Cheap flights from Milwaukee (MKE) to Pittsfield (ALB)

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Lowest round trip fares by airline from Milwaukee and Pittsfield

Cheapest prices ($168 One Way, $351 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in Pittsfield

Berkshire Inn

Berkshire Inn

2 out of 5
150 W Housatonic St, Pittsfield, MA
The price is $87 per night from Nov 24 to Nov 25
$87
includes taxes & fees
$77 per night
Nov 24 - Nov 25
Stay at this motel in Pittsfield. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.6/10 Good! (745 reviews)
"Nice area"

Reviewed on Nov 19, 2024

Berkshire Inn
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
The price is $101 per night from Dec 1 to Dec 2
$101
includes taxes & fees
$90 per night
Dec 1 - Dec 2
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,001 reviews)
"Room was clean, comfortable, and convenient. Dog Friendly! Will stay again!"

Reviewed on Nov 11, 2024

Best Western Plus Berkshire Hills Inn & Suites
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St., Pittsfield, MA
Stay at this 4-star guesthouse in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Colonial Theater and Berkshire Museum ...
8.8/10 Excellent! (267 reviews)
"I loved all the amenities and space provided in the suite. And it was very affordable. It was like staying in an apartment. It was very clean. The bedroom wall was thin though because I could hear snoring on the other side. Pretty view of the trees in the backyard."

Reviewed on Oct 26, 2024

The Central Downtown Inn & Suites
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Fly From Milwaukee to Pittsfield

Origin
Milwaukee
Destination
Pittsfield
Number of Daily Flights
Earliest Flight Departure Date
Latest Flight Departure Date
Popular Airlines

Cheap flights from Milwaukee to Pittsfield

Are you ready to book your flight, but feeling nervous about paying too much if prices drop in a few days? Don't play the waiting game. Our Best Price Guarantee means if you see a better fare for the same flight, we'll give you the difference in CheapCash, plus $50 more in CheapCash, which you can use to save on your hotel reservation.

If you have a frequent flier account, add it to your reservation to earn miles. And don't worry about getting stuck in a middle seat. Choose your seats when you book, so you'll be right where you want to be on departure day.

Save Even More Time and Money With a Pittsfield Travel Package

Once your flights are booked, why start all over again searching for a cheap hotel? Book your flight and hotel together, and save yourself more than time and energy. You'll also be able to take advantage of discounts and coupons on your Pittsfield vacation that you can't get when you book flights and hotel separately.

Relax in Pittsfield With Confidence and Convenience

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.