$82 Cheap flight deals from Chicago (CHI) to San Juan Island (SEA)

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This Weekend's Flight Deals from Chicago to San Juan Island

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Feb 7 - Mon, Feb 9
ORD
O'Hare Intl.
SEA
Seattle - Tacoma Intl.
$321 Roundtrip, found 2 hours ago
$321
Roundtrip
found 2 hours ago
Select Bargain Flight flight, departing Sat, Feb 7 from O'Hare Intl. to Seattle - Tacoma Intl., returning Mon, Feb 9, priced at $321 found 2 hours ago
Sat, Feb 7 - Tue, Feb 10
RFD
Greater Rockford
SEA
Seattle - Tacoma Intl.
$366 Roundtrip, found 4 days ago
$366
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Feb 7 from Greater Rockford to Seattle - Tacoma Intl., returning Tue, Feb 10, priced at $366 found 4 days ago
Sat, Feb 7 - Tue, Feb 10
MDW
Midway Intl.
SEA
Seattle - Tacoma Intl.
$367 Roundtrip, found 4 days ago
$367
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Sat, Feb 7 from Midway Intl. to Seattle - Tacoma Intl., returning Tue, Feb 10, priced at $367 found 4 days ago
Sun, Feb 8 - Sat, Feb 14
ORD
O'Hare Intl.
BLI
Bellingham Intl.
$576 Roundtrip, found 1 day ago
$576
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Sun, Feb 8 from O'Hare Intl. to Bellingham Intl., returning Sat, Feb 14, priced at $576 found 1 day ago

Airfares from $82 One Way, $166 Round Trip from Chicago to San Juan Island

Prices starting at $166 for return flights and $82 for one-way flights to San Juan 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.

Thu, Mar 5 - Sat, Mar 7
MDW
Chicago
SEA
Seattle
$166 Roundtrip, found 6 days ago
$166
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Mar 5 from Chicago to Seattle, returning Sat, Mar 7, priced at $166 found 6 days ago
Wed, Mar 11 - Sat, Mar 14
ORD
Chicago
SEA
Seattle
$177 Roundtrip, found 5 days ago
$177
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Mar 11 from Chicago to Seattle, returning Sat, Mar 14, priced at $177 found 5 days ago
Wed, Apr 1 - Thu, Apr 9
ORD
Chicago
SEA
Seattle
$177 Roundtrip, found 5 days ago
$177
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Apr 1 from Chicago to Seattle, returning Thu, Apr 9, priced at $177 found 5 days ago
Thu, Mar 5 - Sat, Mar 7
RFD
Rockford
SEA
Seattle
$181 Roundtrip, found 6 days ago
$181
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, Mar 5 from Rockford to Seattle, returning Sat, Mar 7, priced at $181 found 6 days ago
Sat, Feb 28 - Tue, Mar 3
ORD
Chicago
SEA
Seattle
$184 Roundtrip, found 19 hours ago
$184
Roundtrip
found 19 hours ago
Select United flight, departing Sat, Feb 28 from Chicago to Seattle, returning Tue, Mar 3, priced at $184 found 19 hours ago

San Juan Island economy flight packages

Price found within the past 48 hours. Click for updated prices.
Graduate by Hilton Seattle
4.0-star property

Graduate by Hilton Seattle

8.2/10 Very Good! (1,002 reviews)

Mar 26 - Mar 30

4 night stay

Chicago (CHI) to Seattle (SEA)

Southwest Airlines • Coach

Seattle (SEA) to Chicago (CHI)

Delta • Coach
Price was $728, price is now $554 per person
$554
per person
found 22 hours ago
The Graduate is a cool, stylish choice. It is mostly aimed at a younger crowd (we are in our 40's and were there with our daughter), but we all found it comfortable. The rooftop bar, the Mountaineering Club, is a great place for panoramic views of Seattle. The U District is as central a location as you will find, but be aware that there will be noise on the street at night if you keep your windows open. The Poindexter Cafe downstairs was a great place to grab bagels and coffee in the morning, and street parking for the night was easy to find in the neighborhood.

Reviewed on Aug 6, 2025

1 Hotel Seattle
5.0-star property

1 Hotel Seattle

9.2/10 Wonderful! (165 reviews)

Mar 26 - Mar 30

4 night stay

Chicago (CHI) to Seattle (SEA)

Southwest Airlines • Coach

Seattle (SEA) to Chicago (CHI)

Delta • Coach
Save 100% on your flight
Price was $1,334, price is now $745 per person
$745
per person
found 22 hours ago
This was our third time staying at this particular hotel in the last 10 years so we have a history to compare it to. It will be the last time we stay here. For the room price and the options that you have to DEPEND on the hotel staff to provide for you in a timely manner, it wasn't worth it. Nice property to look at though

Reviewed on May 27, 2025

Hilton Bellevue
3.5-star property

Hilton Bellevue

8.4/10 Very Good! (1,003 reviews)

Mar 9 - Mar 12

3 night stay

Chicago (ORD) to Seattle (SEA)

Delta • Roundtrip • Coach
Price was $760, price is now $565 per person
$565
per person
found 1 day ago
The initial room was not great and staff was not helpful until a manager got involved.

Reviewed on Jul 11, 2025

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San Juan Island first class flight packages

Price found within the past 48 hours. Click for updated prices.
Sleep Inn - SeaTac Airport
2.5-star property

Sleep Inn - SeaTac Airport

8.4/10 Very Good! (2,134 reviews)

Mar 21 - Mar 29

8 night stay

Chicago (CHI) to Seattle (SEA)

American Airlines • FirstClass

Seattle (SEA) to Chicago (CHI)

Delta • FirstClass
Price was $1,238, price is now $940 per person
$940
per person
found 22 hours ago
Very nice large room, clean and comfortable. Nice hot breakfast with lots of choices

Reviewed on Oct 11, 2025

Mayflower Park Hotel
4.0-star property

Mayflower Park Hotel

9.4/10 Exceptional! (2,387 reviews)

Mar 21 - Mar 29

8 night stay

Chicago (CHI) to Seattle (SEA)

American Airlines • FirstClass

Seattle (SEA) to Chicago (CHI)

Delta • FirstClass
Price was $1,578, price is now $1,106 per person
$1,106
per person
found 22 hours ago
Very nice place... old fashioned and well kept

Reviewed on Nov 13, 2025

The Belltown Inn
2.5-star property

The Belltown Inn

9.2/10 Wonderful! (4,267 reviews)

Mar 21 - Mar 29

8 night stay

Chicago (CHI) to Seattle (SEA)

American Airlines • FirstClass

Seattle (SEA) to Chicago (CHI)

Delta • FirstClass
Price was $1,490, price is now $1,148 per person
$1,148
per person
found 22 hours ago
The room was clean and cozy. Staff was helpful and friendly. Walking distance to area attractions and dining. Rooftop terrace has an outstanding view. Will stay there again.

Reviewed on Nov 1, 2025

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More About Flying To San Juan Island from Chicago

Route Information for Flights from Chicago to San Juan Island

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

Chicago to San Juan 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.