$52 Cheap flight deals from Chicago (CHI) to New Milford (HPN)

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This Weekend's Flight Deals from Chicago to New Milford

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.

Sun, Apr 12 - Thu, Apr 16
ORD
O'Hare Intl.
HVN
Tweed - New Haven Regional
$371 Roundtrip, found 7 hours ago
$371
Roundtrip
found 7 hours ago
Select Avelo Airlines flight, departing Sun, Apr 12 from O'Hare Intl. to Tweed - New Haven Regional, returning Thu, Apr 16, priced at $371 found 7 hours ago
Fri, Apr 10 - Sun, Apr 12
ORD
O'Hare Intl.
HPN
Westchester County
$534 Roundtrip, found 3 days ago
$534
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Apr 10 from O'Hare Intl. to Westchester County, returning Sun, Apr 12, priced at $534 found 3 days ago

Airfares from $52 One Way, $103 Round Trip from Chicago to New Milford

Prices starting at $103 for return flights and $52 for one-way flights to New Milford were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Sep 25 - Sun, Sep 27
ORD
Chicago
HVN
New Haven
$103 Roundtrip, found 1 hour ago
$103
Roundtrip
found 1 hour ago
Select Avelo Airlines flight, departing Fri, Sep 25 from Chicago to New Haven, returning Sun, Sep 27, priced at $103 found 1 hour ago
Thu, Jun 4 - Sun, Jun 7
ORD
Chicago
HVN
New Haven
$105 Roundtrip, found 7 hours ago
$105
Roundtrip
found 7 hours ago
Select Avelo Airlines flight, departing Thu, Jun 4 from Chicago to New Haven, returning Sun, Jun 7, priced at $105 found 7 hours ago
Fri, Apr 24 - Mon, Apr 27
ORD
Chicago
HVN
New Haven
$113 Roundtrip, found 13 hours ago
$113
Roundtrip
found 13 hours ago
Select Avelo Airlines flight, departing Fri, Apr 24 from Chicago to New Haven, returning Mon, Apr 27, priced at $113 found 13 hours ago
Fri, May 1 - Fri, May 8
ORD
Chicago
HVN
New Haven
$115 Roundtrip, found 5 days ago
$115
Roundtrip
found 5 days ago
Select Avelo Airlines flight, departing Fri, May 1 from Chicago to New Haven, returning Fri, May 8, priced at $115 found 5 days ago
Fri, Apr 24 - Mon, Apr 27
ORD
Chicago
HVN
New Haven
$123 Roundtrip, found 6 hours ago
$123
Roundtrip
found 6 hours ago
Select Avelo Airlines flight, departing Fri, Apr 24 from Chicago to New Haven, returning Mon, Apr 27, priced at $123 found 6 hours ago

New Milford economy flight packages

Price found within the past 48 hours. Click for updated prices.
Stamford Suites
4.0-star property

Stamford Suites

6.4/10 (105 reviews)

May 29 - Jun 1

3 night stay

Chicago (CHI) to White Plains (HPN)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $491, price is now $356 per person
$356
per person
found 1 day ago
Many positives aspects to Stamford Suites. It was clean - especially the kitchen and, yes, there is a full kitchen with gas stove, full sized refrigerator (!) and even a small dishwasher. The suite was very roomy. Location in Stamford is great! The staff is very accommodating. I slept extremely well there-bed was quite comfortable. If you are staying for awhile and need storage there are multiple closets! Rooms are bright with natural light - important to me. Yes, the hotel is a bit tired around the edges. The shower faucet was not brilliant. No coffee maker in room. But the positives outweigh the minor inconveniences!

Reviewed on Oct 28, 2025

Modern Luxury Home w GameRoom & Parking
3.5-star property

Modern Luxury Home w GameRoom & Parking

6.4/10 (6 reviews)

May 23 - May 25

2 night stay

Chicago (CHI) to White Plains (HPN)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,183, price is now $1,612 per person
$1,612
per person
found 1 day ago
The Armon Stamford Hotel & Conference
2.5-star property

The Armon Stamford Hotel & Conference

7.8/10 Good! (757 reviews)

May 25 - May 28

3 night stay

Chicago (CHI) to White Plains (HPN)

Delta • Coach

White Plains (HPN) to Chicago (CHI)

Spirit Airlines • Coach
Price was $502, price is now $382 per person
$382
per person
found 1 day ago
We were checked in to the room and only found out after making our way to the 3rd floor. We then had to go back to the elevator with our luggage and wait in line to get the correct room and then go BACK to the 3rd floor and find our room. The numbering system on this floor.is wack and we had to walk a pretty long way from the elevator to our room

Reviewed on Jan 5, 2026

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More About Flying To New Milford from Chicago

Route Information for Flights from Chicago to New Milford

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

Chicago to New Milford

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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.