Chicago things to do and where to stay

Travel Chicago

Before you even hit downtown, with its iconic architecture, refreshing green space and the Chicago River that sprawls through the city’s centre, you’ll start to imagine sinking your teeth into a deep dish pizza, a hot dog loaded with all the fixins, or maybe some delicious BBQ pork.

Whatever you’re craving, Chicago probably has it, from international cuisine and comfort food to satisfy every palette to eye-popping sites like the sprawling lakefront, live theatre scene, family entertainment, parks and shopping galore. Of course, there’s also the famous Wrigley Field, where you can spend an afternoon taking in a game.

Luckily, exploring Chicago on a budget is very doable – if you know which expenses are worth it, where to grab cheap eats and discounts, and how to use the robust public transit system to get around.

Chicago things to do and where to stay


Chicago sits on the southwest shore of Lake Michigan in the state of Illinois.

Many think the nickname “Windy City” refers to the frigid breezes that blow in off the lake to sweep through the city’s streets, but there are also references that it had a double meaning and also functioned as a metaphorical jab to supposedly boastful citizens.

Visit Chicago during spring or fall for comfort and affordability

For the most affordable accommodations and comfortable temperatures, Passion Passport suggests booking your trip during its shoulder seasons: April, May, September, or October. If you’re okay with cold temps, try early or mid-December – holiday festivities are on, hotel prices more reasonable and the glut of tourists has left.

Bonus: Airfare drops in October and November as well. Watch for cheap flights and book your plane ticket about two months before your visit.

Stay at a hostel or rent an Airbnb

If you’re going to spend most of your time discovering the city, why throw down for an expensive hotel room? You have options when it comes to affordable places to stay during your visit, including the eco-friendly HI Chicago, The J. Ira and Nicki Harris Family Hostel mentioned by Little Things Travel. There, you’ll pay $30 a night and score free amenities like wi-fi, breakfast, sheets, towels and guided tours of the city.

You can also go the Airbnb route and stay in a beautiful apartment or loft – lots of beautiful spaces are available for between $50 to $80 CDN per night.

Check out TimeOut’s guide to amazing Airbnb Chicago homes you can rent.

Chicago things to do and where to stay

Visa and passport  info

Make sure you have your Canadian passport or a valid NEXUS card if you’re flying into Chicago. In most circumstances, the Government of Canada says Canadian citizens do not require a visitor, business, transit or other visas to enter the United States from Canada but there are some exceptions.

Hop on the bus, train or subway

You’d better have a great public transit system if you have to move 2.7 million people around a city with a river running through it. Here, Chicago doesn’t disappoint – you can get around the city easily via bus, train, subway and on foot (depending on where you need to go).


Flying into Chicago, you’ll land in one of two international airports:

O’Hare International Airport

Seventeen miles from downtown Chicago, O’Hare is one of the busiest airport hubs in the country and offers restaurants, stores, boutiques, an indoor urban garden, rooms for nursing mothers and more. You’ll also find power stations and unlimited free wi-fi throughout.

Midway International Airport

Just ten miles from downtown Chicago, you’ll find a wide variety of dining, amenities and shops, rooms for nursing mothers and more at Midway, plus unlimited free wi-fi.

Choose Chicago has a great guide to these two airports, and you can check Skyscanner to compare airfare prices for both (sign up for email alerts to know instantly if the price rises or falls.)

Chicago things to do and where to stay

Public transit

Public transit here is superb – you can walk, ride a bike or use buses or trains.

Y Travel Blog suggests taking Chicago Transit Authority’s ‘L’ for most places you’ll want to go (The CTA and Choose Chicago have published helpful guides to navigating the train system).

Tip: The ‘L’ is now an official name for Chicago’s train system. It was originally short for “elevated”. – Chicago Transit Authority 

The Blue Line runs 24 hours from the O’Hare Airport to downtown Chicago. Travel bloggers Nick and Dariece over at Goats on the Road say you’ll have a 40 to 45 minute ride for $5 (less if you have an unlimited ride pass – pick these up at the airport and at vending machines throughout the city.) Arriving at Chicago Midway International Airport? The Orange Line will get you to the downtown loop area in 20 to 25 minutes.

Buses and trains use the CTA card fares of $2 and $2.25. for one fare, you can transfer twice in a two-hour period. You can also purchase a Ventra Card at stations, retail stores or online.

Chicago things to do and where to stay

Pick up a deep dish pizza, seafood tacos or Japanese fare

Once you’ve hopped off the train, it’s time to head into town for some delicious eats. Whether you came to Chicago hoping to expand your horizons or indulge in some classic comfort food, you’re in luck; the city is home to restaurants, pubs, and vendors that cater to every palette.

If you’re hoping to indulge in a little (or a lot) of deep-dish style pizza, go to Pizzeria Uno. You might wait a while but this will be worth it – here’s the place where the original deep-dish style pizza was invented! If the line is too long, move on to one of the other best Chicago deep-dish style pizza places.

Looking for a greasy spoon? Head to White Palace Grill, a legendary spot open since 1939 that’s on Vice’s Munchies list of Chicago’s 11 best cheap eats. It serves classic American diner food 24 hours a day, seven days a week.

On one of those nights when you’re hankering for something a little less traditional, go to BIG & little’s for standout seafood tacos, suggests Chicago Eater. Finally, if you’re looking for something spicy, try Ramen-san, where you can get a dish of delicious, authentic Japanese ramen, highly recommended by Chicago-based chef Grant Achatz on Eat Sip Trip.  

See iconic architecture, head to Navy Pier, see a show and more.  Chicago is full of adventures to take, whether you’re looking for something to keep the kids busy, a couple taking a whirlwind tour of this amazing city, or a group of friends taking it easy.

Chicago things to do and where to stay

Pick up a Chicago CITYPASS

First, get yourself a CityPASS, which gets you a 51% discount on VIP admission to some of the most iconic attractions in the city and lets you skip ticket lines. At the time we checked in January 2019, adult passes (ages 12+) were $147.73 CDN and child passes (ages 3 to 11) were $124.04 CDN. It’s valid for nine consecutive days starting with the first day you use it. The CityPASS will get you into:

  • Shedd Aquarium – Priority Entry
  • Skydeck Chicago – Fast Pass
  • Field Museum – VIP Entry
  • Adler Planetarium – VIP Entry OR Art Institute of Chicago – Fast Pass
  • Museum of Science and Industry OR 360 Chicago Observation Deck – Express Entry
  • Hop on a Chicago Architecture Foundation Boat Tour

Though you can walk through downtown and get a glimpse of Chicago’s many stunning skyscrapers from the sidewalk, you can’t see them in their entirety. According to TravelingMom, the 90-minute Chicago Architectural Foundation’s River Cruise is “a beautiful slow boat ride through downtown Chicago, past the city’s iconic buildings.”

This isn’t a tour where someone drones on and on in terms you can’t understand. Instead, expect to learn how the city’s architecture interweaves with history, politics, business and art. Bonus: The eye-popping photos you’ll post on Instagram!

Some of the iconic buildings on the list include:

  • Marina Towers (which has appeared in dozens of movies)
  • The 110-story Willis Tower, one of the tallest buildings in the world
  • The massive former Chicago Post Office
  • The rounded residential units of River City

From gothic to contemporary, art deco, mid-century modern and more, you’ll see it all here. TravelingMom documented their experience and has some compelling reasons to spend the $46 for a daytime cruise or $49 for a twilight cruise at 7:30 p.m. Note: Purchase your tickets in advance to avoid disappointment.

Explore Navy Pier

Another iconic spot you don’t want to miss, Navy Pier is just over 100 years old and offers 50 acres of unforgettable attractions, experiences and cultural wonders.

In fact, travel blogger Nomadic Matt described it as “a carnival in the city”, with a huge Ferris Wheel, rides and games, theatres, a children’s museum, shopping, restaurants, and more.

Note: There is no admission fee to enter the pier itself, but individual attractions may have admission prices. The pier is closed on Thanksgiving and Christmas.

Stroll or bike along the Chicago lakefront

Need some fresh air? Rent a bike (or just walk) and explore the Chicago Lakefront Trail. See the popular Montrose Beach,  the scenic Belmont Harbor in the Lincoln Park  neighbourhood, Lincoln Park Zoo, Millenium Park (which isn’t directly on the trail but close enough that you can lock up your bike and take a detour), and the Museum of Science and Industry.

Splinster has a definitive guide to cycling the Chicago Lakefront Trail you’ll want to check before heading out.

Chicago things to do and where to stay

Check out the live theatre scene

The Chicago Theatre is a historic attraction the city is known for. When you first walk up to this iconic national landmark, you’ll probably immediately recognize its six-storey high marquee, which shows up almost any time the city is mentioned.

Built in 1921 and located in downtown Chicago, the French Baroque style theatre features a five-storey lobby. It was the first lavish movie palace in America. As Choose Chicago notes, “comedy legends, rock world tours, acoustic sets and more are all at home in this incredible venue. If you want to see C-H-I-C-A-G-O, this is the place.”

Shop Michigan Avenue’s Magnificent Mile

If you love to shop, Chicago is for you. Techies, fashionistas and bargain hunters will be in heaven in Chicago’s shopping district, which includes The Magnificent Mile. Here you’ll find everything from Chanel to Giorgio Armani, Bloomingdale’s, TJMaxx, Apple and more. There are also attractions, museums, theatres, the 360 Chicago Observatory, comedy clubs, a diverse list of restaurants – almost anything your heart could desire.

Chicago things to do and where to stay

Take in a game at Wrigley Field

After you’ve shopped til you’ve (almost) dropped, take a load off and head to a Chicago Cubs game at Wrigley Field if you visit during baseball season, which runs from March to September.

From seeing the large, 1930s-era red marquee at the main entrance to grabbing some merch and seeing all the action from your seat, this is another activity to add to your list, even if you’re not a baseball fanatic. Ticket prices vary depending on section.

Travel and lifestyle blog Thyme & Love has an in-depth guide to Wrigleyville you should check out.  Chicago is an eclectic city with lots to offer everyone from sports fans, foodies, fashionistas and shoppers, families, and kids of all ages. You can visit the city on a budget and with its world-class transportation system, free sights and attractions and lots of cheap eats on offer, there’s no shortage of things to keep everyone entertained while you’re here.

Are you travelling to Chicago for the first time? Returning to a favourite destination? What are your best tips when it comes to saving for vacations? We’d love to hear what you’ve planned, or any trips we missed! Share your story in the comments and tell us what destinations are on your wish list. Our team love saving for holidays and we hope to inspire our members with exciting suggestions to spend your Caddle money.