb. With two locations, you can easily sample their stuff, but head to the Balmoral location if possible, it’s a big site, has tours at 11am on weekends which are phenomenal. We had the most informative talk and four superb fresh pints and a souvenir glass for $10. These guys make some amazing beer two, so stop in, sample a few and enjoy there new little restaurant area as it’s exquisite. 

Revolution has been a staple for a long time. Another big local brewer, they have a really cool site, with an all-American, barrel filled hall for you to sit, drink and munch pizza in. With a very wide range of beers, they will definitely have something you’ll end up carrying out. 

Off Color is my final pick, mainly because they are so very different. As the name suggests, they are all about making unique tastes, I’m not going to say more, but head to there Lincoln Park location and get ready to be surprised!

CHICAGO neighborhoodBrunch

Not so much a meal as an event in Chicago, this is the city’s main meal of the day. Really, it’s a big deal. The majority of Chicago’s populations can be found enjoying this important ritual between 9am and 12pm every Saturday and Sunday (not that people limit themselves to weekends). The choices of location and menu are almost infinite, but here are my top picks:

Hash House A Go Go: This place is known for its breakfast sage chicken, and known even more for its sizes. These are the meals, we’re talking everyone gets their camera out, large. A great atmosphere greets you, absolutely delicious and very unique. 

Sip: Found in Uptown, this trendy Jazz themed restaurant/bar/music venue served an outstanding brunch menu, and with $15 bottomless mimosas while the jazz plays away, you might be here a while.

Yolk: A chain in Chicago, started downtown in 2006, this place does good work. A huge menu is its biggest draw, but pretty much everything tastes good. 

Wishbone: A quirky, fun little place, they say they are taking a healthier approach to southern cooking, I just think its sublime. Some twists on well known southern comfort food make this place another unique food experience. 

Crosby’s Kitchen: Nothing overly quirky or unique about this place, its just really, really good! Try their hash brown, its a creamy take on the typical breakfast potato special. 

Architecture Boat Tour 

I know what you’re thinking, but I promise this is epic. The history of Chicago is cemented into its buildings. The city that invented the skyscraper has a crazy amount of unique buildings, it’s definitely one of the prettiest cities. All the fun facts aside, you get a boat ride down the river, and then some companies will take you along the city front on Lake Michigan. Very fun couple of hours. Make sure you take sunscreen, with the wind in your hair it’s easy to forget you’re burning, I’ve been there, it’s not fun at all!

What you can Miss:

1. Willis Tower: Sacrilege? Maybe, but as someone who’s been here a while, I can say wholehearted, it’s not worth the $35 fee. The view, due to the tower’s position is not even close to the Hancock, or even Trump Tower’s view. They have the whole stand on glass gimmick, but the Hancock has the ‘Tilt’ which is basically the same experience. Add to that food and cocktails in the Hancock and nothing but some posters to look at in the Willis, and its a no-brainer. 

2. Navy Pier 

Yep, another one which the guidebooks will send you to, not sure why. I mean look, its a long Pier, you’ll stroll like a sardine in a packed crowd, pass 20 souvenir stands, get to the end and turn back. I don’t know anyone who goes there by choice. The one thing it does have going for it, it Saturday and Wednesday nights they release fireworks, a good display, all summer long. Find a spot nearby on the beach to watch it!

3. Bears

There are 3 other sports to go see, all more fun, way cheaper (you can find a bulls/hawks/cubs ticket for $30), a Bears game will set you back around $160 minimum. It’s a joke. Plus, right now they aren’t anything special to watch, I love them, I’ve been, I wish them well but as a one time visitor, unless you’re a big football fan, see one of the other sports. 

4. Chinatown/Little Italy

I’m not going to limit this to one area. I once went searching for ‘little Italy’ it certainly is little. I couldn’t find it. Plenty of Irish bars around that area though. 

Chinatown is a little more obvious but is sooo small and underwhelming, it’s not like London or New York, its a street, with a few restaurants. Better food can be found in other neighborhoods. 

CHICAGO fountain

Chicago Buckingham Fountain

Explore The Neighborhoods:

Too many people visit Chicago and stay in the downtown area, never venturing out. It’s insane. I would say 90% of Chicago’s “best bits” are out of the Loop. This is a city of fun neighborhoods, and exploring them is the avid traveler’s main goal. You won’t have time for them all, so let’s go with the top few. Be sure to walk around Lakeview & Lincoln Park. This IS Chicago. Between them, you have the cities best food, the best beaches, best quaint stores and boutiques, best cafe’s, the best parks and the city’s zoo (free to everyone). This should be where most of your time is spent. 

Wicker Park is Chicago’s hipster hangout. Tight jeans, beards and tattoos are everywhere, but so are great places to eat and drink (Mindy’s Hot Chocolate is a world of alcoholic and non alcoholic hot chocolate creations to die for), shop for funky clothes or vinyl records and of course, people watch. 

Pilsen just recently made Forbes top ten neighborhoods to visit…in the world! Yep, Chicago’s Mexican neighborhood is a visual and culinary feast. 1970’s murals decorate buildings everywhere you look (as do tourists with selfie sticks in front of them), performance studios, trendy bars and National Museum of Mexican Art are the main highlights, but honestly, just walking around and enjoying the street art is fantastic enough. 

CHICAGO millenium parkTransport:

Getting around this city is cheap. The local transport authority (the CTA) run buses along every street, and the Chicago under/overground trains – the El, will get you to any of the places mentioned here in minutes. You can hop on and ride for 2 minutes or 2 hours for a mere $2.50. Aside from that, Uber dominates here, grab the app and zoom around, and finally, walk! Find the neighborhood of the day and stroll, that’s the best part!


Late May to September. That’s it. No really. The summer is hot and gorgeous, you could just lay on the beach every day, but outside of those months?… I’ve seen it hit -40 degrees. Don’t risk it!

That’s Chicago! A city full of activites, great hot summers filled with street festivals and beach parties, don’t be fooled into missing it from your American vacation, it should be top of your list.

Keep Traveling,




Chicago 3 images, cityscape