Cheap flight deals from Chicago (CHI) to Pelee Island (null)

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Airfares from One Way, $523 Round Trip from Chicago to Pelee Island

Prices starting at $523 for return flights and for one-way flights to Pelee Island were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Jun 12 - Sun, Jun 14
ORD
Chicago
YQG
Windsor
$523 Roundtrip, found 5 days ago
$523
Roundtrip
found 5 days ago
Select Air Canada flight, departing Fri, Jun 12 from Chicago to Windsor, returning Sun, Jun 14, priced at $523 found 5 days ago
Fri, Jun 12 - Sun, Jun 14
ORD
Chicago
YQG
Windsor
$548 Roundtrip, found 5 days ago
$548
Roundtrip
found 5 days ago
Select Air Canada flight, departing Fri, Jun 12 from Chicago to Windsor, returning Sun, Jun 14, priced at $548 found 5 days ago
Fri, Jun 12 - Sun, Jun 14
ORD
Chicago
YQG
Windsor
$599 Roundtrip, found 5 days ago
$599
Roundtrip
found 5 days ago
Select Air Canada flight, departing Fri, Jun 12 from Chicago to Windsor, returning Sun, Jun 14, priced at $599 found 5 days ago
Fri, Jun 12 - Sun, Jun 14
ORD
Chicago
YQG
Windsor
$623 Roundtrip, found 5 days ago
$623
Roundtrip
found 5 days ago
Select Air Canada flight, departing Fri, Jun 12 from Chicago to Windsor, returning Sun, Jun 14, priced at $623 found 5 days ago
Fri, Jun 12 - Sun, Jun 14
ORD
Chicago
YQG
Windsor
$734 Roundtrip, found 5 days ago
$734
Roundtrip
found 5 days ago
Select Air Canada flight, departing Fri, Jun 12 from Chicago to Windsor, returning Sun, Jun 14, priced at $734 found 5 days ago
Fri, Jun 12 - Sun, Jun 14
ORD
Chicago
YQG
Windsor
$759 Roundtrip, found 5 days ago
$759
Roundtrip
found 5 days ago
Select Air Canada flight, departing Fri, Jun 12 from Chicago to Windsor, returning Sun, Jun 14, priced at $759 found 5 days ago
Fri, Jun 12 - Sun, Jun 14
ORD
Chicago
YQG
Windsor
$792 Roundtrip, found 5 days ago
$792
Roundtrip
found 5 days ago
Select Air Canada flight, departing Fri, Jun 12 from Chicago to Windsor, returning Sun, Jun 14, priced at $792 found 5 days ago
Fri, Jun 12 - Sun, Jun 14
ORD
Chicago
YQG
Windsor
$817 Roundtrip, found 5 days ago
$817
Roundtrip
found 5 days ago
Select Air Canada flight, departing Fri, Jun 12 from Chicago to Windsor, returning Sun, Jun 14, priced at $817 found 5 days ago
Fri, Jun 12 - Sun, Jun 14
ORD
Chicago
YQG
Windsor
$911 Roundtrip, found 5 days ago
$911
Roundtrip
found 5 days ago
Select Air Canada flight, departing Fri, Jun 12 from Chicago to Windsor, returning Sun, Jun 14, priced at $911 found 5 days ago
Fri, Jun 12 - Sun, Jun 14
ORD
Chicago
YQG
Windsor
$936 Roundtrip, found 5 days ago
$936
Roundtrip
found 5 days ago
Select Air Canada flight, departing Fri, Jun 12 from Chicago to Windsor, returning Sun, Jun 14, priced at $936 found 5 days ago

Pelee Island economy flight packages

Price found within the past 48 hours. Click for updated prices.
Masquerade Tower at Rio Hotel & Casino
3.0-star property

Masquerade Tower at Rio Hotel & Casino

7.6/10 Good! (1,656 reviews)

Apr 16 - Apr 20

4 night stay

Chicago (CHI) to Las Vegas (LAS)

Frontier Airlines • Non-stop • Coach

Las Vegas (LAS) to Chicago (CHI)

Spirit Airlines • Non-stop • Coach
Price was $666, price is now $302 per person
$302
per person
found 1 day ago
We absolutely enjoyed our stay the brand new renovated Rio masquerade towers did not disappoint. We had a full-size room which was like a suite. The food options here are great. You really don’t have to leave and go on the strip because there’s so much to eat drink and enjoy at this location. It was recently taken over by Hyatt and you can tell.

Reviewed on Feb 4, 2026

Casablanca Miami Beach
3.0-star property

Casablanca Miami Beach

5.8/10 (311 reviews)

Apr 11 - Apr 18

7 night stay

Chicago (CHI) to Miami (MIA)

Spirit Airlines • Coach

Miami (MIA) to Chicago (CHI)

Frontier Airlines • Coach
Price was $1,071, price is now $529 per person
$529
per person
found 14 hours ago
Very good for the price, Right on the beach, has a kitchen, Ocean view. Very easy check-in check-out. 1 -1/2 Block from Publix supermarket. 30 minutes from Miami International Airport. Will come again.

Reviewed on Apr 8, 2025

Miami Downtown Condos
5.0-star property

Miami Downtown Condos

8.6/10 Excellent! (72 reviews)

Mar 27 - Mar 29

2 night stay

Chicago (CHI) to Miami (MIA)

Frontier Airlines • Roundtrip • Coach
Price was $2,674, price is now $1,346 per person
$1,346
per person
found 1 day ago
Staff was all very friendly. Location is close to a lot of stuff. The park and Brickell area are short walks or the Brickell loop train is across the street. Lots of dining near by. Much better than a typical hotel room.

Reviewed on Oct 31, 2025

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Pelee Island packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
President Hotel
3.5-star property

President Hotel

8.4/10 Very Good! (1,775 reviews)

Apr 12 - Apr 16

4 night stay

Chicago (ORD) to Miami (MIA)

United • PremiumEconomy

Miami (MIA) to Chicago (ORD)

Delta • PremiumEconomy
Price was $1,270, price is now $871 per person
$871
per person
found 1 day ago
I'd give 5 star for the staff. They were working with what they had doing the best that they could do with broken computers, walkie talkies that didn't work, elevators that where not function properly. Staff worked very hard with one computer to check in a long line of people, and worked very hard to feed a big crowd of guests every morning. I just watched. I had no desire to stand in that line. Again, very quality staff, but clearly the owners are investing zero money into maintaining even the basic things for this property. Bad business to do it that way. Of course they'll respond here and say that they "strive to maintain excellent facilities for their customers" but really, the owners aren't doing anything to maintain even the basic things.

Reviewed on Feb 20, 2026

Cavalier Hotel South Beach
3.5-star property

Cavalier Hotel South Beach

8.4/10 Very Good! (1,001 reviews)

Apr 12 - Apr 16

4 night stay

Chicago (ORD) to Miami (MIA)

United • PremiumEconomy

Miami (MIA) to Chicago (ORD)

Delta • PremiumEconomy
Save 100% on your flight
Price was $1,493, price is now $955 per person
$955
per person
found 1 day ago
Staff was great, elevator is tired, but I loved the proximity to everything

Reviewed on Jan 3, 2026

Hotel Riu Plaza Miami Beach
4.0-star property

Hotel Riu Plaza Miami Beach

8/10 Very Good! (1,120 reviews)

Apr 12 - Apr 16

4 night stay

Chicago (ORD) to Miami (MIA)

United • PremiumEconomy

Miami (MIA) to Chicago (ORD)

Delta • PremiumEconomy
Save 100% on your flight
Price was $1,829, price is now $1,204 per person
$1,204
per person
found 1 day ago
The hotel is clean. The staff will greet you but not immediately. The rooms are ok but the beds are small and everything is built for shorter stature people. I am average and the beds and toilet are short! TV's are older. Everything is average and ok.

Reviewed on Jan 19, 2026

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Pelee Island first class flight packages

Price found within the past 48 hours. Click for updated prices.
President Hotel
3.5-star property

President Hotel

8.4/10 Very Good! (1,775 reviews)

Apr 7 - Apr 14

7 night stay

Chicago (ORD) to Miami (MIA)

United • FirstClass

Miami (MIA) to Chicago (ORD)

Delta • FirstClass
Price was $2,060, price is now $1,350 per person
$1,350
per person
found 17 hours ago
I'd give 5 star for the staff. They were working with what they had doing the best that they could do with broken computers, walkie talkies that didn't work, elevators that where not function properly. Staff worked very hard with one computer to check in a long line of people, and worked very hard to feed a big crowd of guests every morning. I just watched. I had no desire to stand in that line. Again, very quality staff, but clearly the owners are investing zero money into maintaining even the basic things for this property. Bad business to do it that way. Of course they'll respond here and say that they "strive to maintain excellent facilities for their customers" but really, the owners aren't doing anything to maintain even the basic things.

Reviewed on Feb 20, 2026

The Retreat Collection at 1 Hotel & Homes South Beach
5.0-star property

The Retreat Collection at 1 Hotel & Homes South Beach

8/10 Very Good! (1 review)

Apr 7 - Apr 14

7 night stay

Chicago (ORD) to Miami (MIA)

United • FirstClass

Miami (MIA) to Chicago (ORD)

Delta • FirstClass
Price was $27,465, price is now $14,988 per person
$14,988
per person
found 17 hours ago
1 Hotel South Beach
5.0-star property

1 Hotel South Beach

9.4/10 Exceptional! (1,365 reviews)

Apr 7 - Apr 14

7 night stay

Chicago (ORD) to Miami (MIA)

United • FirstClass

Miami (MIA) to Chicago (ORD)

Delta • FirstClass
Price was $6,974, price is now $4,479 per person
$4,479
per person
found 17 hours ago
The best hotel I have ever stayed in!

Reviewed on Jan 17, 2026

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More About Flying To Pelee Island from Chicago

Route Information for Flights from Chicago to Pelee Island

Origin Airport IATA Code
CHI
Destination Airport IATA Code
null
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Pelee Island

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.