$53 Cheap flight deals from Chicago (CHI) to Newton (BOS)

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This Weekend's Flight Deals from Chicago to Newton

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.

Sat, Jan 10 - Wed, Jan 14
ORD
O'Hare Intl.
BOS
Logan Intl.
$234 Roundtrip, found 12 hours ago
$234
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Sat, Jan 10 from O'Hare Intl. to Logan Intl., returning Wed, Jan 14, priced at $234 found 12 hours ago
Sun, Jan 11 - Mon, Jan 12
MDW
Midway Intl.
BOS
Logan Intl.
$269 Roundtrip, found 1 day ago
$269
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sun, Jan 11 from Midway Intl. to Logan Intl., returning Mon, Jan 12, priced at $269 found 1 day ago

Airfares from $53 One Way, $104 Round Trip from Chicago to Newton

Prices starting at $104 for return flights and $53 for one-way flights to Newton 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, Feb 17 - Wed, Feb 18
MDW
Chicago
BOS
Boston
$104 Roundtrip, found 3 days ago
$104
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Feb 17 from Chicago to Boston, returning Wed, Feb 18, priced at $104 found 3 days ago
Wed, Mar 25 - Mon, Mar 30
ORD
Chicago
BOS
Boston
$105 Roundtrip, found 13 hours ago
$105
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Wed, Mar 25 from Chicago to Boston, returning Mon, Mar 30, priced at $105 found 13 hours ago
Sat, Feb 7 - Wed, Feb 18
ORD
Chicago
BOS
Boston
$107 Roundtrip, found 1 day ago
$107
Roundtrip
found 1 day ago
Select United flight, departing Sat, Feb 7 from Chicago to Boston, returning Wed, Feb 18, priced at $107 found 1 day ago
Mon, Feb 2 - Tue, Feb 3
ORD
Chicago
BOS
Boston
$108 Roundtrip, found 2 hours ago
$108
Roundtrip
found 2 hours ago
Select Delta flight, departing Mon, Feb 2 from Chicago to Boston, returning Tue, Feb 3, priced at $108 found 2 hours ago
Thu, Jan 15 - Sat, Jan 17
ORD
Chicago
BOS
Boston
$112 Roundtrip, found 1 day ago
$112
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Jan 15 from Chicago to Boston, returning Sat, Jan 17, priced at $112 found 1 day ago

Newton economy flight packages

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

Boston Harbor Hotel

9.8/10 Exceptional! (1,005 reviews)

Feb 9 - Feb 11

2 night stay

Chicago (CHI) to Boston (BOS)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $870, price is now $534 per person
$534
per person
found 16 hours 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 Charles Hotel
4.0-star property

The Charles Hotel

9.4/10 Exceptional! (1,003 reviews)

Feb 7 - Feb 14

7 night stay

Chicago (CHI) to Boston (BOS)

Delta • Roundtrip • Coach
Price was $1,987, price is now $1,032 per person
$1,032
per person
found 22 hours 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

The Newbury Boston
5.0-star property

The Newbury Boston

9.4/10 Exceptional! (536 reviews)

Feb 7 - Feb 14

7 night stay

Chicago (CHI) to Boston (BOS)

Delta • Roundtrip • Coach
Save 100% on your flight
Price was $2,023, price is now $1,211 per person
$1,211
per person
found 22 hours ago
First time staying at the Newbury. What a pleasant experience😊 starting from the warm welcome from the bellman to the front desk staff Mario. He was so informative and thoughtful. Definitely will return to stay here again 👍

Reviewed on Jul 3, 2023

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Newton packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Hotel & Suites Swansea by IHG
3.5-star property

Holiday Inn Express Hotel & Suites Swansea by IHG

7.8/10 Good! (1,001 reviews)

Feb 20 - Feb 23

3 night stay

Chicago (ORD) to Boston (BOS)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $623, price is now $540 per person
$540
per person
just found
Hotel was mostly fine. Could hear lots of noise outside the room through the door and walls. Was very expensive for the level of quality but it was a holiday weekend.

Reviewed on May 28, 2025

Red Roof Inn & Suites Swansea
2.0-star property

Red Roof Inn & Suites Swansea

6.8/10 (187 reviews)

Feb 20 - Feb 23

3 night stay

Chicago (ORD) to Boston (BOS)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $585, price is now $585 per person
$585
per person
just found
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 Newton from Chicago

Route Information for Flights from Chicago to Newton

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

Chicago to Newton

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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.