$63 Cheap flight deals from Chicago (CHI) to Eastham (PVC)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

This Weekend's Flight Deals from Chicago to Eastham

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, Jun 21 - Mon, Jun 23
MDW
Midway Intl.
BOS
Logan Intl.
$317 Roundtrip, found 5 days ago
$317
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Jun 21 from Midway Intl. to Logan Intl., returning Mon, Jun 23, priced at $317 found 5 days ago
Sat, Jun 21 - Mon, Jun 23
ORD
O'Hare Intl.
BOS
Logan Intl.
$358 Roundtrip, found 1 hour ago
$358
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, Jun 21 from O'Hare Intl. to Logan Intl., returning Mon, Jun 23, priced at $358 found 1 hour ago
Sat, Jun 21 - Sat, Jun 28
ORD
O'Hare Intl.
HYA
Barnstable Municipal
$664 Roundtrip, found 5 days ago
$664
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sat, Jun 21 from O'Hare Intl. to Barnstable Municipal, returning Sat, Jun 28, priced at $664 found 5 days ago

Airfares from $63 One Way, $125 Round Trip from Chicago to Eastham

Prices starting at $125 for return flights and $63 for one-way flights to Eastham were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Aug 24 - Thu, Aug 28
MDW
Chicago
BOS
Boston
$125 Roundtrip, found 3 days ago
$125
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sun, Aug 24 from Chicago to Boston, returning Thu, Aug 28, priced at $125 found 3 days ago
Thu, Dec 4 - Sun, Dec 7
ORD
Chicago
BOS
Boston
$137 Roundtrip, found 3 hours ago
$137
Roundtrip
found 3 hours ago
Select Delta flight, departing Thu, Dec 4 from Chicago to Boston, returning Sun, Dec 7, priced at $137 found 3 hours ago
Thu, Dec 4 - Sun, Dec 7
ORD
Chicago
BOS
Boston
$137 Roundtrip, found 3 hours ago
$137
Roundtrip
found 3 hours ago
Select United flight, departing Thu, Dec 4 from Chicago to Boston, returning Sun, Dec 7, priced at $137 found 3 hours ago
Thu, Dec 4 - Sat, Dec 6
ORD
Chicago
BOS
Boston
$137 Roundtrip, found 3 hours ago
$137
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Thu, Dec 4 from Chicago to Boston, returning Sat, Dec 6, priced at $137 found 3 hours ago
Fri, Jun 27 - Mon, Jun 30
MDW
Chicago
BOS
Boston
$210 Roundtrip, found 14 hours ago
$210
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Fri, Jun 27 from Chicago to Boston, returning Mon, Jun 30, priced at $210 found 14 hours ago

Eastham economy flight packages

Price found within the past 48 hours. Click for updated prices.
D. Hotel Suites & Spa
3.0-star property

D. Hotel Suites & Spa

9.4/10 Exceptional! (2,269 reviews)

Aug 14 - Aug 18

4 night stay

Chicago (MDW) to Boston (BOS)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 2 hours ago
The spacious rooms, the indoor pool, hot tub and of course the staff was amazing, especially Jim, he made a disabled young mans Birthday extra special with a simple touch. First time and will be returning soon.

Reviewed on Oct 6, 2024

DoubleTree Suites by Hilton Hotel Boston - Cambridge
4.0-star property

DoubleTree Suites by Hilton Hotel Boston - Cambridge

8.8/10 Excellent! (1,002 reviews)

Jul 22 - Jul 27

5 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Coach

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Coach
Save 100% on your flight
per person
found 14 hours ago
My stay was very comfortable but there was a few things that I was unsatisfied with. So I travel alot for work and never have I ever had to pay $50 a night for parking, that was a little insane to me. Also I had requested a room with a tub and I got one with a shower and ontop of that, every time I went to take a shower, there were some kind of knats or fruit flys coming out of the drain so that was definitely an ick. And lastly for a hotel that charges a lot of money to stay there, there should not be rammy teenage boys running around the hotel floors all hours of the day and night and slamming doors. I had to put on my white noise machine just to drown them out so I could sleep. But other than that it was fine.

Reviewed on Feb 6, 2025

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,007 reviews)

Aug 3 - Aug 10

7 night stay

Chicago (CHI) to Boston (BOS)

Southwest Airlines • Coach

Boston (BOS) to Chicago (CHI)

Spirit Airlines • Coach
Save 100% on your flight
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

Don't see what you're looking for?
See all available trips from Chicago to Eastham
View all trips

Eastham first class flight packages

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

Encore Boston Harbor

9.6/10 Exceptional! (2,977 reviews)

Jul 26 - Jul 29

3 night stay

Chicago (CHI) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
per person
found 1 day ago
No microwave at all!!

Reviewed on May 18, 2025

The Langham, Boston
5.0-star property

The Langham, Boston

9.6/10 Exceptional! (1,000 reviews)

Jul 26 - Jul 29

3 night stay

Chicago (CHI) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
per person
found 1 day ago
Clean lovely staff quiet well kept

Reviewed on May 11, 2025

The Whitney Hotel
4.0-star property

The Whitney Hotel

9.6/10 Exceptional! (407 reviews)

Jul 26 - Jul 29

3 night stay

Chicago (CHI) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
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

Don't see what you're looking for?
See all available trips from Chicago to Eastham
View all trips

More About Flying To Eastham from Chicago

Route Information for Flights from Chicago to Eastham

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

Chicago to Eastham

Great Deals on Flights From Chicago to Eastham

Spend more of your time and money at Eastham instead of sitting at your computer, searching for discount Chicago to Eastham flights. This is why Orbitz makes it easy for you to check out destinations, plan your trip, and book your air fare, hotel, car rental, and more in just one place. Our low price guarantee means that you get great deals on flights from Chicago to Eastham.

Flights That Fit Your Budget

Traveling on a budget? Not to worry if you are using Orbitz. We monitor thousands of fares to make sure we show you the best air ticket prices available for your travel dates. Besides amazing prices on Chicago to Eastham flights, we offer you great deals on hotels, vacation packages, and last-minute getaways for the perfect trip.

Orbitz customers can receive credit for frequent flyer miles and points. Simply provide your frequent flyer details when you book qualifying Chicago to Eastham flights with Orbitz.

Search for Flights from Chicago to Eastham on the Go

Orbitz offers free mobile apps for iPad, iPhone, and Android-based devices, so even the busiest trip-planner can research and book flights from Chicago to Eastham. Find cheap Chicago to Eastham flights, research local festivities and attractions, and book reservations while sitting in the salon. Orbitz will also update you on flight delays with free alerts sent to your mobile phone or email address, so you’re never left in the dark.

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.