Find cheap flights from New Haven to Chicago

HVN - CHI

Find cheap flights from New Haven to Chicago

Round-trip
Economy
New Haven (HVN)
Chicago All airports
Fri 2/26
Fri 3/5
Any month
Compare vs. KAYAK |
Search hundreds of travel sites at once for deals on flights to Chicago

Good to know

Low season

June Best time to beat the crowds with an average 37% drop in price.

High season

March Most popular time to fly with an average 34% increase in price.

Average price round-trip

$278 (avg. price over the last 2 weeks)

Good deal round-trip

$227 or less

Good deal one-way

$143 or less

When to book flights from New Haven to Chicago

Estimated round-trip price
Average price per month
Flight prices as travel date approaches

Top tips for finding a cheap flight

  • Looking for a cheap flight? 25% of our users found flights on this route for $143 or less one-way and $227 or less round-trip.
  • The cheapest flight from New Haven to Chicago was found 43 days before departure, on average.
  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be February, March and April. The cheapest month to fly is June.

FAQs for booking flights from New Haven to Chicago

Are there Chicago travel restrictions currently due to Coronavirus?

How long does a flight from New Haven to Chicago take?

Which airlines provide the cheapest flights from New Haven to Chicago?

Do I need a passport to fly between New Haven and Chicago?

What’s the cheapest day of the week to fly from New Haven to Chicago?

Which airports will I be using when flying from New Haven to Chicago?

How does KAYAK find such low prices on flights from New Haven to Chicago?

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from New Haven to Chicago?

What is the Hacker Fare option on flights from New Haven to Chicago?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from New Haven to Chicago?

Top airline flying New Haven Tweed-New Haven to Chicago

Scores according to KAYAK customer reviews

7.2
American Airlines
Overall score based on 45,139 reviews
7.5
Boarding
7.1
Comfort
7.8
Crew
6.8
Entertainment
6.7
Food
Airline reviews

Pros: "The service was fantastic and so was the food!!!!! Loved the movie options as well."

Pros: "All good, except poor prep on food"
Cons: "As above"

Pros: "Not much"
Cons: "Seating horrible"

Pros: "Over a hour late"
Cons: "Over a hour late"

Cons: "Seating ---- to tight"

Pros: "Newest aircraft, great customer service"
Cons: "Nothing"

Cons: "Seats are hard, narrow and generally uncomfortable."

Pros: "On time and arrived early!"

Cons: "Seats are getting more and more uncomfortable"

Cons: "gate assignment took too long"

Pros: "We liked the effiency and politeness of the staff. We enjoyed the movies, the food was better than normal."
Cons: "We were very unhappy at having to pay extra for our seats after we had booked the airfare. Especially on the way to Paris when there were so many extra available seats! I counted 50 available seats!"

Pros: "Cerainly boarding is easy and the seats are quite comfort in business class."
Cons: "the service, considering this was the highest level of service on these flights was less than I would have expected"

Cons: "Horrible long delays."

Cons: "The seats were so close together! I was between two men, and one was spitting tabaco into a cup. It was terrible."

Cons: "Not much offered on domestic flights."

Pros: "Nothing"
Cons: "Personnel; lack of customer service"

Cons: "Kayak repeatedly listed the departure gate as D36 when it was D17."

Cons: "It was cancelled"

Cons: "The tsa in chicago was very unorganized. The tsa workers were extremely rude."

Pros: "On time"
Cons: "Very cold on board"

Pros: "Was able to store my carry on and arrived early"

Pros: "Individual entertainment. Wowww!"
Cons: "Seat was a bit tiny. Free food snacks were not quite good."

Cons: "Lots of time changes. 1 piece of luggage sent wrong destination."

Pros: "AA Dreamliner was awesome"
Cons: "Holding terminal had no food establishments"

Pros: "Quick and easy boarding"
Cons: "Uncomfortable seats"

Pros: "Great service and friendly stafg"
Cons: "Loved the yourt for breakfadt...rest of it was ok"

Pros: "Fact we got there"
Cons: "Poor customer handling at Laguardia and no info why we were being delayed."

Pros: "The service and the food was great and getting to watch new release movies was a pleasant bonus"
Cons: "We did not get the seats we purchased but we did get a refund"

Pros: "Fast boarding."
Cons: "Slow on return of gate checked bags. A little late in getting off the ground."

Cons: "No power outlets. A bag of chips in 1st class is pretty weak. Compared to Europe flights we can from, aircraft felt like 1960's Aeroflot."

Pros: "Badly handled dealy situation"
Cons: "Airplane very clean like new"

Pros: "Only 30 minutes or so to ORD from GRB Paid with AA points at 7,500 miles each way for a weekend in Chicago"

Cons: "Paid for extra legroom, got a seat that didn't recline :("

Pros: "Everything was on time and luggage arrived at my final destination"
Cons: "Free wifi would be amazing :)"

Cons: "."

Pros: "Great attendants. Easy ride. Easy take off, easy landing."
Cons: "We departed late due to something going on in the runway. No free wifi option."

Pros: "Good air and great stewardesses"

Pros: "Smooth"

Pros: "Nothing"
Cons: "Everything"

Pros: "wifi was great"

Pros: "Fast check in, timely take off & arrival Excellent and friendly service"
Cons: "NA"

Pros: "Worst experience food is very bad"

Pros: "The staff were very friendly and informative"
Cons: "It felt a bit cramped, but overall nice seats and movie screens"

Pros: "1/2 empty"

Pros: "Staff members went above and beyond expections; accomodating some seating reassignment requests, charging customer phones, and being very responsive overall."
Cons: "It would have been nice to at least have USB chargers in economy class."

Pros: "On time"
Cons: "All well"

Pros: "On time. Friendly."

Cons: "Very late"

Pros: "Sears had more room than as medal, service and hospitality much improved over as. Dinner and breakfast were scrumptious and drink choices were abundant."

Read more about American Airlines
COVID-19 information

Safety measures for airlines flying from New Haven to Chicago

Airlines flying from New Haven to Chicago have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from New Haven to Chicago

Mandatory masks

Masks required on board, masks provided on flights from New Haven to Chicago

Social distancing seating

Middle seats unavailable to book on flights from New Haven to Chicago

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from New Haven to Chicago

Book cheap flights from New Haven to Chicago

Recent round-trip flight & train deals

3/18
Thu
1 stop
American Airlines
4h 50m
HVN - ORD
3/25
Thu
1 stop
American Airlines
5h 38m
ORD - HVN
3/23
Tue
2 stops
American Airlines
28h 14m
HVN - ORD
3/29
Mon
1 stop
American Airlines
5h 38m
ORD - HVN
3/27
Sat
2 stops
American Airlines
24h 24m
HVN - ORD
3/29
Mon
1 stop
American Airlines
5h 38m
ORD - HVN
3/7
Sun
1 stop
Amtrak
23h 50m
ZVE - ZUN
3/11
Thu
1 stop
Amtrak
24h 00m
ZUN - ZVE
3/21
Sun
1 stop
American Airlines
14h 02m
HVN - ORD
3/29
Mon
1 stop
American Airlines
5h 38m
ORD - HVN
3/6
Sat
1 stop
Amtrak
34h 10m
ZVE - ZUN
3/11
Thu
1 stop
Amtrak
21h 45m
ZUN - ZVE
3/22
Mon
1 stop
American Airlines
4h 50m
HVN - ORD
3/28
Sun
2 stops
American Airlines
26h 38m
ORD - HVN
3/23
Tue
2 stops
American Airlines
22h 17m
HVN - ORD
3/28
Sun
2 stops
American Airlines
21h 22m
ORD - HVN
3/11
Thu
1 stop
American Airlines
4h 50m
HVN - ORD
3/15
Mon
1 stop
American Airlines
5h 38m
ORD - HVN
3/21
Sun
1 stop
American Airlines
14h 02m
HVN - ORD
3/28
Sun
2 stops
American Airlines
26h 38m
ORD - HVN
3/5
Fri
2 stops
Amtrak
21h 10m
ZVE - ZUN
3/13
Sat
1 stop
Amtrak
23h 14m
ZUN - ZVE
3/5
Fri
2 stops
Amtrak
21h 10m
ZVE - ZUN
3/11
Thu
1 stop
Amtrak
23h 10m
ZUN - ZVE
3/26
Fri
2 stops
American Airlines
14h 02m
HVN - ORD
3/28
Sun
2 stops
American Airlines
21h 22m
ORD - HVN
3/27
Sat
1 stop
American Airlines
14h 02m
HVN - ORD
3/28
Sun
1 stop
American Airlines
5h 38m
ORD - HVN
3/7
Sun
1 stop
American Airlines
4h 50m
HVN - ORD
3/12
Fri
1 stop
American Airlines
5h 38m
ORD - HVN
3/22
Mon
1 stop
American Airlines
4h 50m
HVN - ORD
3/29
Mon
2 stops
American Airlines
7h 33m
ORD - HVN
3/4
Thu
1 stop
American Airlines
19h 02m
HVN - ORD
3/7
Sun
2 stops
American Airlines
21h 08m
ORD - HVN
3/4
Thu
2 stops
American Airlines
18h 52m
HVN - ORD
3/7
Sun
2 stops
American Airlines
21h 08m
ORD - HVN
3/4
Thu
1 stop
American Airlines
4h 50m
HVN - ORD
3/7
Sun
1 stop
American Airlines
5h 38m
ORD - HVN
Show more results

Recent one-way flight & bus deals

3/18
Thu
1 stop
American Airlines
4h 50m
HVN - ORD
3/19
Fri
1 stop
American Airlines
4h 50m
HVN - ORD
4/5
Mon
2 stops
Multiple Airlines
30h 05m
ZVE - F99
3/8
Mon
1 stop
American Airlines
4h 50m
HVN - ORD
3/6
Sat
1 stop
American Airlines
19h 02m
HVN - ORD
3/4
Thu
1 stop
American Airlines
4h 50m
HVN - ORD
Show more results

Compare transportation modes for New Haven to Chicago

Average price
Flights $236
Trains $237
-
1
  • Round-trip
  • One-way
  • Multi-city
  • Trip Builder
  • Economy
  • Premium Economy
  • Business
  • First
  • Multiple
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First