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 is full of fascinating history, stunning architecture, extraordinary food and terrific people.
We’ve been lucky enough to check out this – my personal much-loved American city – a couple of times now. It’s one of those exceptional places that gets better whenever you visit.
Simply walking the streets of the city will give you plenty to do, but our vital guide to Chicago will hopefully give you a bit a lot more direction. It’s not an exhaustive guide by any means, so please feel complimentary to add your own ideas and recommendations in the comments below.
Essential guide to Chicago, IL
One a lot 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 checking out 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 ideal in the stunning 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 supplies extraordinary 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 a lot of memorable trips to the States.
Here’s our review of the Kimpton Monaco and video walkthrough.
Kimpton Gray
122 W Monroe St, Chicago
Deep in the service district of Chicago, you might not think the Kimpton gray is in the best spot for holidaymakers. However, this city isn’t like a lot of 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.
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 stunning 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 shocked whenever we speak 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 remarkable city and you get to see Chicago from a completely different angle. highly recommended.
You can get tickets to the cruise here.
And here’s our review of the Chicago Architectural River cruise for a lot more info – and an embarrassingly old photo of me!
Cloud Gate
Synonymous with Chicago is the gigantic silver sculpture near Millennium Park. better known as ‘The Bean’ to the initial chagrin of its designer Sir Anish Kapoor, Cloud gate is an famous 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.
Chicago cultural Center
78 E Washington St, Chicago
Within the walls of the stunning late-1800s building, which was once home to Chicago’s first public library, the cultural center is one of the city’s a lot of checked out places. Its stunning stained glass domes and unusual decorations are fascinating, and the range of public exhibitions here indicates there’s always something to see.
Buy a Chicago CityPASS booklet
If you’re here for a few days, the Chicago CityPASS booklet gives you some amazing discounts (around 50%) on entrance tickets to the best sights of Chicago. The booklet also gives you terrific ideas on the best time to check out each attraction, a top idea for your check out and also where to find food nearby.
You can get 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 provided venues. Either way, it’s the same price.
You’re given access to some of the best, a lot of popular sights, and lots of of them give you express-lane access with this booklet too.
Here’swhat’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 remarkable experience. The express pass you get with the CityPASS book is worth its weight here.
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 excellent collection of artefacts from ancient Egypt and the largest, a lot of 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. a lot more of an art museum, this place has an extraordinary range of works, including a substantial Monet collection, which is terrific to see. but there’s art here dating back 3,200 years. You could spend all day here, it’s a enormous complex.
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. get hold of a seat by the window and take pleasure in one of the best martinis you’ll ever have.
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 sensational building, but it’s also the greatest science museum in the country.
*These attractions were right 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 a lot 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 a lot more affluent semi-urban neighbourhoods of Chicago. plenty of bars, restaurants and cafes here make it tempting to spend a lot a lot more time around here.
Logan Square
With a bit a lot more grit than Bucktown and Wicker Park, Logan Square has only recently been gentrified. There are still plenty of signs of this suburb’s hard past. There are some remarkable bars, breweries and distilleries around here that are essential.
Revolution Brewing, Chicago Distilling Co, Scofflaw and best Intentions are all amazing 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 special 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 terrific 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 hard balance to achieve. The bar here is also spectacular.
Rootstock white 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 white 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.
Billy Goat Tavern
430 N. Michigan Ave at lower Level, Chicago
A bit of an institution and a odd 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.
Portillo’s
100 W Ontario St, Chicago
The Chicago hotdog is a special 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.
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 take pleasure in the people-watching on this popular lakeside beach.
Deep dish pizzas
Most locals won’t give you much for deep dish pizza recommendations. It’s not somewhere they normally go. However, if you push them, they’ll normally 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.
Malnati’s is the real deal with only one really deep dish. It’s something you must absolutely experience once… maybe twice!
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 motorist fromthe 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 remarkable for its sandwiches.
Gibson’s restaurant Bar – a city-central steakhouse
Heaven on 7 – terrific Cajun food
Ocean Prime and Harry Carey’s – both steakhouses with terrific reputations
Where to drink in Chicago
We were very ecstatic to learn what exceptional 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 much-loved 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 remarkable selection on tap here that’s regularly changing. snag a seat at the bar and take pleasure in the banter.
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. genuinely outstanding beers made and poured here. The food is terrific too.
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 amazing 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 terrific cocktails here. My corpse reviver hit the spot!
Bar Biscay
1450 W Chicago Ave, Noble Square, Chicago
The food is terrific here and that’s Biscay’s focus. but the bar should have 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 a lot 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
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 depend on 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 get hold of 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 indicate everyone – sings along… it’s magical and so much fun.
There’s also a terrific little courtyard here best for a late-night cigar… they even have a humidor. just sayin’.
How to get to Chicago
It used to be a long and bothersome 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 by means of Kansas City, MO – barbecue of the world!
You can read a lot more about our time in KCMO here.
Do you have any hot ideas for exploring Chicago? tell us in the comments below!
