$37 Find Cheap Flights from Chicago to Brooklyn

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Brooklyn departing on 5/13. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Cheap Flight Deals from Chicago to Brooklyn (CHI-NYC)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Brooklyn that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Chicago to Brooklyn

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Brooklyn.
Discover the best prices for you by selecting your travel dates on KAYAK.
Spirit Airlines Logo
5:51 am - 9:00 amORD-LGA
2h 09mnonstop
Spirit Airlines Logo
6:30 pm - 8:07 pmLGA-ORD
2h 37mnonstop
$55Spirit Airlines
Find Deal
Tue, Jun 3 - Wed, Jun 4
Spirit Airlines Logo
5:51 am - 9:00 amORD-LGA
2h 09mnonstop
Spirit Airlines Logo
6:30 pm - 8:07 pmLGA-ORD
2h 37mnonstop
$57Spirit Airlines
Find Deal
Tue, Jun 3 - Wed, Jun 4
Delta Logo
9:25 am - 12:39 pmORD-LGA
2h 14mnonstop
Delta Logo
8:30 am - 10:12 amLGA-ORD
2h 42mnonstop
$137Delta
Find Deal
Wed, May 14 - Wed, May 21
Delta Logo
7:00 am - 10:25 amORD-JFK
2h 25mnonstop
Delta Logo
3:30 pm - 5:29 pmJFK-ORD
2h 59mnonstop
$137Delta
Find Deal
Wed, May 14 - Wed, May 21
Southwest Logo
8:20 pm - 11:25 pmMDW-LGA
2h 05mnonstop
Southwest Logo
6:10 am - 7:30 amLGA-MDW
2h 20mnonstop
$137Southwest
Find Deal
Wed, May 14 - Wed, May 28
American Airlines Logo
4:44 pm - 8:00 pmORD-JFK
2h 16mnonstop
American Airlines Logo
9:00 am - 11:09 amJFK-ORD
3h 09mnonstop
$138American Airlines
Find Deal
Wed, May 14 - Wed, May 21
United Airlines Logo
8:00 pm - 11:18 pmORD-LGA
2h 18mnonstop
United Airlines Logo
6:25 am - 8:00 amLGA-ORD
2h 35mnonstop
$157United Airlines
Find Deal
Sat, May 17 - Wed, May 21
Southwest Logo
8:25 am - 11:35 amMDW-LGA
2h 10mnonstop
Southwest Logo
9:45 pm - 11:00 pmLGA-MDW
2h 15mnonstop
$157Southwest
Find Deal
Wed, May 28 - Wed, May 28
American Airlines Logo
8:29 pm - 11:59 pmORD-EWR
2h 30mnonstop
American Airlines Logo
7:00 am - 8:44 amEWR-ORD
2h 44mnonstop
$159American Airlines
Find Deal
Tue, Jul 8 - Wed, Jul 16
United Airlines Logo
4:25 pm - 11:30 pmORD-LGA
6h 05m1 stop
United Airlines Logo
9:30 am - 11:11 amLGA-ORD
2h 41mnonstop
$167United Airlines
Find Deal
Sat, May 17 - Wed, May 21
Useful Info

Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$37
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from Chicago O'Hare Airport to New York LaGuardia Airport

When to book flights from Chicago to Brooklyn

Are your dates flexible? Find out the best times to travel from Chicago to Brooklyn based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Flights from Chicago to Brooklyn: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew the route from Chicago to Brooklyn 
Verified travelerFlew with British AirwaysORD-EWRApr 2025
American Eagle definitely does not provide the same quality of service as American Airlines, even if they are operated by the later.
VictorFlew with Spirit AirlinesORD-LGAFeb 2025
Spirit landing at LGA makes life so easy to get to the city!
mauriceFlew with IberiaORD-JFKSep 2024
You should arrive early, take a lighht snack and be prepared for delays.
FreddyFlew with SouthwestMDW-LGAJul 2024
On a stormy day, be prepare for delays.
AlexanderFlew with Spirit AirlinesORD-LGAMay 2024
Know your connection options — specially when LaGuardia Airport (LGA) only has buses going to/from the airport to the rest of the city. Luckily, the one to the subway station (Q70) is free-of-charge to ride on!

FAQs for booking flights from Chicago to Brooklyn

  • Which airports will I be using when flying from Chicago to Brooklyn?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Brooklyn does not have its own airport so you’ll be flying into nearby New York All airports airport, which is 5.4 mi away.

  • How long does a flight from Chicago to Brooklyn take?

    Direct flights cover the 711 miles separating Chicago and Brooklyn in about 2h 05m.

  • How many flights are there between Chicago and Brooklyn?

    263 direct flights run between Chicago and Brooklyn on a daily basis. On average, there are about 1,846 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Brooklyn?

    Consider leaving on a Tuesday and avoid Saturdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Wednesdays and the most expensive ones on Saturdays.

  • How does KAYAK find such low prices on flights from Chicago to Brooklyn?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Brooklyn.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Brooklyn from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Brooklyn?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Brooklyn with an airline and back to Chicago with another airline.

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

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Brooklyn from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Brooklyn?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Brooklyn found on KAYAK was with Spirit Airlines for $37. Spirit Airlines offered a round-trip connection from $55 and JetBlue from $132.

Top tips for finding cheap flights from Chicago to Brooklyn

  • There is no airport in Brooklyn. Instead, you’ll be flying into New York All airports when flying between Chicago and Brooklyn.
  • The cheapest flight from Chicago to Brooklyn was found 27 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 November, December and January. The cheapest month to fly is September.

Top 5 airlines serving Chicago to Brooklyn

Need help choosing which airline to fly with from Chicago to Brooklyn? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4293 reviews
8.6Crew
8.0Comfort
7.1Food
7.6Entertainment
8.2Boarding
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Great staff. Wifi is terrible. Signing up for skylines is a painstaking process. Had to call customer service just to get my flight itinerary and confirmation sent to me. Consistent delays. A well staffed company that is run so poorly. Upper management needs to be renewed.

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Good and consistent Printer in lounge did not work for me :(

Flight heavily delayed. No food available despite purchasing an upgrade. No in cabin service.

It was not in Delta's control, but when we landed, we ended up parking at the wrong gate, and so everyone was already ready to deplane and had their carryon bags, ready to leave. But we had to sit down and move to the proper gate. This process took over 30 minutes. Again, not Delta's fault - more so on the staff at JFK

My Flight was cancelled and there was no other options available for me to Travel on that date and my options for the next day was all connecting flights that would have me in the airports all day before reaching my destination

First, the flight was schedule to leave at 12:08. Delayed to 12:38. It is 12:58 and I am sitting at the gate. The staff are not communicating with us (just tell me it’s gonna be five hours if that’s the case, quit hufflepuffing around like you’re trying to board us when the plane isn’t even here and you don’t know where your crew are. I’m still waiting for any communication about the further delay. This is a rebooked flight from a cancelled flight yesterday, when the airline failed to fulfill its fiduciary responsibility to hotel and cover transport for overnight cancelations. Asking about the food on the flight? What food?!? Delta doesn’t serve meals unless you pay for them and you really want me to give delta a high rating for passing out processed snacks (fun size!)? Can we be for real. Delta is cementing itself in history as one of the cheap, stingy, outdated, glory days are over airlines, and it shows. I took this flight knowing delta was going to provide below level service but this is beyond burgers!! I can’t believe a multi billion or dollar company looked straight in my eyes yesterday and I told me this wasn’t their fault and there for the extra cost in hotel and hundreds of dollars in Ubers are MY RESPONSIBILITY. The only thing I am at fault for is believing delta is reputable company worthy of my dollars. I’m not even sure I want to be compensated unless it is cash because I would rather die never traveling again than to put money in their pockets.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

All was good expecting the seats need a bit of cushion. Besides that I can’t complain.

The only positive is that the flight made it both ways. Getting charged for every little thing after the cost of the ticket itself is comical, considering how the plane and services are as bottom-tier as possible. The self check-in kiosks are useless. It’s nice to think that you can print your boarding pass, tag your checked bag, and then just drop it off. But no, they still make you go through the line once you finish- what’s the point of the self check-in then? Any questions for the staff seem like the biggest inconvenience and were met with condescending responses. This was my first and now last time ever flying with Spirit. After all the extra costs, subpar plane and staff, I see no value. I’d rather drive the 13 hours than give Spirit another dime.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

Very dissatisfied with spirit airlines after buying my ticket's they cancelled our flights with no reasoning.

Spirit is awful. Too expensive for what you get. Stop nickel and diming.

Seats are poor. They do not lean back. They do not even have pockets on the back, making it impossible to store a phone or a coke bottle. If you opt for basic economy cheap seats, they stick you always in the middle or window seat, even though there are unoccupied seats on the aisle. And then there is the nickel and diming. No carry-ons. And checking your carry-on is $70. At the end there is no price advantage but there is plenty of aggravation.

Good crew and safe. However, comfort and being nickeled-and-dimed are my issues. $75 each way for luggage is exhortation. The space to the next seat is so close you cannot open a laptop. The magazine rack doesn’t hold your items. Not a fan.

Everything on the flight was OK. However, the price is very deceiving the way that it is marketed. It seems like it’s going to be very low cost, but when you add in the charges for luggage, choosing a seat, food & drink, etc., that are already included in other competitors fares, it really is no cheaper, and possibly even more expensive than the other carriers. It actually makes your carrier seem dishonest.

The seats were comfortable and not as tight as i would have expected. Would have been nice to be able to recline my seat, which was not available. Some form of free snacks and drink option would be appreciated as well, even just a water and small bag of crackers would have been better than nothing at all.

Bad seats. Very uncomfortable. Crew was fine. Too much upcsharging

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