Blown Away by the Windy City: Chicago on a Shoestring

Chicago. They call it the Windy City, but despite popular belief, the reference actually harkens back to the time when ‘Windbag Politicians’ took over the 1893 World Fair. That’s not to say that this city won’t blow you away, because it absolutely will. In fact, by the end of this article, I promise you’ll be penciling this roaring American town into your travel calendar. And what’s even better news is that experiencing this city – from its storied past steeped in Prohibition and Organized Crime, to the Art Deco movement, diverse culinary and musical traditions, and even the century-old ‘L’ train that keeps its people moving atop the bustling streets below – can be done right on a budget. Here’s how two broke Canadians did Chicago on a shoestring.


Upon arrival, it won’t take you long to realize that Chicago is an architectural dream – an intoxicating blend of classic, colonial, art deco and modern styles. Much like a steamy cup of Chai tea, each building’s individual essence comes together to form one bold flavour, still managing to carry its own distinguishing taste. One of the most popular ways to see the city (and a fantastic way to orient yourself to your new home-away-from-home) is a Chicago River Tour.

Chicago River Tour viewing building architechture

River tour companies are a dime a dozen in this town – unfortunately, the tours are not. Be prepared to spend about $40USD ($50CAD) for a 90 minute tour, such as the Wendalla Architectural Tour. While we loved booting around the river with our uber-knowledgeable tour guide, we didn’t love the crying babies, selfie sticks (I nearly lost an eye) and general commotion you get in a tour with hundreds of people. The good news is there are fantastic alternatives to a typical jaunt on the river. Consider using a little elbow grease to get around town – companies like Kayak Chicago rent Kayaks for $20USD ($27CAD) an hour for a single, or $15USD ($20CAD) per person for a tandem. No previous experience is required, and in the hot and humid Chicago summer, you’ll be happy to be closer to river level (just uh, keep your appendages out of that water. Trust me.)

Don’t have your sea legs? Check out the beautiful (and budget-friendly) Chicago Riverwalk, a pedestrian walkway that runs along the south bank from Lakeshore to Franklin street. Keep an eye out for the black archways above stone staircases along the river. PRO TIP: To take in the Riverfront at its quietest, and arguably most beautiful, take a walk after midnight. Though “officially” closed at 11pm, the walk is patrolled by security guards with an eye out for trouble. If you apply a little (Canadian, in our case) charm, you’ll be granted VIP access to some of the city’s most dazzling views reflected off of the river.

Walking along the Chicago riverfront at night

Chicago Riverfront          Cost: $0 – $30USD


Downtown Chicago is extremely walkable. Thanks to the Great Fire of 1871, Chicago was essentially given license to start all over (lending itself to its other nickname, ‘Second City’). The well-planned layout offers wide, majestic avenues that feel spacious, even as Chicagoites and tourists jostle by. There are a few ‘free’ walking tours, like Free Tours By Foot – Chicago which operate under a pay-what-you-can system. If you want to go the completely free-route, a little tech savvyness will set you right in a jiffy. We loved Metrowalkz Self Guided Walking Tour, a mobile-friendly site which guides you through your neighbourhood of choice, providing the history behind each location, opening and closing times, and cost of entry (if any – many and most are free). The upside? You’re in control of what you see – skip the buildings not of interest to you, and linger longer in those that tickle your fancy. Here are a few of our favourites that are open to the public and budget-friendly:

The Chicago Cultural Center

The beautiful dome inside The Chicago Cultural Center

Opened in 1897 as the Central Library Building, the Chicago Cultural Center acts as the city’s official reception venue when the Mayor welcomes guests. Upon entering the lobby, you’ll understand why – let your eyes drink in the imported marble (used by architects to say “Hey Chicago, we’ve arrived”), polished brass decals, fine hardwoods and mosaics of glass and stone that adorn the walls and ceilings; tributes to the greatest literary names the world has ever known. Climb the stairs to the gallery and take in the breathtaking Tiffany glass dome, the world’s largest, containing over 30,000 pieces of stained glass.

Inspiration from some of the world's greatest minds

Before you go, be sure to take in a few of the numerous free exhibitions that run throughout the building. We really enjoyed the Chicago in Protest exhibition on the main floor, highlighting the city’s fight for the preservation of its historical buildings (Spoiler alert: Chicago wasn’t always so dedicated to preserving its past). PRO TIP: Take advantage of the free WiFi, and Google-Map your way to your next stop.

Chicago Cultural Center         Cost: FREE

Union Station

Union Station in Downtown Chicago

If you’ve ever taken in the grandeur of New York’s Grand Central, or the decaying spectre of Detroit’s once-spectacular Union Station, then you can’t miss Chicago’s card-in-the-game, its own magnificent Union Station. As travelers, we all feel our hearts skip a beat with the energy and potential of the great ‘perhaps’ when we enter a travel hub, such as Union Station’s Great Hall. Currently home to the city’s Amtrak station, it’s 110-foot walls, vaulted ceiling, gilded lamps and sweeping balconies take you right back to the Roaring 20s, when travel was a down-right luxury. During WWII, this station welcomed over 100,000 passengers a day, many of whom were soldiers heading off to war, never to return.

Follow the ‘To Trains’ signs to take in a free exhibition, which offers a diverse history of the site, including many of the now-famous movies (The Untouchables, anyone?) filmed at this incredible location.

Union Station        Cost: FREE

The Pittsfield Building

Step into 1920's splendor with this spectacular art deco building
Step into 1920s splendor in this spectacular Art Deco building

This hidden gem is tucked away among the hustle and bustle of Washington Ave. Dwarfed by the massive Marshall Fields (now Macy’s) building across the street, and sandwiched between a modern day shopper’s paradise, walking into the lavish lobby of The Pittsfield Building is akin to stepping into a time machine. Once the tallest skyscraper in Chicago, the immaculately preserved 1920s-era office building drips with gold decor. The points and angles of Art Deco decor dot each nook and corner, juxtaposed against stark Gothic-style columns. As you walk through the lobby, you practically feel your trekking shorts melt away into a sashaying flapper dress or a dapper suit. I mean, what was the last office building you saw crowned with a five-story chandelier?

 The Pittsfield Building     Cost: FREE


Escape to this garden oasis while still admiring the cityscape
Escape to this garden oasis while still admiring the cityscape

No piece on Chicago would be complete without mentioning Millennium Park. Built on a site that was controlled by the Illinois Central Railroad for almost 150 years, the park is seen by many Chicagoans as the crowning glory of their city, and for good reason. The 24.5 acre public green space offers up state of the art facilities (like the Jay Pritzker Pavilion, a bandshell that seats up to 11,000 people), unique public artwork and stunning gardens.

 Grant Park Symphony Orchestra and Chorus, free on weekends

We were lucky enough to catch a free concert by the Grant Park Symphony Orchestra and Chorus – the nation’s only remaining free, municipally supported, outdoor classical music series – and auditory proof that Chicago loves its citizens. Drink in the haunting notes of Mozart of Haydn as you stretch out in the grass. PRO TIP: Make friends with a local who will likely have an adult beverage or two on hand, as the park allows citizens to bring alcohol and food within bandshell limits during performances.

Other notary must-sees are Buckingham Fountain (AKA The ‘Married With Children’ fountain for the 80s & early 90s generations), The Crown Fountain, a unique video sculpture featuring the faces of thousands of Chicago citizens of every age, and of course the Cloud Gate, lovingly referred to as ‘The Bean’ by locals and tourists alike.

The Cloud Gate (AKA 'The Bean') is the crowning glory of Chicago's art installations

(Note: We were going to avoid that whole ‘bean’ situation altogether, passing it off as “the thing the tourists do”. When we arrived, however, we were completely astounded by this massive, silver, hovering thing that reflects the city skyline like some celestial object dropped from space. It will lure you like a magnet, and keep you transfixed. It’s also a hell of a place to people watch. So go)

You can easily spend an entire day taking in the public art displays and stopping to smell the flowers in this massive public green space, and I highly recommend you do.

Millennium Park      Cost: FREE


Diners & Dives: The Pittsfield Cafe

You won’t be disappointed by the diner-style eats at The Pittsfield Cafe, located in the lobby of the aforementioned Pittsfield Building. Step into the cafe and you’re transported to the American diners of the 50s and 60s, a la Route 66. In fact, you couldn’t get more Americana unless a Bald Eagle landed in your eggs and pooped the stars and stripes.

The joint is family run, with 2 generations at the door. ‘Pops’ will great you with a smile, then send his son over to do the dirty business of seating you. Enjoy all-day breakfast options, like the filling-yet-economical ‘PC Muffin’ – an egg sandwich topped with American Cheese – at an economical $3.99USD ($5.50CAD). Or splurge and order ‘The Sampler’ – eggs, hash and bacon with easily the 2 best pieces of French Toast this girl has ever savoured. For less than $10USD ($13CAD), you’ll be crusin’ on deliciousness until dinner time. PRO TIP: They are closed on Sundays. We found out the hard way.

The Pittsfield Cafe     Cost: $4 – $10USD

Snack Attack – Chicago Food Trucks

Creamy Confections c/o Firecakes Donuts
Creamy & Crunchy Confections c/o Firecakes Donuts

Like many cities all over the world, Chicago has embraced the food truck frenzy, bringing its diverse culinary traditions to the streets. With municipal restrictions recently lifted on what food can be sold and where trucks can park, a good snack is never far away. Using the Chicago Food Truck Finder App (available online and for free download from the app store), we tracked down Firecakes Donuts. Operating out of a vintage ’68 Citroen truck named Billy, Firecakes offers up freshly baked, small-batch donuts of the staple kind, like honey glazed, classic jelly, and old-fashioned buttermilk. We opted for the award-winning Vanilla Iced (ice baby). Pillowy, melt-in-your mouth dough topped with crunchy confections, the $2.50USD ($3.35CAD) treat was easily the size of my head and was more than enough satisfaction for two to share.

Food Trucks     Cost: $2.50 – $10USD

 Dinner Time – Mexican, Italian and more…

When eating out in a city, dinner is easily the most expensive meal of the day. Add to the fact that you’re in ‘murica, and chances are the portions size will blow not only your budget, but also your waistline. With a little research ( should be among your best travel companions), we discovered affordable dining spots like Su Casa, a charming, borderline-kitschy Mexican restaurant in the “oh you fancy” part of town. Take in the colourful atmosphere, enjoy the freshly baked and complimentary nachos and authentic (re: hot as hell) salsa while you peruse the menu of Mexican staples. We enjoyed a sharable plate of overstuffed Shrimp Chimichangas on a bed of rice for only $15USD ($17.25CAD).

Want to channel a little Alphonse Capone, but stay on budget? Seek out this hidden diner north of the garish Trump tower. The charming Bongiorno’s Italian Deli & Pizzeria is a little piece of Italy on the riverfront, offering up classic red and white-checkered, alfresco-style seating. For less than $20USD ($27CAD), enjoy an entree-sized salad, like the Prosciutto E Mozzarella with freshly baked bread, and a 10” thin crust specialty pizza. Sharing is encouraged at this family-run business where every bite is made with love.

Italian decadence for a steal, Biogornio’s is fantastic for an alfresco lunch or dinner

Bongiorno’s Italian Deli & Pizzeria       Cost: $10USD – $20USD


Sights and Sounds at Navy Pier

Night time is the right time to see the city in all its dazzling glory. If you’re not against hob-nobbing amongst the tourist crowd, take a stroll along Navy Pier for some bang-up views of the waterfront and an extraordinary view of the twinkling Chicago skyline.

Navy Pier in Chicago at dusk

Be sure to go on a full stomach (see food tips above) as the chain-restaurants are pricey and oh-so-generic. If you’re in the city in late summer, consider bringing your own bagged popcorn for Movies On The Pier, offering up classic blockbusters free every Thursday evening at 8pm during August and September. Or take in a spectacular Fireworks Show over Lake Michigan on Wednesdays and Saturday evenings. Boat tour companies offer Firework Cruises, but take it from us, the view from the pier is superb (and free!).

Navy Pier     Cost: FREE

Eat, Drink & Be Merry at Logan Arcade

Want to go where the locals are? Just ask one. We learned pretty quickly that Chicagoans are fiercely proud of their city, and with just a little probing, we were soon blasting across the city via the CTA Blue Line ($3USD per ride) to Logan Square, a hip uptown suburb where hole-in-the-wall diners meet antique shops, farmers markets and public art exhibitions. A few blocks walk from Western station sits Logan Arcade, a holy mecca for any 80s & 90s kids that grew up with the likes of Frogger, Rampage or Tron, just to name a few. With over 40 original, vintage video games and 25 pinball machines, as well as a fully stocked bar with many local craft brews on offer, we were soon flitting from one machine to the next, smiling so hard our faces hurt. With no cover and drink specials such as PBR cans for $1.50USD ($2CAD), one can easily drink, game and be merry for hours on end on a $20 bill. PRO TIP: Keep your eye out for free events like their Tuesday Pinball tournaments, Classic Movie Nights and community-sponsored events. We were luckily enough to attend the Vegan Food Fest, nibbling on delicious treats like tacos, humus and rich, moist brownies topped with bourbon peanut butter sauce – all free for the takin’. Visit the website or follow them on social media for the event du jour.

Vintage games, local craft brews and free food = hours of fun

Logan Arcade     Cost: Approx $20USD

…And All That Jazz: The Green Mill

Prohibition era charm meets musical perfection at The Green Mill
Prohibition era charm meets musical perfection at The Green Mill

With Chicago being one of the world’s biggest jazz destinations, it would be downright criminal not to take advantage of the opportunity to see some of the scene’s most talented musicians, up close and personal. On Chicago’s North Side, the dazzling bulbs of The Green Mill Cocktail Lounge sign will lure you in with its old world appeal. Packed to the gills with music lovers of all ages, from hip 20-somethings to sophisticated gray hairs, a 1940s area jukebox cracks and warbles notes of trumpets and saxophones over the din of mingling spectators. At the bar, pictures of Al Capone and Frank Sinatra, both previous patrons, watch over the martini-sipping crowd as the band cues up. Seating is limited, but a quick smile and hello in the direction of some locals resulted in an invite to share a primo booth. A word to the wise: prepare to be shamelessly shushed by the crowd (or the ever-present, leatherclad doorman) if you talk or whisper during the performance. Trust us – just close your eyes and take in the magic. PRO TIP: Avoid the hefty $15 cover at the door – arrive after midnight and pay just $5USD ($6.75CAD), or after 2am for no cover.

The Green Mill     Cost: Free – $15USD

Chicago might be one of the most expensive cities in North America, but like most travel destinations, with a little research and gumption you can do it right AND save your bank account in the process. This article touches on just a small sample of what this great city has to offer, so I do hope you have a chance to stop by and explore on your own. Got any Chicago tips of your own? Please add them below!

Happy Travels!
Happy Travels!