$49 Cheap flight deals from Chicago (CHI) to Stoneham (BOS)

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This Weekend's Flight Deals from Chicago to Stoneham

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.

Fri, Jan 30 - Sat, Jan 31
ORD
O'Hare Intl.
BOS
Logan Intl.
$138 Roundtrip, found 1 hour ago
$138
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Fri, Jan 30 from O'Hare Intl. to Logan Intl., returning Sat, Jan 31, priced at $138 found 1 hour ago
Fri, Jan 30 - Sun, Feb 1
MDW
Midway Intl.
BOS
Logan Intl.
$138 Roundtrip, found 2 days ago
$138
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Jan 30 from Midway Intl. to Logan Intl., returning Sun, Feb 1, priced at $138 found 2 days ago
Fri, Jan 30 - Sat, Jan 31
RFD
Greater Rockford
BOS
Logan Intl.
$142 Roundtrip, found 2 days ago
$142
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Jan 30 from Greater Rockford to Logan Intl., returning Sat, Jan 31, priced at $142 found 2 days ago

Airfares from $49 One Way, $97 Round Trip from Chicago to Stoneham

Prices starting at $97 for return flights and $49 for one-way flights to Stoneham were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Mar 4 - Sat, Mar 7
ORD
Chicago
BOS
Boston
$97 Roundtrip, found 1 day ago
$97
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Mar 4 from Chicago to Boston, returning Sat, Mar 7, priced at $97 found 1 day ago
Wed, Mar 4 - Sun, Mar 8
ORD
Chicago
BOS
Boston
$97 Roundtrip, found 1 day ago
$97
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Mar 4 from Chicago to Boston, returning Sun, Mar 8, priced at $97 found 1 day ago
Wed, Feb 25 - Sun, Mar 1
ORD
Chicago
BOS
Boston
$98 Roundtrip, found 18 hours ago
$98
Roundtrip
found 18 hours ago
Select JetBlue Airways flight, departing Wed, Feb 25 from Chicago to Boston, returning Sun, Mar 1, priced at $98 found 18 hours ago
Sat, Mar 7 - Wed, Mar 11
ORD
Chicago
BOS
Boston
$105 Roundtrip, found 2 days ago
$105
Roundtrip
found 2 days ago
Select United flight, departing Sat, Mar 7 from Chicago to Boston, returning Wed, Mar 11, priced at $105 found 2 days ago
Sat, Feb 14 - Wed, Feb 18
MDW
Chicago
BOS
Boston
$128 Roundtrip, found 11 hours ago
$128
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Sat, Feb 14 from Chicago to Boston, returning Wed, Feb 18, priced at $128 found 11 hours ago

Stoneham economy flight packages

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

The Boston Hotel

7.4/10 Good! (802 reviews)

Mar 18 - Mar 23

5 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $683, price is now $513 per person
$513
per person
found 1 day ago
We appreciated the spacious rooms, the friendly and responsive staff, and how clean the rooms and linens were. We had the King Suite, and it fit us and our kids well. The rooms had windows an it was a comfortable space. One thing to know is that it is an older building and the hot water takes longer than you anticipate to get to the room. Be patient, it will come. We like that it is an independent establishment and the staff seem to communicate well with each other, and were definitely responsive when we had questions. For the price, we think this a very pleasant and welcoming place to stay.

Reviewed on Nov 29, 2025

The Charles Hotel
4.0-star property

The Charles Hotel

9.4/10 Exceptional! (1,003 reviews)

Mar 18 - Mar 23

5 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,469, price is now $976 per person
$976
per person
found 1 day ago
Great Cambridge hotel. Close to T stop and great location in Harvard Square. Lobby is a great place to read or get some work done. Rooms very comfortable.

Reviewed on Mar 31, 2025

Encore Boston Harbor
5.0-star property

Encore Boston Harbor

9.6/10 Exceptional! (3,386 reviews)

Mar 6 - Mar 11

5 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,528, price is now $1,140 per person
$1,140
per person
found 1 day ago
Excellent experience

Reviewed on Jan 12, 2026

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Stoneham first class flight packages

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

The Charles Hotel

9.4/10 Exceptional! (1,003 reviews)

Mar 6 - Mar 8

2 night stay

Chicago (ORD) to Boston (BOS)

United • Roundtrip • FirstClass
Price was $930, price is now $748 per person
$748
per person
found 1 day ago
Great Cambridge hotel. Close to T stop and great location in Harvard Square. Lobby is a great place to read or get some work done. Rooms very comfortable.

Reviewed on Mar 31, 2025

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,005 reviews)

Mar 6 - Mar 8

2 night stay

Chicago (ORD) to Boston (BOS)

United • Roundtrip • FirstClass
Price was $1,257, price is now $900 per person
$900
per person
found 1 day ago
The staff is VERY attentive to all your needs. It just makes everything easy and more comfortable: room service to concierge to valet parking etc. etc.

Reviewed on Mar 24, 2024

The Whitney Hotel
4.0-star property

The Whitney Hotel

9.6/10 Exceptional! (482 reviews)

Mar 6 - Mar 8

2 night stay

Chicago (ORD) to Boston (BOS)

United • Roundtrip • FirstClass
Price was $946, price is now $780 per person
$780
per person
found 1 day ago
What a gem in Boston! I've been to Boston many times and usually stay closer to the Downtown Crossing area. This time we stayed at the Whitney, choosing to try out that part of town. We loved it! Bigger than a boutique hotel, but small enough to feel intimate. Charles St is a great walking street, and we loved the location. The room was on the ground level (actually partly below ground) but was excellent! Well-appointed room, a good amount of space for Boston, and super professional staff. I'll be back when I come back to Boston

Reviewed on Jul 30, 2024

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More About Flying To Stoneham from Chicago

Route Information for Flights from Chicago to Stoneham

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

Chicago to Stoneham

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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.