Cheap flight deals from Chicago (CHI) to Kittery (BOS)

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Kittery economy flight packages

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

The Revolution Hotel

9/10 Wonderful! (2,173 reviews)

Dec 27 - Dec 30

3 night stay

Chicago (CHI) to Boston (BOS)

Southwest Airlines • Roundtrip • Coach
Price was $436, price is now $300 per person
$300
per person
found 3 hours ago
Very clean, staff friendly, amazing location

Reviewed on Oct 30, 2025

AC Hotel by Marriott Boston Downtown
3.5-star property

AC Hotel by Marriott Boston Downtown

8.8/10 Excellent! (1,008 reviews)

Dec 26 - Jan 2

7 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Non-stop • Coach

Boston (BOS) to Chicago (ORD)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $872, price is now $625 per person
$625
per person
found 1 day ago
It would bew so much better if the room had enough lighting. Breakfast very ordinary for quite a lot of money.

Reviewed on Sep 23, 2025

The Whitney Hotel
4.0-star property

The Whitney Hotel

9.6/10 Exceptional! (475 reviews)

Dec 28 - Dec 30

2 night stay

Chicago (CHI) to Boston (BOS)

United • Coach

Boston (BOS) to Chicago (CHI)

Southwest Airlines • Coach
Save 100% on your flight
Price was $599, price is now $433 per person
$433
per person
just found
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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Kittery packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Fall River North by IHG
2.5-star property

Holiday Inn Express Fall River North by IHG

8.2/10 Very Good! (1,015 reviews)

Dec 12 - Dec 14

2 night stay

Chicago (CHI) to Boston (BOS)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $631, price is now $600 per person
$600
per person
found 5 hours ago
Great place, great staff!

Reviewed on Oct 14, 2025

Fairfield Inn & Suites by Marriott Somerset
2.5-star property

Fairfield Inn & Suites by Marriott Somerset

9.4/10 Exceptional! (471 reviews)

Dec 12 - Dec 14

2 night stay

Chicago (CHI) to Boston (BOS)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $678, price is now $677 per person
$677
per person
found 5 hours ago
The room was very clean and the property was quiet. The staff was always friendly and helpful. The free breakfast had a variety of choices. Major freeways (195 and 95) are easily accessible within 5 minutes from the hotel. I plan to stay again-this is the best hotel in the are!

Reviewed on Jul 27, 2023

Red Roof Inn & Suites Swansea
2.0-star property

Red Roof Inn & Suites Swansea

6.8/10 (179 reviews)

Dec 12 - Dec 14

2 night stay

Chicago (CHI) to Boston (BOS)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $623, price is now $623 per person
$623
per person
found 5 hours ago
Was an OKAY stay. They say on the Orbitz app that rooms are kept open for a day before new people staying but that was a lie. Room had old scratch tickets laying around. Also, shower and all water didn't work. Turned shower on to get a few little streams of dark brown water that never stopped nor changed. So showering was not an option. Area is okay. But sketchy but if you know the area, you're okay. Highway is right outside the room so the view is so/so. The property says that the room was $110 but yet made me sign a paper saying that the rate was only $77. Maybe Orbitz needs to look into that? Would try again and hopefully these comments and concerns can be addressed in the near future

Reviewed on May 5, 2022

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More About Flying To Kittery from Chicago

Route Information for Flights from Chicago to Kittery

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

Chicago to Kittery

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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.

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