$75 Cheap flight deals from Chicago (CHI) to Bridgeport (HPN)

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This Weekend's Flight Deals from Chicago to Bridgeport

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.

Fri, Sep 18 - Mon, Sep 21
ORD
O'Hare Intl.
HVN
Tweed - New Haven Regional
$150 Roundtrip, found 4 days ago
$150
Roundtrip
found 4 days ago
Select Avelo Airlines flight, departing Fri, Sep 18 from O'Hare Intl. to Tweed - New Haven Regional, returning Mon, Sep 21, priced at $150 found 4 days ago
Fri, Sep 18 - Sat, Sep 19
ORD
O'Hare Intl.
HPN
Westchester County
$494 Roundtrip, found 3 days ago
$494
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Sep 18 from O'Hare Intl. to Westchester County, returning Sat, Sep 19, priced at $494 found 3 days ago
Fri, Sep 18 - Sun, Sep 20
MDW
Midway Intl.
ISP
MacArthur
$937 Roundtrip, found 1 day ago
$937
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, Sep 18 from Midway Intl. to MacArthur, returning Sun, Sep 20, priced at $937 found 1 day ago

Airfares from $75 One Way, $150 Round Trip from Chicago to Bridgeport

Prices starting at $150 for return flights and $75 for one-way flights to Bridgeport were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Nov 19 - Sun, Nov 22
ORD
Chicago
HVN
New Haven
$150 Roundtrip, found 11 hours ago
$150
Roundtrip
found 11 hours ago
Select Avelo Airlines flight, departing Thu, Nov 19 from Chicago to New Haven, returning Sun, Nov 22, priced at $150 found 11 hours ago
Thu, Sep 17 - Mon, Sep 21
ORD
Chicago
HVN
New Haven
$152 Roundtrip, found 5 days ago
$152
Roundtrip
found 5 days ago
Select Avelo Airlines flight, departing Thu, Sep 17 from Chicago to New Haven, returning Mon, Sep 21, priced at $152 found 5 days ago
Fri, Oct 23 - Mon, Oct 26
ORD
Chicago
HVN
New Haven
$152 Roundtrip, just found
$152
Roundtrip
just found
Select Avelo Airlines flight, departing Fri, Oct 23 from Chicago to New Haven, returning Mon, Oct 26, priced at $152 just found
Thu, Oct 22 - Mon, Oct 26
ORD
Chicago
HVN
New Haven
$163 Roundtrip, found 22 hours ago
$163
Roundtrip
found 22 hours ago
Select Avelo Airlines flight, departing Thu, Oct 22 from Chicago to New Haven, returning Mon, Oct 26, priced at $163 found 22 hours ago
Thu, Oct 15 - Fri, Oct 23
ORD
Chicago
ISP
Islip
$336 Roundtrip, found 1 day ago
$336
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Oct 15 from Chicago to Islip, returning Fri, Oct 23, priced at $336 found 1 day ago

Bridgeport economy flight packages

Price found within the past 48 hours. Click for updated prices.
Landing Furnished Apartment Near Yale University
3.0-star property

Landing Furnished Apartment Near Yale University

2/10 (1 review)

Oct 22 - Oct 25

3 night stay

Chicago (ORD) to New Haven (HVN)

Xtra Airways • Roundtrip • Coach
Price was $711, price is now $588 per person
$588
per person
found 21 hours ago
Check in automated, but the key box was broken and it took me 30 on the phone with IT to get the keys. When I entered the apartment a water leak in the city had destroyed a chunk of the ceiling and there was a mess of drywall and dirty water on the floor. The firm tried to relocate me an hour away before promising to clean up and repair the problem while I was out, but maintenance never arrived. We had to book a hotel nearby. These people are incompetent

Reviewed on Sep 14, 2026

Luxury Furnished Apartments by Hyatus Downtown at Yale
3.5-star property

Luxury Furnished Apartments by Hyatus Downtown at Yale

9.6/10 Exceptional! (86 reviews)

Oct 18 - Oct 24

6 night stay

Chicago (ORD) to New Haven (HVN)

American Airlines • Coach

New Haven (HVN) to Chicago (ORD)

JetBlue Airways • Coach
Price was $1,617, price is now $1,305 per person
$1,305
per person
found 1 day ago
We recently stayed at Hyatus Downtown at Yale and had a good experience overall. The building is convenient and easy to access with a designated parking spot and the apartment unit felt modern, bright, and welcoming. Other highlights of the property are definitely the building amenities; having access to a fully equipped gym and a rooftop is a plus. The location is practical, positioned centrally between local businesses downtown New Haven, and some surrounding low-income blocks. To elevate the apartment to a true 5-star rating, a few maintenance and housekeeping details need attention. The throw blanket in the main room needed a proper wash before our arrival. The bathroom also felt somewhat average compared to the rest of the unit, the lighting was dim and needed a lighted mirror, while the vanity counter and tub/shower combo were somewhat worn down. Overall, it was a solid 4-star stay with great building features and a nice welcome bag with snacks.👍

Reviewed on Aug 16, 2026

Graduate by Hilton New Haven
4.0-star property

Graduate by Hilton New Haven

9.2/10 Wonderful! (1,001 reviews)

Oct 22 - Oct 25

3 night stay

Chicago (ORD) to New Haven (HVN)

Xtra Airways • Roundtrip • Coach
Price was $1,048, price is now $856 per person
$856
per person
found 21 hours ago

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More About Flying To Bridgeport from Chicago

Route Information for Flights from Chicago to Bridgeport

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

Chicago to Bridgeport

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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.