Could Chicago be the best city in the States? Our Essential Guide to the Windy City

It’s easy to panic when you get to a place like Chicago. There’s so much to do here you don’t know where to start and the sharp claws of FOMO can really dig into your side. Our first-timer’s guide to Chicago is here to help.

Chicago essential guide

Chicago is full of fascinating history, beautiful architecture, incredible food and wonderful people. 

We’ve been lucky enough to visit this – my personal favourite American city – a couple of times now. It’s one of those excellent places that gets better every time you visit.

Simply walking the streets of the city will give you plenty to do, but our essential guide to Chicago will hopefully give you a bit more direction. It’s not an exhaustive guide by any means, so please feel free to add your own suggestions and recommendations in the comments below.

Essential guide to Chicago, IL

One more caveat before we get stuck in: although we’ve included a few local tips, this is a list based on our own experiences – we’re just a couple of people visiting from overseas.

Where to stay in Chicago

Being a big city, there are literally hundreds of places to stay in Chicago – and that’s before you even look at things like AirBnB.

But here are three hotels right in the Magnificent Mile and the Loop that we’ve enjoyed:

Kimpton Monaco Chicago

225 N Wabash Ave, Chicago

Perfectly positioned on the south bank of the Chicago River, the Kimpton Monaco is not only in the best location it also provides incredible service. Kimpton hotels are well-known for their above-and-beyond attitude, and the Monaco is no exception.

Our suite looked out over the river and was a highlight of one of our most memorable trips to the States.

Here’s our review of the Kimpton Monaco and video walkthrough.

Where to stay in Chicago - Kimpton Hotel Monaco Chicago - suite view

Kimpton Gray

122 W Monroe St, Chicago

Deep in the business district of Chicago, you might not think the Kimpton Gray is in the best spot for holidaymakers. However, this city isn’t like most others, where the CBD falls dead on its face outside office hours. It’s alive all the time.

You’re also close to some of the best sights in the city.

For hotels, you can’t get much better than this newly renovated piece of Chicago history. In fact, this was the tallest building the world for a little while.

Check out our full review and video walkthrough of the Kimpton Gray here.

Where to stay in Chicago - Kimpton Gray Hotel Review Chicago

W Chicago Lakeshore Hotel

644 N Lake Shore Dr, Chicago

If your priority is to stay as close as possible to Lake Michigan, this hotel is for you. From the windows of our large ‘Spectacular King Room’, we had superlative views out across the water and the turning lights of the Ferris Wheel and Navy Pier.

From here, you’re a stone’s throw from Ohio Street Beach, Navy Pier and of course the Magnificent Mile.

Click here for our our review of the W Lakeshore.

Things to do in Chicago

There’s just so much to do in Chicago it’s hard to know where to begin. But we’re surprised every time we talk to locals that they recommend one thing above all others to do if it’s your first time here:

Chicago Architectural River Cruise

We weren’t sure if this was going to be any good, but from beginning to end, it’s worth your time and money. You learn so much about this amazing city and you get to see Chicago from a completely different angle. Highly recommended.

You can buy tickets to the cruise here.

And here’s our review of the Chicago Architectural River Cruise for more info – and an embarrassingly old photo of me!

Cloud Gate

Synonymous with Chicago is the giant silver sculpture near Millennium Park. Better known as ‘The Bean’ to the initial chagrin of its creator Sir Anish Kapoor, Cloud Gate is an iconic piece of public art that you just have to go look at. Its distorting reflections of the city skyline make for a fun photo, and walking underneath its 3.7m archway is a real trip.

The Bean/Cloud Gate, Chicago, IL

Chicago Cultural Center

78 E Washington St, Chicago

Within the walls of the beautiful late-1800s building, which was once home to Chicago’s first public library, the Cultural Center is one of the city’s most visited places. Its magnificent stained glass domes and unusual decorations are fascinating, and the range of public exhibitions here means there’s always something to see.

Chicago Cultural Center, Chicago, IL

Buy a Chicago CityPASS booklet

If you’re here for a few days, the Chicago CityPASS booklet gives you some awesome discounts (around 50%) on entrance tickets to the best sights of Chicago. The booklet also gives you great tips on the best time to visit each attraction, a top tip for your visit and also where to find food nearby.

You can buy the booklet online and have a digital copy on your phone, have a hardcopy booklet delivered to your hotel or pick one up at the listed venues. Either way, it’s the same price.

You’re given access to some of the best, most popular sights, and many of them give you express-lane access with this booklet too.

Here’s what’s in the Chicago CityPASS booklet:*

Skydeck Willis Tower

For a long time, this was the tallest building in the world. It’s till pretty high though! The glass boxes sticking out of the side of the building are an amazing experience. The express pass you get with the CityPASS book is worth its weight here.

Skydeck Willis Tower and us, Chicago, IL

Shedd Aquarium and Field Museum

We haven’t managed to get to these two places yet, but they look great. The Field Museum has an impressive collection of artefacts from Ancient Egypt and the largest, most intact fossil of a T Rex.

Either the Adler Planetarium OR Art Institute of Chicago

We didn’t go to the Adler Planetarium, but the Art Institute is awesome. More of an art museum, this place has an incredible range of works, including a huge Monet collection, which is wonderful to see. But there’s art here dating back 3,200 years. You could spend all day here, it’s a massive complex.

Georges Seurat, Art Institute of Chicago, Chicago, IL

360 Observation Deck Hancock Tower OR Museum of Science and Industry Chicago

The Hancock Tower – also once the world’s tallest building – gives you completely different views of the city, four other states and of course the sparkling waters of the lake.

A neat trick to get up to the top of the tower without paying or queuing for the observation deck is to go to the bar the level below. Grab a seat by the window and enjoy one of the best martinis you’ll ever have.

Chicago essential guide - Hancock Tower martini

The Museum of Science and Industry is in fact the last remaining building of the 1893 World’s Fair that really put Chicago on the map. Not only is this a stunning building, but it’s also the biggest science museum in the country.

*These attractions were correct at time of writing. Attractions in the booklet may be added and removed over time.

Visit the villages

A quick train ride north and west of the city centre will put you amongst a much more authentic Chicago than the one you see in the Loop or Mag Mile. Here are few we’ve been to and loved.

Bucktown and Wicker Park

Exploring the streets around these two suburbs with show you the more affluent semi-urban neighbourhoods of Chicago. Plenty of bars, restaurants and cafes here make it tempting to spend a lot more time around here.

Logan Square

With a bit more grit than Bucktown and Wicker Park, Logan Square has only recently been gentrified. There are still plenty of signs of this suburb’s tough past. There are some amazing bars, breweries and distilleries around here that are essential.

Revolution Brewing, Chicago Distilling Co, Scofflaw and Best Intentions are all awesome for drinks, chats and food.

Where to eat in Chicago

Chicago is an eating paradise. The food options here are amazing. From deep-dish classics to unique foodie spots hidden well away, here are a few we’ve fallen in love with.

Bar Biscay

1450 W Chicago Ave, Noble Square, Chicago

Perhaps one of the most understated, yet wonderful dining experiences you’ll have, Bar Biscay focuses on food specifically from the Atlantic side of Spain and a bit if France. The food is simple, but the dishes are well-executed – a tough balance to achieve. The bar here is also spectacular.

Bar Biscay, Chicago, IL

Rootstock Wine & Beer Bar

954 N California Ave, West Town, Chicago

Apart from one of the owners – Johnny Hap, we’re talking about you – being a bit of a nob, this place is cool. Their wine list is interesting and there’s a comfortable lived-in feel to the restaurant. As for the food, this may well be the best burger I’ve had. Big call, but it was superb.

Burger at Rootstock, Chicago, IL

Billy Goat Tavern

430 N. Michigan Ave at Lower Level, Chicago

A bit of an institution and a strange ol’ place to visit, this burger joint even has a Saturday Night Live sketch based on it. There are a few Billy Goat Taverns around the city these days, but the original is on the lower level of N Michigan Avenue. The burgers are bloody tasty by the way.

Chicago essential guide - Billy Goat Tavern Cheezborga


100 W Ontario St, Chicago

The Chicago hotdog is a unique creature. And it’s what Portillo’s has made its own. Generally, a Chicago hotdog has a lot of pickle on it and sauerkraut. Portillo’s does it best.

Portilllo's hotdogs, Chicago, IL

Oak Street Beach Restaurant

Talking of Chicago hotdogs, my first experience with one was at the Oak Street Beach Restaurant. Not only do you get to chow down on a fine example of a Chitown dog, you get to enjoy the people-watching on this popular lakeside beach.

Chicago essential guide - Clark St Beech hotdog

Deep dish pizzas

Most locals won’t give you much for deep dish pizza recommendations. It’s not somewhere they usually go. However, if you push them, they’ll usually say either Giordano’s or Lou Malnati’s.

Giordano’s is pretty good, but it’s actually a ‘stuffed’ pizza with the cheese between two bases and rich tomato on top.

Chicago essential guide - Giordano's Pizza

Malnati’s is the real deal with only one really deep dish. It’s something you should definitely experience once… maybe twice!

Lou Malnuti's Deepdish Pizza, Chicago, IL

Recommendations from a local

With the limited time we’ve had in Chicago, we think we’ve done ok, but there’s still this list our Uber driver from the airport gave us (we love an Uber recommendation!) that we’re working on:

Al’s Beef – for another Chicago classic: the Italian sandwich.
I’ve heard that Carm’s in Little Italy is also amazing for its sandwiches.
Gibson’s Restaurant Bar – a city-central steakhouse
Heaven on 7 – great Cajun food
Ocean Prime and Harry Carey’s – both steakhouses with great reputations

Where to drink in Chicago

We were very excited to learn what excellent drinkers Chicagoans are. They love a sherbet. Because of that, there’s a whole host of watering holes all over the city. Supply and demand, baby!

Clark Street Ale House

742 N Clark St, Chicago

Possibly my favourite beer bar ever, I discovered Clark Street Ale House at the very start of a solo self-guided bar hop (sounds sad but I actually had the best time) back in 2013. They have an amazing selection on tap here that’s constantly changing. Snag a seat at the bar and enjoy the banter.

Chicago essential guide - Clark Street Ale House

Revolution Brewing

2323 N Milwaukee Ave, Logan Square, Chicago

What a friendly place this is. From the moment we walked in to the point we dragged ourselves away, we loved it here. Truly superb beers made and poured here. The food is great too.

Revolution Brewing Co, Logan Square, Chicago, IL

Chicago Distilling Co

2359 N Milwaukee Ave, Logan Square, Chicago

Just down the road from the Revolution Brewery, this distillery and cellar door has a very cool vibe but also some of the best rye and single malt whisky you’ll find. We took a bottle of their Blind Tiger Rye away with us. They also do great cocktails here. My corpse reviver hit the spot!

Chicago Distillery, Chicago, IL

Bar Biscay

1450 W Chicago Ave, Noble Square, Chicago

The food is great here and that’s Biscay’s focus. But the bar deserves its own mention. Not only are the shelves insanely well-stocked but the people holding the shakers really know what they’re doing.

Best Intentions

3281 W Armitage Ave, Logan Square, Chicago

That sweet spot between a dive bar and a speakeasy, Best Intentions is a lot of fun. From the ‘Fancy Cocktails’ sign above the bar to the old-school arcade games out back, you’ll want to stay here for just one more after each round.

FYI, they serve Angostura bitters on tap here. Try it – they serve it in a shot and it’s actually awesome.

Scofflaw speakeasy, Chicago, IL


3201 W Armitage Ave, Logan Square, Chicago

This swanky little bar does a very fine (enormous) martini – to the point where we needed to put the glass on the table and trust the meniscus!

Well worth your time, Scofflaw (a name for an illegal drinker during Prohibition) is the embodiment of hygge – that Norwegian word for a cosy place that makes you feel comfortable and at ease.

Redhead Piano Bar

16 W Ontario St, Chicago

Have you ever had the feeling that you’re actually on a film or TV set and not real life? That’s kind of what you get at Redhead’s.

When you grab your drink and go and stand at the round bar, and listen to the pianist playing Piano Man in the middle of it while everyone – and I mean everyone – sings along… it’s magical and so much fun.

There’s also a great little courtyard here perfect for a late-night cigar… they even have a humidor. Just sayin’.

Redhead Piano Bar

How to get to Chicago

It used to be a long and annoying journey with at least one connecting flight to get to the Windy City from Australia. But that’s all changed now.

As of April 2020, Qantas has direct flights from Brisbane straight to Chicago, with plans to fly direct from other major Aussie cities, including Sydney, coming together nicely.

Otherwise, why not just get anywhere Stateside and work your way to the Windy City through one of the greatest countries to travel in. Our last trip to Chicago, we arrived via Kansas City, MO – barbecue of the world!

You can read more about our time in KCMO here.

Chicago essential guide

Do you have any hot tips for exploring Chicago? Tell us in the comments below!


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