Chicago Illinois, the Windy City, the Gateway to the Midwest is without a doubt one of our favourite places in North America to travel to. From the incredible food, to brazen cocktail culture, the stunning Gotham-esque architecture to modern art, the music, sports, friendly people and more, it’s hard not to fall instantly in love with Chicago. So whether you are a Chic-Town vet or a newbie, we have compiled a list of things to do while in the city. Read below and start planning your trip now!

Millennium Park

Cloud Gate & Millennium Park

This is a must, basically, you want to go here to get your official “I’m in Chicago selfie” at the “Bean”. The mirrored Cloud Gate statue is always busy, and we mean rammed. If you don’t mind swarming packs of people then go whenever, but the real trick is to get there early. Like 7:00 am on a saturday early. If you go then, all you have to compete with his a couple of eager beavers and a jogger or two. Photographic evidence in the banner above.

Located at 201 E Randolph St, Chicago, IL 60602, United States

Big Star Tacos Star

Big Star Taco

Probably the most popular taco joint in Chicago. Maybe not the best tacos, but between the crowd, the ambiance, the cheap beer and good vibes, this is the best place to spend an afternoon, evening or whatever eating tacos.

If you get there late on a weekend, expect to wait, but if you aren’t the waiting type, don’t worry they have a takeout window next door where you can get some tasty taco treats in about 20 minutes. No alcohol is served but they do have Mexican Coke in glass bottles. You know the Coco Cola that uses real sugar and tastes amazing? Yeah, that one.

Located at 1531 N Damen Ave, Chicago, IL 60622, United States


A Cub’s Game at Wrigley Field (In the Summer)

Got time to kill? Or want to spend the day in the sun? Head down to Wrigley Field to watch a Cubs game. The team isn’t the greatest, but they are legendary and Wrigley Field is actually a piece out of history. The stadium was built in 1914 and had been home to the Cubs since 1916. It’s outside, it’s historic, the beers are reasonable and the crowd is unbeatable. Even if the Cubs are getting smashed by the visiting team. Our hot tip is to walk up to the ticket window about 10 minutes after the game starts and score a pair of decent seats for real cheap. Like cheaper than a movie cheap.

Located at 1060 W Addison St, Chicago, IL 60613, United States

Cindys Rooftop Bar

Cindy’s Rooftop Bar

Enjoy a lovely and properly concocted cocktail (or coffee) while overlooking Millennium Park from the rooftop bar on the 12th floor. The view is simply breathtaking and gives you an incredible perspective of the Windy City. It is also photo-op heaven!

Located at 12 S Michigan Ave, Chicago, IL 60603, United States

Saint_Alfred Chicago

Saint Alfred

Located in the cool-guy Wicker Park area of Chicago, Saint Alfred is a sneakerhead oasis amongst trendy restaurants and bars. Specializing in providing the best streetwear and footwear from around the world, the little shop has one of the most impressive selections of specialty sneakers in the city. They also carry some hot apparel brands as well as their own in-house label which offers a uniquely Chicago point of view in the streetwear department. Definitely a must visit.

Located at 1531 N Milwaukee Ave, Chicago, IL 60622, United States

Perhaps one of the best places in Chicago to grab a cocktail for the cocktail. Located in the popular Logan Square, Longman & Eagle features innovative New American cooking with some incredible beverages. There is a no-reservations policy which means it can get real crowded and you will probably have to wait, but trust us, it is definitely worth it. If you can, we suggest sitting at the bar and making friends with the bartender (be sure to buy them a drink) and you will have an experience you will never forget.
Located at 2657 N Kedzie Ave, Chicago, IL 60647, United States
Duseks Brunch
Whether it’s brunch, lunch or dinner, one of our favourite spots in Chicago for food (but in particular brunch) is Dusek’s. From their always tantalising Instagram feed to their real life in person food, Dusek’s is worth the trip to Pilsen. Our advice on this one, give yourself a headstart by actually checking out the menu first. It can be overwhelming with excellence.

Located at 1227 W 18th St, Chicago, IL 60608, United States


Architecture Boat Tour

Architecture Boat Tour

No trip to Chicago would be complete without experiencing the Chicago Architecture Foundation River Cruise. Running up and down the Chicago River, these 90-minute tours are a wealth of history and knowledge. Many of them also serve drinks, which is nice. You’ll find out how Chicago grew from a small settlement into one of the world’s largest cities in less than 100 years. It is definitely worth the 90 minutes.

Located at 400 N Michigan Ave, Chicago, IL 60611, United States

Fido Roam Chicago

A Roaming Package

No matter where you go or what service provider you are with when you travel you need to have a date package. Aside from all the obvious Instagramming and Snapchatting you need to be doing, being able to find where you are on a Map app, or looking up directions on the fly, cause someone just told you about a hot new bar, restaurant or club, you need data to function. I mean how many times have you ended up somewhere you probably shouldn’t be and needed to call an Uber asap to come get you? For us, we use Fido’s #FidoRoam package which allows us to continue using our data when we travel as if we are home for just $5, instead of paying $85 for some unbelievably paltry 250 mbs. This is an absolute travel necessity.