Why Chicago should be the next city you visit in the USA – even if it was also the last

Skyline at night from boat

Before we get into this, Noo Yoikers, I do understand. You find it hard to believe how anyone – and a Limey at that – could rate another city over yours. Don’t get me wrong here; I love the Big Apple as a wealth of articles on this very site will attest. But for my money, the Windy City (you guys sure do love nicknames) has you beat. I know I’m not going to be able to convince you, but give me the chance to convince everyone else before unleashing virtual hell, okay? Thanks.

Let’s start with a little background info: I came very late to the USA party. I mean I was over 40 before I set foot over there – not because of a lack of interest, more due to getting sidetracked by the attractions of Europe, Africa and having a family.

I documented my first impressions of New York and the US in general after that initial trip to the city that actually does sleep now and again, if rather fitfully. And I have no doubt that everyone should visit New York – it’s an amazing city. Actually I think that’s why Chicago made such an impression a year later – it was even better. Whether you visit for a short city break or stay longer, Chicago will steal your heart.

How do you top a city so good they named it twice? With a city so sure of itself that they didn’t need to. Both cities are loud and proud, but whereas New York shrieks, Chicago merely raises its voice.

Before all of you who heart NY feel compelled to throw a bagel at me in protest, remember I heart NY too. And it is possible to love both just as much for different reasons; as well as Miami, San Francisco et. al.

But Chicago is best.

At least 28 reasons why Chicago is the greatest city in the USA if not the world

Just look at it – look at that skyline. And the water!


Beautiful, huh? What a combination – skyscrapers, a huge green waterfront strip, sandy beaches within cycling distance of downtown and water that looks like it should be in the Caribbean. But it’s a lake. One so vast that Chicago feels like a coastal city despite being slap bang in the mid-West.

People are friendly and you can hear yourself think

Unlike the folk in many big cities I could mention, Chicagoans are a friendly bunch. Perhaps even more importantly, they function at a reasonable speed, rather than the hyper-stressed level typical of those for whom being busy, or appearing to be busy, is considered the ultimate goal.

The volume knob is turned down to a manageable 8 even in the heart of the city. New York runs at a constant 11 and it is impossible to walk down any street without hearing the details of everyone else’s conversations, whether they are speaking to each other in person or on the phone.

Although having said that, the L train is insanely noisy for anyone who is not on it, and for those who are it still makes quite a racket. But it’s not the continuous, relentless din that aurally assaults you in the Big Apple which leaves you exhausted.

The food scene is amazing and has something for everyone

I can’t believe I’ve got this far without mentioning food. This is one of the best cities in America in which to be hungry: provided of course that you have money. It’s great value too – even the most sumptuous of meals will cost less than it would 800 miles further east.

But it’s at the lower end of the price scale that I believe the most interesting discoveries can be made.

Tur doggin

I still tell people about the gourmet hot dogs at Frank ‘n’ Dawgs to this day, two full years after first tasting one. And my mouth still waters at the thought of chowing down on a Tur-Doggin (turkey & date sausage, crispy duck confit, herb garlic aioli, pickled onion relish & pickled carrots) with triple truffle fries and a root beer.

Chicago has been at the forefront of the ‘pimp classic fast food’ movement for years and the humble hot dog, burger and pizza have been transformed in ways you never thought possible. Yet the originals are all here too; deep dish pizza and a traditional hot dog are as Chicago as it comes. Regarding old-school hot dogs, do NOT ask for ketchup, in fact don’t change your order in any way – it ain’t broke and it don’t need fixing.)

Food is taken seriously but there’s little snobbery even in classy joints. In other words, it’s dining as it should be – for the food and for the company. You know what? You don’t need to photograph everything either…

There is more craft beer here than you can drink in a week

Goose Island

Even more amazingly, it took me this long to mention beer. Chicago is craft beer nirvana, home to Goose Island which is one of the most successful microbreweries the world has seen. It also has the best story – started 25 years ago by a disillusioned cubicle worker with a love of a good pint. He quits his job, starts a microbrewery and bingo – the American Dream comes true.

You’ll find Goose Island beer all over the city and it is exported globally (I can even buy it in little old Trondheim, Norway). The mighty Anheuser-Busch snapped up the company a few years back for a pretty penny but it is still functioning as it once was – producing superb beer without a trace of the industrialisation that beer-lovers feared when the big boys came knocking.


But there’s so much more than just Goose Island – it seems like a new microbrewery opens every week in Chicago and standards are exceptionally high – Haymarket is one of my favourites as I like my Belgian beer and they have good food too.

Not a beer person? Craft spirits, then?

It was inevitable that the craze for all things ‘craft’ and ‘artisanal’ would spread, and it has. KOVAL Distillery recently won a best international whiskey award, the Chicago Distilling Company uses local grains and CH Distillery rules the vodka roost.

You can hear the blues every night of the year


Don’t tell me you still need convincing? First, you should check your pulse and then read that heading again. Every night is blues night in Chicago, and everyone loves the blues, right?

Buddy Guy has his own club, Legends, which is perhaps the best-known and the one most visitors head to. I’m sure it’s amazing but I managed to time my only free night in Chicago with Labor Day, when Legends was closed. So we headed to one of the myriad of smaller alternative venues, Blue Chicago. And subsequently had one of the best nights ever – quality music, cold beer, cheap entry and a fun crowd.

Seriously, you need to do this too – after a day seeing the sights, an evening enjoying the blues is hard to beat.

Riding the L train makes public transport fun. Really.

L train

The elevated train (‘El’ or ‘L’) is the coolest way to get around, no question about it. You’ve seen it in films, you’ve driven under it in video games but you have to ride the thing for real.

It’s incredibly loud (at least from the outside) and in need of some TLC, but who cares? It has character and charm, it’s cheap and it actually goes places you want to go too. But getting somewhere is not the point; it’s the ride that counts. And the hilarious station announcements – where do they find these voice recording artists?

Riding a Divvy bike is even better

Divvy bike

During the warmer months you can take advantage of the city bike rental scheme, somewhat comically called Divvy. Granted it’s only somewhat comical for English visitors with a childish sense of humour, to everyone else it makes perfect sense. And it’s an excellent scheme; with a credit card you can rent a bike from one of the many stands all over the City and explore at will for a reasonable cost.

I’ll be writing more about this in a future article but just take it from me that biking around Chicago is immense fun and gives you freedom to explore at will. Ask my buddy Frank in the picture there – we cycled miles around town and loved it. Just don’t ride on the pavement (‘sidewalk’).

And it’s not a good idea to ride down into the underground road system (yes, the one where Batman confronts the Joker in the Dark Knight). I did, and survived, but it was a little hair-raising, quite possibly illegal and once you’re in there, you can’t get out for a few miles…

Underground tunnels chicago

I went down there on a bike. I wouldn’t suggest you do the same.

But best of all, take to the water

Again it’s a summer only activity, but a cruise on the Chicago River is a must.

CAF boat

Make sure you sign up for the ones run by volunteers from the Chicago Architecture Foundation as you’ll learn all about this amazing city, its history and of course its architecture in a fun and interesting presentation while you cruise.

Wrigley building at night from boat

The evening cruises are even better if the weather is good. The ship’s bar does a mean Bloody Mary, too. Just saying…

They have even managed to solve winter


Well almost. The Pedway is an amazing system of (not always) interlinked tunnels, underground shopping areas and walkways designed to provide relief from the bitter Chicago winter in the Loop area. It’s a well-kept secret although a bit of Googling will help you on your way and I put some more details in an earlier article. The entrances are signposted but the real fun is the feeling of taking part in a subterranean treasure hunt, where the treasure is actually finding the system itself.

You want sights you say? I’ll give you sights…

Traditionalist, eh? OK. First let me give you a major tip: buy yourself a City Pass. I did on my first visit and it saved me a lot of time and money – City Pass were kind enough to let me have one for free on my return so thanks to the company for making this article even easier to write.

Prices and information valid March 1, 2014 – Feb. 28, 2015

With Chicago CityPASS ticket booklets, visitors skip most main-entrance ticket lines and save half off regular combined admission prices. Cost: $94 adults (value $187); $79 kids, 3-11. Purchase online at CityPASS.com or at any of the participating attractions. Includes:

  • Shedd Aquarium
  • Skydeck Chicago Fast Pass
  • The Field Museum
  • Museum of Science and Industry, Chicago, OR 360 CHICAGO Fast Pass (formerly the John Hancock Observatory)
  • Adler Planetarium OR Art Institute of Chicago

I was happy to use my own cash in 2012 and would absolutely recommend the system for anyone wanting to visit more than two or three of the major sights in the city. Speaking of which…

So you want to do some sight-seeing, try these for size:

Chicago has the Sears Tower

View from Sears to Hancock

Look it’ll always be the Sears Tower to me, okay? It’s going to take a generation or two before you get blank looks if you ask a local for directions using the old name – if that ever actually happens. But yes, it is now called the Willis Tower. It doesn’t matter that it’s no longer the highest building in the world (a title it held until 1998) or even the USA. Okay New York, you can have that one.

It may not be the prettiest skyscraper, but it is undeniably cool. Resplendent in black aluminium and glass, it’s little wonder Batman chose to survey ‘Gotham’ from its outside in “The Dark Knight”. It’s a 108-storey engineering marvel with a simple, building block design – the LEGO Architecture version must be one of the easiest in their range. But even if you’re not as taken by the exterior as I am, you’re going to love the views from the top.

Unless you have vertigo, in which case you’ll probably have been put off reading this part by the photo there.

Sears down

On a clear day you’ll see 100 km over four states from the Skydeck, and straight down 400 metres to Wacker Drive from the glass boxes that stick out on one side. Who in their right mind wouldn’t want to find out what that feels like?

If that wasn’t enough, it has the John Hancock Center too

Hancock building

‘Big John’ is a hundred metres shorter than his bigger rival, but is big nonetheless. The Hancock Centre is arguably better-looking and undeniably has a better location affording views over the lake and of the fabulous Loop skyline. There are several other reasons why you should come here too; the observatory level (94th floor) has a section open on one side to the noise and wind apart from a heavy-duty mesh screen and a ton of information about the building and its surroundings.

The new attraction here is ‘Tilt’ which is a vain attempt to compete with the glass boxes of the Skydeck. Basically you start off standing vertically then hold on tight to the handles as a section of the glass wall swings out; all good fun. The Hancock also has an excellent bar two storeys higher up where the view comes free with the stiff drink you may need to enjoy it. Prices are stiff too, as you’d expect, but if you don’t go nuts it’ll be cheaper to get the vista this way. You should do both though…  

Yes, there are museums and all that stuff

Culture vulture? Chicago has enough to keep you occupied. Start with these three Windy City institutions all within a baseball throw of each other:

Field Museum of Natural History

Sue at the Field

You can’t come to Chicago without paying a visit to Sue. The biggest T-Rex yet discovered, she rules over the ground floor in the same way the strangely nameless Diplodocus does at the Natural History Museum in London. But the huge yet manageable and rarely over-crowded Field Museum has more to offer than dinosaurs.

Don’t miss the African section which I guarantee will make you long to return to this amazing continent if you’ve been there before and consider a trip if you haven’t. Don’t miss the totem pole collection, the hall of gems or the mummies (natch) either.

Shedd Aquarium

Inside this striking circular building from 1920 you’ll find an enormous ‘oceanarium’ holding 4 million gallons of water and a lot of fish. I know 4 million gallons is a little hard to visualise but it’s big, put it that way.

For most visitors the sharks are the main attraction – or rather the opportunity to experience them swimming around and above from the safety of the observation area. Say hi to Granddad, an esteemed lungfish who has been here for 81 years and is the oldest aquatic mammal in captivity. He was brought here for the World’s Fair in 1933 and has become the Shedd’s most famous resident.

There’s a 4D cinema here too if the live action isn’t quite enough.

Adler Planetarium


It’s worth coming out here even if you don’t go inside the Adler, but of course you should. One of the best views of the downtown skyline can be had from right outside the planetarium, and the building itself is a 12-sided thing of beauty.

Learn about space, view the excellent exhibits and don’t miss one of the high-tech projection/live action shows which are both informative and very American at the same time – bordering on the naff but definitely worth catching.

Not enough for you? I’ve got more you know

It doesn’t stop there – but I have to stop at some point so I will try to be brief:

The Art Institute of Chicago

It’s the second-largest art museum in the country (that ‘s’-word again…) and the building is as impressive as the collection it houses.  The major attractions here are American Gothic and Nighthawks  but it also contains the largest number of impressionist and post-impressionist paintings outside of France. So there.

Museum of Science and Industry

I’ve written about this already but suffice to say that it’s one of the best science museums on the planet. You can set off a tornado, check out the Apollo 11 lunar module and it tops all the above with a German U-boat complete with Hollywood audiovisuals. Just go.

Crave something a little more left field? We can do that too

International Museum of Surgical Science

There are more details in a previous article, but no – it’s not for the squemish.

Leather Archives & Museum

Yes, really. If you ever fancied spending a few hours getting better acquainted with your dark side, this museum of leather, festish and S&M should, er, hit the spot.

Smith Museum of Stained Glass Windows

Possibly even more niche that the previous listing, this place is more interesting that you’d perhaps expect with 150 exhibits including one Michael Jordan. In stained glass.

Like your movies? Go location spotting then!

I might have mentioned Batman once or twice. Why not go have a look at the place they flipped the truck in the Dark Knight? Wayne Towers is not far from there but Chicago was popular with film-makers long before Nolan came.

Union station

Remember The Untouchables? That scene with the pram bumping down the stairs? Union Station.

Ferris Bueller’s Day Off? Lake Shore Drive and many more. Keep your eyes open, and you’ll recognise plenty of places from the silver screen.

Even the most hardcore sports hater will have a good time at Wrigley Field


I’m not a sports guy, but I loved watching my first baseball game at Wrigley Field. The stadium is 100 years old this year and its home team, the Chicago Cubs, hasn’t won the series in almost as long.

There’s a reason for this, if you believe the story: Billy Sianis, the owner of the iconic Billy Goat Tavern (which you should also visit) was refused entry to the stadium because he took his pet goat with him.

Billy Goat Tavern

Sianis called down a curse on the Chicago Cubs saying that they would never win another World Series. They still haven’t, and that was in 1945…

But it doesn’t matter – the atmosphere is fantastic and uber-friendly, you can buy craft beer from your seat (salesmen parade constantly) and you can’t help but make new friends – especially if you don’t have a clue about the rules. They are surprisingly patient with newbies and love explaining in between pitches.

Oh and when we were there, the Cubs won.

The whole area around the stadium is a party zone on match day and the souvenir shops do a roaring trade in merchandise.

Fresh-air fan? Read on then


Open, green spaces have always been important in the design of the city and Millennium Park is perhaps Chicago’s crowning glory.

The bean from side

With regular free concerts in the Frank Gehry-designed Jay Pritzker Pavilion, the unfeasibly shiny and smooth Cloud Gate (better known as The Bean) and the nearby Crown Fountain there’s plenty to draw you here, just over the road from the Loop.

Crown fountain

Yup, it’s more fun in the summer here too.

Then go take a look at the stunning Buckingham Fountain which marks the start of Route 66. Every hour from 0900 – 2300 during the summer it does this:

Buckingham Fountain

And if you think that spray looks high, it is. 15 storeys in fact.

Navy Pier

Navy Pier

It’s a bit of a tourist trap and many locals avoid it, but Navy Pier is the top attraction in the city. It’s best for families although the Ferris wheel is pretty amazing for everyone and adults will appreciate the beer garden here in the summer. The fireworks display on Wednesday and Saturday nights in the high season is fun too.

Chicago has proper beaches. With sand.


See? There are plenty of beaches on the Lake Michigan shore to enjoy during the warmer months with Oak Street being the place to laze in the sun and North Avenue the one for more active folk to see and be seen. And play volleyball. There are beach bars and bistros too, meaning you can spend the whole day here without much trouble.

Shopaholics will not be disappointed

The Magnificent Mile lives up to its name and just about every US store can be found here. If shopping is your thing your appetite should be sated on this stretch of Michigan Avenue. If you are after something more unusual head try Lake View or Wicker Park. You might have guessed that shopping is not my top priority and there’s no coincidence that the subject appears at the bottom of this list, but I am reliably informed that it’s good here.

Phew. I could go on, but instead I’ll leave it here and can promise you a bunch more Chicago articles to whet your appetite for the greatest city in the USA.


Now let me hear if you’re convinced – or have I got this all wrong? Get commenting then!

Andy Higgs
Andy Higgs

I know what it's like to go from being a crazy backpacker without a care in the world, via being a vaguely sensible parent to being an adventurer once more. In other words, evolving into a Grown-up Traveller.

Like everyone else, I love to travel, have visited a lot of countries and all that but my big thing is Africa.

I also own and run The Grown-up Travel Company as a travel designer creating personalised African itineraries for experienced adventurers

Articles: 1279


  1. The Magnificent Mile is Michigan Avenue, not North Avenue.
    The rest is spot-on, though. Yes, my city is the Best City in the World. 🙂 Thanks!

    • You got me 🙂 Actually (and I realise this won’t sound believable, but it is true!) I spotted this just after I published because I was editing photos including one of the double street signs. For some reason I got distracted and forgot about it – I have no idea where I got North Avenue from either! I’ll make the change and thanks for pointing it out. Yes, your city is definitely one of the best in the world – I need to travel a bit more for a definitive top ten though!

  2. I have lived here. over 25 years and I think it’s the greatest.Cleanest city!!!
    Thank for taking the time to see my great city and. write a very consise article. May I recommend neighborhood s next. and start with Hyde Park Museum. of Science University of Chicago. President Obama’s. home this area is the beginning. of this great city.

  3. I spent two weeks Chicago one summer when I was a teenager. I loved the museums – especially the Museum of Science and Technology. We spent weekends sailing on Lake Michigan, which they told we was lined with chicken bones and beer bottles. The architecture was amazing..

    • The museums are a really big draw yet Chicago has so many – and Lake Michigan is beautiful. I could not believe the colour of the water on my first visit and you really feel like you’re on the ocean because it’s so huge. I’ve been to quite a few big cities but none have the same appeal as Chicago – I’d rather live there than my home town of London if I ever moved from Norway – and that’s saying something as I’m a big fan of London… 🙂

  4. Thanks for sharing. I hope you continue to have such quality blog to share with everyone! I believe there will be many people who share my views when they read this blog from you. Those who come to read your blog will find lots of helpful and informative tips

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