$44 Cheap flight deals from Chicago (CHI) to Brooklyn (NYC)

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This Weekend's Flight Deals from Chicago to Brooklyn

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.

Sun, Jun 1 - Mon, Aug 25
MDW
Midway Intl.
JFK
John F. Kennedy Intl.
$228 Roundtrip, found 1 day ago
$228
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Jun 1 from Midway Intl. to John F. Kennedy Intl., returning Mon, Aug 25, priced at $228 found 1 day ago
Sat, May 31 - Tue, Jun 3
ORD
O'Hare Intl.
JFK
John F. Kennedy Intl.
$245 Roundtrip, just found
$245
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, May 31 from O'Hare Intl. to John F. Kennedy Intl., returning Tue, Jun 3, priced at $245 just found
Sun, Jun 1 - Sat, Jun 14
MDW
Midway Intl.
LGA
LaGuardia
$254 Roundtrip, found 1 day ago
$254
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Jun 1 from Midway Intl. to LaGuardia, returning Sat, Jun 14, priced at $254 found 1 day ago
Sun, Jun 1 - Sat, Jun 7
ORD
O'Hare Intl.
LGA
LaGuardia
$299 Roundtrip, just found
$299
Roundtrip
just found
Select Spirit Airlines flight, departing Sun, Jun 1 from O'Hare Intl. to LaGuardia, returning Sat, Jun 7, priced at $299 just found

Airfares from $44 One Way, $87 Round Trip from Chicago to Brooklyn

Prices starting at $87 for return flights and $44 for one-way flights to Brooklyn were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Jun 17 - Wed, Jun 18
ORD
Chicago
EWR
New York
$87 Roundtrip, found 1 hour ago
$87
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, Jun 17 from Chicago to New York, returning Wed, Jun 18, priced at $87 found 1 hour ago
Tue, Jul 1 - Tue, Jul 8
ORD
Chicago
JFK
New York
$144 Roundtrip, just found
$144
Roundtrip
just found
Select JetBlue Airways flight, departing Tue, Jul 1 from Chicago to New York, returning Tue, Jul 8, priced at $144 just found
Thu, Jul 3 - Sat, Jul 5
ORD
Chicago
LGA
New York
$144 Roundtrip, found 1 hour ago
$144
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Thu, Jul 3 from Chicago to New York, returning Sat, Jul 5, priced at $144 found 1 hour ago
Wed, Aug 13 - Sat, Aug 16
MDW
Chicago
LGA
New York
$157 Roundtrip, found 5 hours ago
$157
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Wed, Aug 13 from Chicago to New York, returning Sat, Aug 16, priced at $157 found 5 hours ago
Tue, Jul 1 - Tue, Jul 8
MDW
Chicago
EWR
New York
$170 Roundtrip, found 5 days ago
$170
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Jul 1 from Chicago to New York, returning Tue, Jul 8, priced at $170 found 5 days ago

Brooklyn economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hilton Newark Airport
3.5-star property

Hilton Newark Airport

8.4/10 Very Good! (1,346 reviews)

Jun 29 - Jul 3

4 night stay

Chicago (CHI) to Newark Liberty Intl. Airport (EWR)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Was next to airport... I arrived at midnight and left at 5am so to be honest I did not experience anything but sleep which is what I needed.

Reviewed on Mar 5, 2025

Ruschmeyers Hotel
2.0-star property

Ruschmeyers Hotel

7.4/10 Good! (35 reviews)

Jul 24 - Jul 27

3 night stay

Chicago (ORD) to New York (JFK)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
1 Hotel Brooklyn Bridge
5.0-star property

1 Hotel Brooklyn Bridge

8.8/10 Excellent! (1,001 reviews)

Jul 16 - Jul 20

4 night stay

Chicago (CHI) to New York (JFK)

Spirit Airlines • Coach

New York (JFK) to Chicago (CHI)

United • Coach
per person
found 16 hours ago
The hotel is beautiful looking forward to visiting again.

Reviewed on Feb 21, 2023

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Brooklyn packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Now Now NoHo
2.0-star property

Now Now NoHo

8.2/10 Very Good! (59 reviews)

Jul 10 - Jul 13

3 night stay

Chicago (ORD) to New York (JFK)

Delta • PremiumEconomy

New York (JFK) to Chicago (ORD)

United • PremiumEconomy
per person
found 17 hours ago
Perfect place for solo travelers looking for a crash pad that’s inexpensive. Be sure to use the ear plugs and sound machine as the rooms have open ceilings and you can hear each time a door is opened or closed.

Reviewed on May 4, 2025

Hotel St. James
2.5-star property

Hotel St. James

8.6/10 Excellent! (6,006 reviews)

Jul 10 - Jul 13

3 night stay

Chicago (ORD) to New York (JFK)

Delta • PremiumEconomy

New York (JFK) to Chicago (ORD)

United • PremiumEconomy
per person
found 17 hours ago
Stayed here for a city weekend. The hotel has a great curb appeal and the public spaces- lobby, library, hallways were beautiful. The room, by contrast, was very clean but rather plainly decorated. I also found everything to be rather low- furniture, sink, commode- for me, I’m 5’10”. The room has a window AC unit which if you are using it means that you can’t close the shades and you can also hear all the street noise. I was on the 4th floor. Two things I wish were provided in the room were a clock and at least an ice bucket. That being said the staff was friendly and professional and you really can’t beat the location. You are right off Times Square within easy walking distance to theaters, restaurants and shopping. While there are no availability of drinks or snacks in the hotel there is a convenience store right next door and coffee place across the street if that’s your thing. Pricing, for the area, was very reasonable.

Reviewed on May 26, 2025

Hotel Stanford
3.0-star property

Hotel Stanford

8.6/10 Excellent! (1,351 reviews)

Jul 10 - Jul 13

3 night stay

Chicago (ORD) to New York (JFK)

Delta • PremiumEconomy

New York (JFK) to Chicago (ORD)

United • PremiumEconomy
per person
found 17 hours ago
I really like this little hotel, tucked in the heart of Korea Town and minutes from the bustle of Herald Square. The rooms are clean and spacious. The staff is super friendly and courteous. There's a breakfast room/lounge that feels like a cozy library and is a nice place to hang out if you're waiting for your room to be available or awaiting your trip back home. There can be a long wait for the one elevator if you're on a higher floor, so add a few minutes if you're on a schedule. This was my second stay here, and I would happily return to it again.

Reviewed on May 2, 2025

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Brooklyn first class flight packages

Price found within the past 48 hours. Click for updated prices.
The Benjamin Royal Sonesta New York
4.5-star property

The Benjamin Royal Sonesta New York

8.6/10 Excellent! (1,013 reviews)

Jul 20 - Jul 25

5 night stay

Chicago (CHI) to New York (JFK)

American Airlines • Roundtrip • FirstClass
per person
found 21 hours ago
I had forgotten how much I enjoy this property. Recent renovation is a big success and low-key vibe is much appreciated

Reviewed on Nov 18, 2024

The Fifth Avenue Hotel
5.0-star property

The Fifth Avenue Hotel

9.6/10 Exceptional! (97 reviews)

Jul 20 - Jul 25

5 night stay

Chicago (CHI) to New York (JFK)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
per person
found 21 hours ago
Park Lane New York
5.0-star property

Park Lane New York

8.6/10 Excellent! (1,492 reviews)

Jul 20 - Jul 25

5 night stay

Chicago (CHI) to New York (JFK)

American Airlines • Roundtrip • FirstClass
per person
found 21 hours ago
Food was good. Elevators did not work or they were very long lines for them and staff would not allow us to take the stairs even though we were willing to do so. AC was not very functional - room AC could not cool to the setpoint, even though it was not a very hot day. Bed was very comfortable. Shower had very good water pressure. Location was extremely convenient. Staff were helpful and pleasant.

Reviewed on May 10, 2025

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More About Flying To Brooklyn from Chicago

Route Information for Flights from Chicago to Brooklyn

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

Chicago to Brooklyn

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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.