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MDW
Midway Intl.
BOS
Logan Intl.
$290 Roundtrip, found 3 days ago
$290
Roundtrip
found 3 days ago
ORD
O'Hare Intl.
BOS
Logan Intl.
$321 Roundtrip, found 6 hours ago
$321
Roundtrip
found 6 hours ago
RFD
Greater Rockford
BOS
Logan Intl.
$366 Roundtrip, found 3 days ago
$366
Roundtrip
found 3 days ago
ORD
O'Hare Intl.
MHT
Manchester-Boston Regional
$633 Roundtrip, found 1 day ago
$633
Roundtrip
found 1 day ago
MDW
Chicago
BOS
Boston
$166 Roundtrip, found 8 hours ago
$166
Roundtrip
found 8 hours ago
ORD
Chicago
BOS
Boston
$168 Roundtrip, just found
$168
Roundtrip
just found
ORD
Chicago
BOS
Boston
$168 Roundtrip, just found
$168
Roundtrip
just found
ORD
Chicago
BOS
Boston
$187 Roundtrip, just found
$187
Roundtrip
just found
ORD
Chicago
BOS
Boston
$189 Roundtrip, found 6 hours ago
$189
Roundtrip
found 6 hours ago
Price found within the past 48 hours. Click for updated prices.
2.0-star property
Good Hotels Boston
8/10 Very Good! (55 reviews)
Sep 25 - Sep 28
3 night stay
Chicago (CHI) to Boston (BOS)
JetBlue Airways • Coach
Boston (BOS) to Chicago (CHI)
Frontier Airlines • Coach
Price was $1,781, price is now $1,163 per person
$1,163
per person
found 1 day ago
Very nice people and had excellent help!
Reviewed on Aug 7, 2026
4.0-star property
The Godfrey Hotel Boston
9.6/10 Exceptional! (5,158 reviews)
Oct 2 - Oct 10
8 night stay
Chicago (CHI) to Boston (BOS)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $3,376, price is now $2,284 per person
$2,284
per person
found 1 day ago
The location of the hotel was great, the staff was friendly and helpful, you get a free basket of snacks that is replentished daily. Breakfast is not included but there is a coffee shop attached and two good breakfasat places right around the corner.
Reviewed on Aug 10, 2026
Price found within the past 48 hours. Click for updated prices.
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 3 hours ago
Very nice boutique with good amenities. Parking was easy,and close proximity to Fenway Park via MBTA .
One complaint was the puffed up pillows for sleeping. Very uncomfortable. Also heavy comforter on beds in the summer.
Next time would explore other hotels.
Reviewed on Aug 9, 2026
4.0-star property
The Whitney Hotel
9.6/10 Exceptional! (597 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 3 hours ago
The location is very convenient, staff was polite and friendly, room was very comfortable.
Reviewed on Aug 8, 2026
4.5-star property
The Atlas Hotel
9.4/10 Exceptional! (242 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 4 hours 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
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.