$83 Cheap flight deals from Chicago (CHI) to Rye (BOS)

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This Weekend's Flight Deals from Chicago to Rye

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.

Sun, Aug 16 - Fri, Aug 21
ORD
O'Hare Intl.
BOS
Logan Intl.
$284 Roundtrip, found 2 hours ago
$284
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Sun, Aug 16 from O'Hare Intl. to Logan Intl., returning Fri, Aug 21, priced at $284 found 2 hours ago
Sat, Aug 15 - Sat, Aug 22
MDW
Midway Intl.
BOS
Logan Intl.
$290 Roundtrip, found 4 days ago
$290
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Sat, Aug 15 from Midway Intl. to Logan Intl., returning Sat, Aug 22, priced at $290 found 4 days ago
Fri, Aug 14 - Tue, Aug 18
RFD
Greater Rockford
BOS
Logan Intl.
$366 Roundtrip, found 4 days ago
$366
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Aug 14 from Greater Rockford to Logan Intl., returning Tue, Aug 18, priced at $366 found 4 days ago
Sun, Aug 16 - Mon, Aug 17
MDW
Midway Intl.
MHT
Manchester-Boston Regional
$633 Roundtrip, found 20 hours ago
$633
Roundtrip
found 20 hours ago
Select Southwest Airlines flight, departing Sun, Aug 16 from Midway Intl. to Manchester-Boston Regional, returning Mon, Aug 17, priced at $633 found 20 hours ago

Airfares from $83 One Way, $156 Round Trip from Chicago to Rye

Prices starting at $156 for return flights and $83 for one-way flights to Rye were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Nov 10 - Tue, Nov 17
ORD
Chicago
BOS
Boston
$156 Roundtrip, found 3 hours ago
$156
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Tue, Nov 10 from Chicago to Boston, returning Tue, Nov 17, priced at $156 found 3 hours ago
Sat, Sep 5 - Thu, Sep 10
ORD
Chicago
BOS
Boston
$159 Roundtrip, found 20 hours ago
$159
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Sat, Sep 5 from Chicago to Boston, returning Thu, Sep 10, priced at $159 found 20 hours ago
Tue, Nov 10 - Tue, Nov 17
ORD
Chicago
BOS
Boston
$165 Roundtrip, found 3 hours ago
$165
Roundtrip
found 3 hours ago
Select Delta flight, departing Tue, Nov 10 from Chicago to Boston, returning Tue, Nov 17, priced at $165 found 3 hours ago
Tue, Nov 10 - Tue, Nov 17
ORD
Chicago
BOS
Boston
$165 Roundtrip, found 3 hours ago
$165
Roundtrip
found 3 hours ago
Select United flight, departing Tue, Nov 10 from Chicago to Boston, returning Tue, Nov 17, priced at $165 found 3 hours ago
Wed, Oct 21 - Mon, Oct 26
ORD
Chicago
BOS
Boston
$165 Roundtrip, just found
$165
Roundtrip
just found
Select JetBlue Airways flight, departing Wed, Oct 21 from Chicago to Boston, returning Mon, Oct 26, priced at $165 just found

Rye economy flight packages

Price found within the past 48 hours. Click for updated prices.
Good Hotels Boston
2.0-star property

Good Hotels Boston

8/10 Very Good! (55 reviews)

Sep 24 - Sep 27

3 night stay

Chicago (CHI) to Boston (BOS)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,942, price is now $1,246 per person
$1,246
per person
found 1 hour ago
Very nice people and had excellent help!

Reviewed on Aug 7, 2026

The Charles Hotel
5.0-star property

The Charles Hotel

9.4/10 Exceptional! (1,006 reviews)

Sep 24 - Sep 29

5 night stay

Chicago (CHI) to Boston (BOS)

JetBlue Airways • Coach

Boston (BOS) to Chicago (CHI)

Southwest Airlines • Coach
Save 100% on your flight
Price was $2,624, price is now $1,716 per person
$1,716
per person
found 1 day ago

Raffles Boston
5.0-star property

Raffles Boston

9.6/10 Exceptional! (285 reviews)

Sep 24 - Sep 29

5 night stay

Chicago (CHI) to Boston (BOS)

JetBlue Airways • Coach

Boston (BOS) to Chicago (CHI)

Southwest Airlines • Coach
Save 100% on your flight
Price was $4,183, price is now $3,029 per person
$3,029
per person
found 1 day ago

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Rye packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Iris Hotel Boston
4.0-star property

Iris Hotel Boston

9.4/10 Exceptional! (612 reviews)

Sep 13 - Sep 20

7 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,112, price is now $1,540 per person
$1,540
per person
found 1 day ago
The stay at the Iris Hotel Boston was perfect! The staff went above and beyond to accommodate, make comfortable, welcome us. The bartender was outstanding! The room was beautiful with every need anticipated. Convenient and fun neighborhood with many restaurant, cuisine, shopping and transportation options. I will certainly be back!

Reviewed on Aug 11, 2026

The Whitney Hotel
4.0-star property

The Whitney Hotel

9.6/10 Exceptional! (600 reviews)

Sep 13 - Sep 20

7 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $4,009, price is now $3,031 per person
$3,031
per person
found 1 day ago
The location is very convenient, staff was polite and friendly, room was very comfortable.

Reviewed on Aug 8, 2026

The Atlas Hotel
4.5-star property

The Atlas Hotel

9.4/10 Exceptional! (254 reviews)

Sep 16 - Sep 23

7 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,538, price is now $1,983 per person
$1,983
per person
found 1 day ago
The hotel was clean and well maintained. Very innovative designed. The staff was constantly hospitable - opening every door when we enter. The only downside was the room next to us was very loud on our last night which kept us up most of the night - nothing to do with the hotel. I didn’t complain and am hoping for some compensation back.

Reviewed on Aug 10, 2026

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Rye first class flight packages

Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston
4.5-star property

Fairmont Copley Plaza, Boston

9/10 Wonderful! (1,298 reviews)

Sep 11 - Sep 13

2 night stay

Chicago (CHI) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Price was $1,146, price is now $897 per person
$897
per person
found 5 hours ago
Give Cory love. She’s such a sweetie

Reviewed on Aug 11, 2026

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,006 reviews)

Sep 11 - Sep 13

2 night stay

Chicago (CHI) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Price was $1,777, price is now $1,362 per person
$1,362
per person
found 5 hours ago

Raffles Boston
5.0-star property

Raffles Boston

9.6/10 Exceptional! (285 reviews)

Sep 11 - Sep 13

2 night stay

Chicago (CHI) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Price was $1,957, price is now $1,565 per person
$1,565
per person
found 5 hours ago

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More About Flying To Rye from Chicago

Route Information for Flights from Chicago to Rye

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

Chicago to Rye

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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.