Right, let’s get one thing straight from the beginning: Chicago ain’t that windy. It’s not the windiest city in the USA, it isn’t even particularity windy on any known scale of windiness. Sorry.
What it IS however, is a vastly underrated metropolis chock full of attractions, sights and, most importantly, pizza. So much pizza.
I loved visiting Chicago, I only planning on spend a weekend here, but liked it so much I stayed for a week. During summer there is so much going on from free concerts, beaches, live sport, amazing bars and so much more.
View my insider tips for visiting Chicago including the essential things to do.
Getting to Chicago
From outside the US, or from other main cities you can find direct flights to Chicago on Skyscanner. From other destinations in the US you can also get around by train, bus or drive which is a lot cheaper than flying. Distances overland to Chicago from other popular tourism destinations like Boston and New York are long though, so be aware of this.
Where to Stay
I would recommend staying in the city centre, this way most tourism attractions are walkable.
I stayed at Hi Hostel Chicago, and absolutely loved it. Staying here was one of the main reasons I extended my stay, I was lucky to meet other travellers, and the hostel offered so much entertainment from nights out to free sightseeing tours.
For more options the best deals on hotels on Booking.com.
Getting Around
Considering Chicago is the third largest city in the USA it is pretty easy to get around whether you’re using trains, planes or automobiles. Going downtown from O’Hare Airport by cab costs around $35, from Midway about $25. Cabs in the city are not generally too hard to find, day or night. Parking downtown is between $10 and $20 a day. A single trip on the ‘El’ CTA trains or the bus is $1.50.
Chicago City Tours
If you would like to see new places and learn more about the city you can find sightseeing tours on GetYourGuide or Viator.
Top Things to See and Do in Chicago
You will never be short of something to do in the USA’s third-largest city. Chicago has some of the best theaters, galleries and restaurants as well as miles of beaches and dunes along Lake Michigan.
Read on for tips to make the most of your trip.
Go Deep
Love it or loathe it (and if you loathe it, who are you? Seriously? It’s like cake covered in cheese and sauce!), deep dish pizza is where it’s at in Chicago.
There’s much debate over where the best pizza in the city can be found, though it’s generally agreed that the original was invented at Pizzeria Uno (now Uno Chicago Grill).
With dozens of lists of “best” pizza restaurants, fiercely fought online battles amongst various loyalists, and more choice that you can shake a gorgeous piece of golden crust at, there’s no real option here. You’ll have to try them all.
River Cruise
Catch the 90-minute cruise run by the Chicago Architectural Foundation. Not only will you learn about the history and construction of some of America’s greatest buildings from a trained volunteer, but you’ll appreciate the breeze on one of those hot summer days.
Millennium Park
No list of Chicago highlights would be complete without the inclusion of this popular park and, crucially, its “Cloud Gate” sculpture, more commonly known as “The Bean”. You’ll recognise it from almost any film set in Chicago, any picture of Chicago and even the odd video game.
Hit The Beach
The beach? In Chicago? Yep! Situated as it is on the shore of Lake Michigan, Chicago has over 26 miles of public beaches. Illinois Beach State Park is great for camping and hiking, Kathy Osterman Beach is famous for it’s clear water and North Ave. Beach is the place to be seen as the most popular stretch of sand in the city.
Willis Tower
Probably the first thing you will see in Chicago in the skyline. For mile upon mile across the flat prairies you watch the towering edifices of the Windy City drawing ever closer. Chicago’s buildings are not just big, they are also some of America’s greatest architectural achievements.
It was here that the first skyscraper was built back in 1885. The city still has three of the world’s ten tallest buildings; the Willis Tower, the Hancock Center and the Amoco building.
The Willis Tower, formerly known as Sears Tower, is the second highest skyscraper in the USA behind the One World Trade Center in New York. It’s iconic on the Chicago skyline and can be seen from everywhere, and it is an essential stop on any Chicago itinerary.
Go up for breathtaking views, there is also a scary high glass bottom floor for anyone brave enough.
Live Sports
Chicago is home to some of the most famous teams in North America including the Chicago Bulls, Chicago Cubs, and the White Sox. Watching a live game can be an amazing experience, the atmosphere on match days incredible.
Take me out to a ball game at Wrigley Field. Step back in time to see the Cubs against the backdrop of ivy-colored walls and a hand-cranked scoreboard. Wrigley Field home to the Cubs baseball team is one of the best stadiums in the US.
Culture
Bring your comfortable shoes to explore one of the world’s great galleries, the Institute of Art. The Chicago Art Institute is home to the world’s largest collection of impressionist paintings outside Paris along with a stunning collection of classic American works.
It may be best-known for its stunning collection of impressionists and American art, but don’t miss the modern photography or African sculpture. Admission is free every Tuesday. The quality of theatre and classical music in Chicago should kill the mistaken belief the Midwest is without culture.
Live Music and Nightlife
For those who like their music a little more casual, there is plenty here. The legacy of the urban blues, which was born in the city’s South Side, lives on in the huge variety of bars and clubs.
Get down to Buddy Guy’s Blues Legends. The urban blues was born in Chicago and this place, owned by the wailing guitar great himself, is the place to see it. And the down-home Southern cooking’s great too.
The rock scene continues to thrive, as can be seen from the bands it has produced in recent years including the Smashing Pumpkins and Wilco.
Prices for a night out are pretty good too. The quality of food reflects the ethnic diversity of the city and is every bit as good as New York or LA. But people used to eating in those cities will get a pleasant surprise when the check arrives.
Beer Tasting Tour
Need a drink to go with your pizza? Chicago takes beer almost as seriously as the deep dish and many of the local breweries run tours where you can sample the product as you see how it’s made. If you’d like to take in more than one type of tipple, a walking tour of the city’s bars and pubs might be more your style.
Get Festive
Lollapalooza, Blues Fest, Taste of Chicago, Chicago Jazz Festival, Windy City LakeShake…the list goes on! Chicago has over 200 festivals, events and celebrations this year alone so you’re bound to catch at least one. Lollapalooza in particular is a brilliant event with line-ups to rival Download or Glastonbury, and a massive variety of music to suit almost any taste.
Chicago Restaurants: Places to Eat
With over 100 nationalities represented in the city, there will always be a cuisine that you have never tried before. But don’t miss out the hometown classics.
A Chicago-style hotdog is a delicacy not to be missed. It should be a pure beef frankfurter on a steamed bun with mustard, relish, onions, tomatoes, peppers, pickle and a dab of celery salt. Plenty of good places serve them, but you’ll find it hard to beat the Vienna Beef Factory Store & Deli.
Chicago’s other culinary claim to fame is the deep-dish pizza. Two restaurants claim to have invented it, Gino’s and Pizzeria Uno. For us the Original Gino’s East of Chicago wins on both food quality and atmosphere.
Further up the scale, in every sense, is the Signature Room on the 95th floor of the John Hancock Center. The food may be good rather than great, but that view makes up for everything.
The city is also home to one of America’s and the world’s great restaurants, Charlie Trotter’s. However it is described, ‘new American,’ ‘eclectic’ or ‘fusion’ cuisine, Trotter is the master. This is probably not the place for a romantic evening. Nothing should distract you from the food.
For those people whose idea of heaven is a well-prepared steak, Morton’s is the place to go. The formula of quality food and attentive service has spawned a chain, but this is the brown-wood original down on the Gold Coast.
Safety
Chicago has got quite a reputation for crime and gun violence, but as a tourist you will probably only stay centrally and so you will very unlikely encounter any issues. Most hotels and tourist attractions are in the city centre and walkable.
Plan a Trip to Chicago
Finally, though, it is the people that count. This is a mostly friendly place and pleasantly lacking in big city attitude. Come and see that culture and the Midwest are not opposites.