The Ultimate Travel Girl’s Guide to Chicago

A picture of a neon sign with the word Chicago in bright lights

Often overshadowed by New York or Boston, Chicago is deserving of its own recognition as a top U.S. City break. With world-class restaurants and a thriving historic blues and jazz scene, this lakeside city comes alive for visitors in an authentic way. With the extra bonus of being close to the Canadian boarder and halfway between Dallas and Boston, Chicago is perfectly located for a road trip or short flight.

A turquoise Chicago River is surrounded by sky scrapers

Here's my ultimate travel girl's guide to Chicago:

How To Get There

Fly: O’Hare international airport is a 45 min train ride from downtown for 5$ ( take the  Blue line L train) or a 20 min taxi ride, which will cost about $40.

Drive: Chicago is a very drivable city and makes for the perfect road trip destination. Parking can be expensive, so check online in advance for parking options.

Train: Chicago is on the Amtrak route, making it accessible from Toronto as well as many locations across the U.S.

What To Do

Go to a Blues/ Jazz Club: Chicago boasts a rich musical history which developed into its own style of Blues and Jazz. Step into Blue Chicago, Buddy Guy’s Legends or B.L.U.E.S for some of the best live blues in town.

SUP/Kayak the Chicago River: See a different side of the city by exploring from the water! Urban Kayaks on the banks of the river lets you rent stand up paddle boards or kayaks by the hour. Paddle past the towering wall of skyscrapers for a truly unique experience!

A man and a woman stand on a bride with a turquoise Chicago River in the background surrounded by skyscrapers

Explore the Chicago Zoo:  A wonderful free zoo with beautifully landscaped gardens, a wide selection of well-treated animals and indoor greenhouses.

Visit the Navy Pier: a pier lined with restaurants and shops, complete with a Ferris wheel for a bird’s eye view of the skyline!

A blonde woman takes a picture of Chicago navy pier in the distance

A blonde woman stands with her arms open at the are of a Ferris wheel

Stroll Through Centennial Park: I have to admit that before visiting Chicago I didn’t see the draw of the bean, but I was impressed! The park itself is impressively designed to balance quiet natural seclusion, art installations and city views.

A man gazing into the silver bean with the skyline reflected in it

See a Baseball Game: I’m not the hugest sports fan ( as in not at all), but decided to give this iconic stadium a try. Baseball has been an essential part of Chicago life since 1914 and standing in the stand among the thousands of cheering locals felt like a true Chicago experience.

A blonde woman sipping a large drink with a Toronto blue jays base ball cap on in a stadium

We were cheering for the wrong team, sorry Chicago!

Shop the Magnificent Mile: A street lined with shops ranging from high-end designs to your favourite chain stores. Don’t forget to explore the side streets for a quieter ( and cheaper) place to eat.

Sip Cocktails at a Rooftop Bar: With the worlds first skyscraper built here, what better way to enjoy the skyline than by sitting among them?

A fancy orange cocktail perched on a a bar with the Chicago skyline in the background

A picture facing upwards looking at the sky and two large sky scrapers

What to Eat

Hotdog:  Topped with mustard, white onions, sweet pickle relish, dill pickle, pickled sport pepper and celery salt. Do not, I repeat, do not ask for ketchup or you’ll shock and horrify every local within earshot.

Popcorn: A mixture of cheddar cheese and caramel this sweet and savoury mix will become your next addiction. You’ve been warned.

Deep Dish Pizza: Any pizza lover has to give deep dish a try! Although I prefer New York Style (sorry Chicago), deep dish definitely has it’s merits and needs to be tried at least once.

Craft Beer:  Chicago has a booming local brew scene that has beer fans travelling far and wide to have a taste. I’ll admit that I’m not a beer fan, I’m more of a cocktails and bubbly girl, so I didn’t sample any myself.

Where to Stay

Chicago is a wonderful city for walking, so try to take full advantage by staying in the Chicago loop. This will have you in the heart of downtown and within walking distance or a quick transit ride away from anything you want to see.

Tips and Tricks

It really is the Windy City, so be warned if wearing hats or dresses. Some poor, unsuspecting passers-by got an eye full of more than they wanted to see on multiple occasions. Also, pack a sweater even in the summer as nights can get chilly.

Visited Chicago recently? Tell us about it below!

Leave a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.