$155 Cheap flight deals from Chicago (CHI) to Danbury (SWF)

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This Weekend's Flight Deals from Chicago to Danbury

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, Nov 15 - Mon, Nov 24
ORD
O'Hare Intl.
HPN
Westchester County
$424 Roundtrip, found 4 days ago
$424
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Nov 15 from O'Hare Intl. to Westchester County, returning Mon, Nov 24, priced at $424 found 4 days ago

Airfares from $155 One Way, $337 Round Trip from Chicago to Danbury

Prices starting at $337 for return flights and $155 for one-way flights to Danbury were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Jan 5 - Thu, Jan 22
ORD
Chicago
HPN
White Plains
$337 Roundtrip, found 3 days ago
$337
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Jan 5 from Chicago to White Plains, returning Thu, Jan 22, priced at $337 found 3 days ago
Sat, Jan 10 - Thu, Jan 22
ORD
Chicago
HPN
White Plains
$342 Roundtrip, found 3 days ago
$342
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Jan 10 from Chicago to White Plains, returning Thu, Jan 22, priced at $342 found 3 days ago
Tue, Dec 30 - Sun, Jan 18
ORD
Chicago
HPN
White Plains
$353 Roundtrip, found 3 days ago
$353
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Dec 30 from Chicago to White Plains, returning Sun, Jan 18, priced at $353 found 3 days ago
Sat, Dec 13 - Sat, Dec 20
ORD
Chicago
HPN
White Plains
$355 Roundtrip, found 4 days ago
$355
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Dec 13 from Chicago to White Plains, returning Sat, Dec 20, priced at $355 found 4 days ago
Wed, Dec 24 - Tue, Jan 6
ORD
Chicago
HPN
White Plains
$358 Roundtrip, found 3 days ago
$358
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Dec 24 from Chicago to White Plains, returning Tue, Jan 6, priced at $358 found 3 days ago

Danbury economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Yonkers
2.5-star property

Hampton Inn & Suites Yonkers

8.2/10 Very Good! (1,583 reviews)

Dec 10 - Dec 14

4 night stay

Chicago (CHI) to White Plains (HPN)

Spirit Airlines • Coach

White Plains (HPN) to Chicago (CHI)

United • Coach
Save 100% on your flight
Price was $532, price is now $364 per person
$364
per person
found 1 day ago
Close to restaurants and shopping. Easy parking. Room was fantastic. Bathroom was very nice. Very clean. Very impressed.

Reviewed on Apr 22, 2025

Stamford Suites
4.0-star property

Stamford Suites

5.8/10 (64 reviews)

Dec 24 - Dec 27

3 night stay

Chicago (CHI) to White Plains (HPN)

Spirit Airlines • Roundtrip • Coach
Price was $468, price is now $378 per person
$378
per person
found 8 hours 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

Hyatt Regency Greenwich
4.0-star property

Hyatt Regency Greenwich

8.2/10 Very Good! (1,017 reviews)

Dec 19 - Dec 22

3 night stay

Chicago (CHI) to White Plains (HPN)

Spirit Airlines • Roundtrip • Coach
Price was $497, price is now $407 per person
$407
per person
found 1 day ago
This is our 8th or 9th stay with you as we have family in Old Greenwich. The renovations are welcomed and it's nice to have dining once again at the hotel. There is not enough staff at the restaurant/bar area though. We had to add our drinks at the reception desk because no one came to bring us our check on the evening of 6/27/25. Also the back entrance from the parking area needs to be kept swept and clean.

Reviewed on Jul 1, 2025

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More About Flying To Danbury from Chicago

Route Information for Flights from Chicago to Danbury

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

Chicago to Danbury

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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.