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Sun, May 31 - Wed, Jun 17
ORD
O'Hare Intl.
BOS
Logan Intl.
$236 Roundtrip, found 8 hours ago
$236
Roundtrip
found 8 hours ago
Select Delta flight, departing Sun, May 31 from O'Hare Intl. to Logan Intl., returning Wed, Jun 17, priced at $236 found 8 hours ago
Sat, May 30 - Tue, Jun 2
MDW
Midway Intl.
BOS
Logan Intl.
$262 Roundtrip, found 15 hours ago
$262
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Sat, May 30 from Midway Intl. to Logan Intl., returning Tue, Jun 2, priced at $262 found 15 hours ago
Sun, Jun 7 - Wed, Jun 10
MDW
Chicago
BOS
Boston
$192 Roundtrip, found 3 days ago
$192
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sun, Jun 7 from Chicago to Boston, returning Wed, Jun 10, priced at $192 found 3 days ago
Tue, Jun 30 - Sat, Jul 4
ORD
Chicago
BOS
Boston
$197 Roundtrip, found 19 hours ago
$197
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Tue, Jun 30 from Chicago to Boston, returning Sat, Jul 4, priced at $197 found 19 hours ago
Wed, Sep 2 - Sun, Sep 6
RFD
Rockford
BOS
Boston
$200 Roundtrip, found 6 days ago
$200
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Sep 2 from Rockford to Boston, returning Sun, Sep 6, priced at $200 found 6 days ago
Wed, Jun 10 - Sat, Jun 13
ORD
Chicago
BOS
Boston
$201 Roundtrip, found 4 hours ago
$201
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Wed, Jun 10 from Chicago to Boston, returning Sat, Jun 13, priced at $201 found 4 hours ago
Mon, Jun 8 - Mon, Jun 15
ORD
Chicago
ORH
Worcester
$226 Roundtrip, found 2 days ago
$226
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Jun 8 from Chicago to Worcester, returning Mon, Jun 15, priced at $226 found 2 days ago
Price found within the past 48 hours. Click for updated prices.
Meco Hotel - Hostel
2.0-star property

Meco Hotel - Hostel

8.6/10 Excellent! (422 reviews)

Jul 19 - Jul 21

2 night stay

Chicago (CHI) to Boston (BOS)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,040, price is now $565 per person
$565
per person
found 1 day ago
The staff member was super nice.

Reviewed on Nov 10, 2025

The Bell Inn
5.0-star property

The Bell Inn

9.4/10 Exceptional! (234 reviews)

Jul 19 - Jul 25

6 night stay

Chicago (CHI) to Boston (BOS)

Delta • Coach

Boston (BOS) to Chicago (CHI)

American Airlines • Coach
Price was $1,735, price is now $1,154 per person
$1,154
per person
found 1 day ago
Beautiful property. Had fun at the speak easy in the basement and the brunch was delicious.

Reviewed on Sep 21, 2025

Hotel Ivy Boston Common
2.5-star property

Hotel Ivy Boston Common

8.4/10 Very Good! (1,451 reviews)

Jun 29 - Jul 2

3 night stay

Chicago (CHI) to Boston (BOS)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $894, price is now $611 per person
$611
per person
found 1 day ago
Very convenient place to stay

Reviewed on Aug 18, 2025

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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.