
$41 Cheap flight deals from Chicago (CHI) to Danbury (SWF)
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 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.
Airfares from $41 One Way, $78 Round Trip from Chicago to Danbury
Prices starting at $78 for return flights and $41 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.
Danbury economy flight packages

Luxury 3BR Family Home Game Room Parking
Apr 25 - Apr 27
Chicago (CHI) to White Plains (HPN)
White Plains (HPN) to Chicago (CHI)

Hampton Inn & Suites Yonkers
May 21 - May 24
Chicago (CHI) to White Plains (HPN)
Reviewed on Feb 20, 2026

Cromwell Manor Inn
Apr 30 - May 4
Chicago (CHI) to White Plains (HPN)
Reviewed on Aug 15, 2025
Danbury packages with premium economy flights

Norwalk Inn & Conference Center
May 8 - May 11
Chicago (ORD) to White Plains (HPN)
White Plains (HPN) to Chicago (ORD)
Reviewed on Oct 30, 2025

Westchester Marriott
May 8 - May 11
Chicago (ORD) to White Plains (HPN)
White Plains (HPN) to Chicago (ORD)
Reviewed on Sep 15, 2025

Sonesta White Plains Downtown
May 8 - May 11
Chicago (ORD) to White Plains (HPN)
White Plains (HPN) to Chicago (ORD)
Reviewed on Jan 4, 2026
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
If you are looking online for bargain Chicago to Danbury flights, Orbitz is your ideal destination. We understand that vacations can be expensive and offer guaranteed low prices on our domestic and international tickets.
Orbitz Uses Cutting-Edge Mobile Tools
Orbitz may offer low cost Chicago to Danbury flights but this does not mean that we skimp on giving you the latest mobile apps. You don’t have to worry about checking your flight status as we send the info for your flights from Chicago to Danbury directly to your smartphone.
Fly Cheap and Earn Miles on Your Chicago to Danbury Flights
Frequent flyer miles and points are great—and even better when you earn them on cheap flights from Chicago to Danbury. With Orbitz, you can earn miles for your frequent flyer program on qualified flights. Enter your frequent flyer number when you book with us to get rewarded for your flight.
Orbitz Takes the Hassle Out Of Flying
We know that flying can be stressful, particularly if you are traveling with young children. That’s why we make sure you are aware of any changes or delays to your flights from Chicago to Danbury via your phone or email address. We can even inform family members too.
Orbitz Flights Fit Around Your Lifestyle
Orbitz understands that you don’t necessarily want to fly at 5:00 a.m—and that sometimes you do. This is why we allow you to find the best Chicago to Danbury flights at the times you want with ease.
Flights from Chicago
- Chicago to Orlando
- Chicago to Houston
- Chicago to New York
- Chicago to Phoenix
- Chicago to Dallas
- Chicago to Los Angeles
- Chicago to New Orleans
- Chicago to London
- Chicago to Washington
- Chicago to Paris
- Chicago to Toronto
- Chicago to Rome
- Chicago to San Francisco
- Chicago to Cleveland
- Chicago to Detroit
- Chicago to Montreal
- Chicago to Sacramento
- Chicago to Kansas City
- Chicago to Hartford
- Chicago to Atlantic City
Danbury Airports
More Destinations
- Flights from Detroit (DTW) to Danbury (DXR)
- Flights from New York (LGA) to Danbury (DXR)
- Flights from Baltimore (MTN) to Danbury (DXR)
- Flights from Chicago (ORD) to Danbury (DXR)
- Flights from Columbus to Southbury
- Flights from Los Angeles to Southbury
- Flights from Raleigh to Southbury
- Flights from Richmond to Southbury
- Flights from Tampa to Southbury
- Flights from Monroe to Shelton
- Flights from Greenville - Spartanburg to Shelton
- Flights from Dallas to Trumbull
- Flights from Miami to Trumbull
- Flights from Minneapolis - St. Paul to Trumbull
- Flights from New Orleans to Trumbull
- Flights from New York to Trumbull
- Flights from Toronto to Trumbull
- Flights from Newark to Trumbull
- Flights from Richmond to Trumbull
- Flights from Milwaukee to Trumbull
- Flights from Madison to Trumbull
- Flights from Sarasota to Trumbull
- Flights from Springfield to Trumbull
- Flights from Akron to Trumbull
- Flights from Port Charlotte to Trumbull
- Flights from Charlottesville to Trumbull
- Flights from Bucharest to Trumbull
- Flights from Minneapolis - St. Paul to Westport
- Flights from Des Moines to Westport
- Flights from Pensacola to Westport
- Flights from Greenville - Spartanburg to Westport
- Flights from Duluth to Bridgeport
- Flights from Elmira to Bridgeport
- Flights from El Paso to Bridgeport
- Flights from Jackson to Bridgeport
- Flights from Anchorage to Bridgeport
- Flights from Cincinnati to Bridgeport
- Flights from Las Vegas to Bridgeport
- Flights from Lima to Bridgeport
- Flights from Memphis to Bridgeport
- Flights from Phoenix to Bridgeport
- Flights from Portland to Bridgeport
- Flights from Seattle to Bridgeport
- Flights from St. Louis to Bridgeport
- Flights from Charleston to Bridgeport
- Flights from Palm Springs to Bridgeport
- Flights from Jacksonville to Bridgeport
- Flights from Traverse City to Bridgeport
- Flights from Tyler to Bridgeport
- Flights from Pittsburgh to Bridgeport
- Flights from Tulsa to Bridgeport
- Flights from Pensacola to Bridgeport
- Flights from South Bend to Bridgeport
- Flights from Daytona Beach to Bridgeport
- Flights from Bentonville - Fayetteville to Bridgeport
- Flights from Milwaukee to Bridgeport
- Flights from Sarasota to Bridgeport
- Flights from Shreveport to Bridgeport
- Flights from Louisville to Bridgeport
- Flights from Lexington to Bridgeport
- Flights from Grand Rapids to Bridgeport
- Flights from Princeton to Bridgeport
- Flights from Augusta to Bridgeport
- Flights from Fayetteville to Bridgeport
- Flights from Gainesville to Bridgeport
- Flights from Tallahassee to Bridgeport
- Flights from Guatemala City to Bridgeport
- Flights from Johnstown to Bridgeport
- Flights from State College to Bridgeport
- Flights from Fort Smith to Bridgeport
- Flights from Fargo to Bridgeport
- Flights from Covington to Bridgeport
- Flights from Bozeman to Bridgeport
- Flights from Green Bay to Norwalk
- Flights from Guayaquil to Norwalk
- Flights from Jackson to Norwalk
- Flights from Nashville to Norwalk
- Flights from Cape Town to Norwalk
- Flights from Bozeman to Norwalk
- Flights from Guayaquil to New Milford
- Flights from Calgary to New Milford
- Flights from Charlotte to New Milford
- Flights from Chicago to New Milford
- Flights from Columbus to New Milford
- Flights from Detroit to New Milford
- Flights from Nashville to New Milford
- Flights from Portland to New Milford
- Flights from Raleigh to New Milford
- Flights from San Antonio to New Milford
- Flights from San Francisco to New Milford
- Flights from Washington to New Milford
- Flights from Palm Springs to New Milford
- Flights from Pittsburgh to New Milford
- Flights from Daytona Beach to New Milford
- Flights from Oklahoma City to New Milford
- Flights from Jacksonville to New Milford
- Flights from Puerto Plata to New Milford
- Flights from Newport News to New Milford
- Flights from Charlottesville to New Milford
- Flights from Columbia to New Milford
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.


