24 Hour Stopover: Chicago, Illinois

Canadians wait so long throughout our winter months for the weather to warm up. So when spring finally hits, I start daydreaming about a getaway not too far from home.

If you’re city hopping, then add Chicago to your list! Chicago has a big city feel; but at the same time, it’s laidback, down-to-earth and unpretentious.

Known for its architecture (home to the world’s first skyscraper), Chicago has so many things going for it in addition to its unique buildings. Spend a long weekend there and get wooed by Chicago’s killer music scene, get lost wandering along the Chicago River Riverwalk and one of Chicago’s 77 diverse neighborhoods, or spend your days overdosing on great food and sunshine on one of the 26 miles of public beaches along Lake Michigan.

Here are some ideas on how making the most of 24 hours in Chicago:

9:00am: Get Acquainted With the City

Historic guided tours can be a great way to start your trip and orientate you to a city.  Most often they are led by passionate locals who give you a unique insider’s perspective that’s both rich in history and peppered with tips on the best spots in the city.

A great option for budget conscious travellers is Free Tours by Foot.  As the name suggests, there is no set cost to the tour, you simply pay what you feel it was worth at the end. They offer a really great selection of fun tours that cover a lot of the Chicago highlights and knowledgeable guides that offer tidbits of information you just can’t get from a guidebook.

Take in the city from a different viewpoint by boarding a boat for an architectural tour along the beautiful Chicago River. Surrounded by skyscrapers, you will leisurely glide along the waterway while hearing stories about the beginnings of the city, its architecture and noteworthy buildings. This tour is really interesting and well worth the ticket price.  There are several different operators including a very popular and recommended cruise by the Chicago Architecture Foundation.

For sports fans, a tour of the second oldest ballpark in America is a must.  Set right smack in the middle of a neighbourhood and famous for its ivy-covered outfield walls, Wrigley Field is home to the Chicago Cubs and one of the last manually operated scoreboards. Go behind the scenes, including inside the press box, the Cubs’ locker room and dugout (on non-game days) while hearing fascinating stories along the way.

2:00pm: Get Your Bum to the Beach

Spend a well earned afternoon chilling by the beach after a morning of sightseeing. Start by popping by Cloud Gate (aka The Bean). This oh-so-cool outdoor stainless steel sculpture reflects a distorted yet beautiful panorama of its surroundings. Visiting The Bean is worth fighting the selfie loving, snap happy crowds who swarm it.

Next, take a walk North up Chicago’s Magnificent Mile, an avenue bursting with shops, over 275 restaurants and eye-catching architecture. Linger around one of my favourite buildings in the city, the Tribune Tower. Take a peek inside its ornate lobby and walk around its exterior where you’ll spot 149 different bits of rock from historical sites around the world. See if you can spot a piece of the Great Pyramid, a brick from the tomb of Abraham Lincoln or part of the Great Wall of China.

Then, switch gears and rent a Divvy city bike to take a scenic ride along the edge of Lake Michigan on the Lakefront trail.  Keep peddling until you reach the super popular and very well maintained North Avenue Beach.  Soak up the sun, take a swim, or play a round of volleyball if you still have some energy. Chicago has 26 miles of public beaches, if North Avenue Beach is too crowded for your pleasure, you’re sure to find another one that fits your style.

4pm: Take in Great Views of the City

For my favourite view, scoot up to the 96th floor of the John Hancock Tower.  Skip the pricey Observation Deck and grab a drink or dessert at Signature Lounge instead.  Enjoy 360 degree jaw-dropping views of the sprawling city below and sparkling Lake Michigan. With floor to ceiling windows all around you, you’ll feel like you’re on top of the world! Ladies, be sure to make a stop at the loo for the best view I’ve ever seen in a bathroom (sorry gents!).  If heights make you queasy, you can get a pretty view of the skyline from Lincoln Park Zoo (it’s free!) all while keeping both feet on the ground.

For the nostalgic traveller, ride the Ferris wheel at Navy Pier for a fun and exhilarating view of the famous Chicago skyline. Standing at 150 feet, it’s a replica of the very first Ferris wheel which was built in 1893 for the Chicago World’s Fair.

7pm: Re-Fuel With Great Eats

Chicago is known for its culinary scene and there is an endless list of places you can get a good meal. Here is a very small sample of some of the places I’ve enjoyed.

For a seafood fix, head over to Shaw’s Crab House for a vast selection of succulent plates from chowder to fresh fish, oysters, shrimp, scallops, Maine lobster and Alaskan King Crab. If you really want to spoil yourself, try the Surf & Surf – chilled Alaskan golden king crab legs and an 8oz main lobster tail.  It’s got a hefty price tag on it, but it’s to die for! I love eating in their Oyster Bar which has a relaxed, retro diner vibe to it. Made other dinner plans? Pop by for half price oysters from 4-6pm for an appetizer.

For pizza: Chicago is home to the infamous deep dish pizza; a thick pizza baked in a pan with a crispy butter crust, thick layers of flavourful toppings and loads of gooey cheese.  Knife and fork required! One slice alone will probably meet your daily caloric intake, but after a full day of sight-seeing, I like to think I’ve earned it, no? Chicagoans have varying opinions on which is establishment is the best place for deep dish. If your stomach can handle it, why not try a couple different places? My picks include Lou Malnati’s Pizzeria and Uno Pizzeria & Grill.

Sweets & Treats: Satisfy your sweet tooth at Garrett’s Popcorn Shop. A Chicago original, Garrett’s has been popping gourmet popcorn in old-fashioned copper kettles since 1949. If you like it sweet and savory, try their famous Garrett Mix, a blend of cheese and crispy caramel corn. For a real indulgence, opt for their caramel crisp corn with almonds, cashews, macadamia nuts or pecans. Keep an eye out for their sinful (in a good way) seasonal blends. Take a bag home and keep it close, you won’t want to share this treat.

9:00pm: Spend an Evening with the Blues

It would be an absolute sin to leave Chicago without spending at least one night at a Blues Club. Chicago has a world renowned vibrant blues scene. With a long list of popular and recommended music venues you can choose from, you probably can’t go wrong with any of them. Expect to see raw, face-melting performances and guitar solos from seasoned Blues legends and local up-and-coming talents at open mic nights.  You are guaranteed a memorable night out and you’ll also bump into some interesting characters along the way.

Hit up Kingston Mines for a down and dark vibe and live music playing until 4am (not to mention great BBQ ribs for a late night snack!).  Another favourite is Buddy Guy’s Legends for more of a club-like feel; you may even catch a performance by Buddy Guy himself.

2:00am: Catch Your Zzz’s

After a full day out and about, nothing feels better than kicking off your shoes and curling up under the covers of a cozy bed. Try Hotel Felixfor a centrally located and eco-friendly option (their carpets are made of recycled soda bottles!). Hotel Felix welcomes you with friendly staff, clean and comfortable rooms allowing for a restful night’s sleep to recharge and prepare you for the next day’s adventure.