Chicago, United States
The Loop & River North · Architecture, museums & deep-dish · Direct flights from Canada
4.7 · 9,000+ Chicago city breaks booked by Canadians
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City Break Packages to Chicago
3-night downtown hotel stays with return flights from Canada
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Hotels in Chicago
Downtown Loop, River North and Magnificent Mile stays
Breakfast IncludedSuper 8 By Wyndham Morton Grove/Chicago
Morton Grove
2.0
- Restaurant
- Breakfast
- Lounge
- WiFi
From
$133/ night
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Harvey
3.0
- WiFi
- Parking
- Elevator
From
$154/ night
Breakfast Included
Breakfast IncludedCourtyard By Marriott Chicago Deerfield
Deerfield
3.0
- Pool
- Restaurant
- Breakfast
- Bar
From
$181/ night
Delta Hotels By Marriott Chicago Willowbrook
Willowbrook
3.0
- Pool
- Restaurant
- Breakfast
- Bar
From
$182/ night
Courtyard Chicago Elmhurst/Oakbrook Area
Elmhurst
3.0
- Pool
- Spa
- Restaurant
- Breakfast
From
$230/ night
Breakfast IncludedHampton Inn & Suites Rosemont Chicago O'Hare
Rosemont
3.0
- Pool
- Golf
- Restaurant
- Breakfast
From
$265/ night
At a glance
Everything you need to know about Chicago
Chicago is America's architectural showpiece — a bold skyline of glass towers rising off Lake Michigan, threaded by the Chicago River and its famous Riverwalk. Base yourself in the Loop or River North and you're steps from Millennium Park and Cloud Gate ("The Bean"), the Art Institute, Navy Pier, deep-dish pizza institutions, blues and jazz clubs, and the Magnificent Mile's shopping. It's a big, walkable, four-season city with an unbeatable public-transit "L".
Chicago, IllinoisClimate
Climate
-5–29°C · four-season lakefront climate
JanDec
PeakShoulderAvoid
Warm summers by the lake are ideal; winters are cold and snowy — great for indoor museums and pubs.
Currency
US Dollar
1 CAD ≈ 0.73 USD · cards accepted everywhere
Entry
Visa-free
Valid passport; no visa or ESTA for Canadians by air
Top Experiences in Chicago
DowntownMillennium Park & Cloud Gate
Snap the mirrored Cloud Gate ("The Bean"), catch a free concert at the Pritzker Pavilion, and stroll to the lakefront Maggie Daley Park.
On the waterArchitecture River Cruise
Glide the Chicago River past skyscrapers with a guide from the Chicago Architecture Center — the city's signature experience.
CultureArt Institute & Museum Campus
See the Art Institute's Impressionist icons, then the Field Museum, Shedd Aquarium and Adler Planetarium on the lakefront campus.
Essential info for Canadian travellers
Passport & entry: Canadian citizens travelling to the US by air need only a valid passport — no visa or ESTA is required.
Currency: The US Dollar (USD) is used everywhere. Cards and tap-to-pay are widely accepted; keep small bills for tips and taxis.
Power & plugs: The US uses 120V/60Hz with Type A/B plugs — the same as Canada, so your devices work without an adapter.
Time zone: Chicago runs on Central Time (CT) — one hour behind Toronto year-round.
Getting around: The CTA "L" trains and buses cover the city cheaply; the Blue Line links O'Hare and the Orange Line links Midway to the Loop. Winters are cold, so pack layers.
Best time to visit Chicago
May – JunPeak season
Warm days, blooming parks and the start of festival season along the lakefront.
Jul – AugPeak season
Hot, lively summer with beaches, street festivals and Taste of Chicago — busiest and priciest.
Sep – OctShoulder season
Crisp, colourful autumn with thinner crowds and better hotel rates.
Nov – AprCold & quiet
Cold, snowy winters — ideal museum weather and the cheapest downtown hotel deals.
Where to stay
Chicago neighbourhoods
Where you base yourself shapes your trip — from the skyscraper canyons of the Loop to gallery-lined River North and the boutiques of the Magnificent Mile. Here's how to choose.
The Loop
Downtown core
The business and theatre heart of the city, ringed by the elevated "L" and steps from Millennium Park, the Art Institute and the Riverwalk.
Best for
- First-timers
- Sightseeing
- Transit access
River North
North of the river
Chicago's gallery and restaurant district, packed with rooftop bars, deep-dish landmarks and clubs, just across the bridges from the Loop.
Best for
- Foodies
- Nightlife
- Couples
Magnificent Mile & Streeterville
North Michigan Ave
The famous shopping stretch of North Michigan Avenue, close to Navy Pier, the lakefront and the John Hancock (875 N. Michigan) views.
Best for
- Shopping
- Families
- Lake views
West Loop
West of downtown
A converted warehouse district built around Randolph Street's Restaurant Row and Fulton Market — buzzy, design-led and better value.
Best for
- Foodies
- Design lovers
- Value
Beyond the city
Day trips & excursions from Chicago
Chicago is a great base for the Midwest's lakeshores, dunes and river towns. Every excursion below can be booked through ShopTravel or your hotel tour desk.
National ParkIndiana Dunes National Park
Full day · 8 hrs~80 km southeast · 1 hr by car or South Shore train
Climb rolling sand dunes and walk Lake Michigan beaches with the Chicago skyline shimmering across the water.
Insider tips
- Take the South Shore Line car-free
- Bring layers — the lakefront is breezy
City EscapeMilwaukee, Wisconsin
Full day · 9 hrs~150 km north · 1.5 hrs by Amtrak Hiawatha
Tour the Harley-Davidson Museum and the striking Milwaukee Art Museum, then sample the city's legendary breweries.
Insider tips
- Book the Hiawatha train ahead
- Time your visit for the museum's wing 'flap'
NatureStarved Rock State Park
Full day · 9 hrs~150 km southwest · 1.5 hrs by coach
Hike wooded canyons, sandstone bluffs and seasonal waterfalls above the Illinois River — a favourite Chicago outdoor escape.
Insider tips
- Waterfalls are best after spring rain
- Wear proper hiking shoes
Lake TownLake Geneva, Wisconsin
Full day · 8 hrs~120 km northwest · 1.5 hrs by coach
A genteel resort town on a glacial lake — take a mailboat cruise past historic mansions and stroll the 34 km shore path.
Insider tips
- The mailboat tour books up fast
- Great in summer and for fall colour
● Limited availability — book now
Your Chicago city break awaits
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Good to know
Chicago travel FAQ
Everything Canadian travellers ask before booking
Do Canadians need a visa for Chicago?
No. Canadian citizens travelling to the US by air need only a valid passport — no visa or ESTA is required.
How long is the flight from Canada to Chicago?
Direct flights are about 1 hour 45 minutes from Toronto to Chicago Midway (MDW), with direct service from several Canadian cities.
When is the best time to visit Chicago?
Late spring through early fall (May–October) has the warmest weather and most festivals. Summer is busiest; winters are cold and snowy but cheapest.
How do I get from the airport into the city?
From Midway (MDW) take the CTA Orange Line into the Loop in about 25 minutes; from O'Hare use the Blue Line. Rideshares and taxis are also easy.
Is Chicago easy to get around without a car?
Yes — the CTA "L" trains and buses cover the whole city cheaply, and the downtown neighbourhoods are very walkable. You won't need a car.
What day trips can I take from Chicago?
Popular options include Indiana Dunes National Park, Milwaukee, Starved Rock State Park and Lake Geneva — several are reachable by train.
What currency should I bring?
Chicago uses US Dollars (USD). Cards and mobile pay are accepted everywhere, but keep small bills for tips and street food.
Can I book excursions through ShopTravel?
Yes — you can add day trips like the Architecture River Cruise or Indiana Dunes to your booking at checkout.