New York to Chicago EWR, JFK, LGA → MDW, ORD, RFD
Newark Liberty International Airport (EWR), John F. Kennedy International Airport (JFK), LaGuardia Airport (LGA) → Chicago Midway International Airport (MDW), O'Hare International Airport (ORD), Chicago Rockford International Airport (RFD)
The cheapest return found recently is $254 with United Airlines, 4 Dec – 6 Dec, found yesterday. The cheapest one-way found recently is $164 with American Airlines, 20 Dec, found yesterday.
Return
The cheapest return fare on each of 27 departure dates is usually $268 to $321.
Cheapest return found recently
$254
4 Dec – 6 Dec · United Airlines
Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD)
Leaves 12:37 p.m. · Return leaves 5:55 a.m. · 4 h 53 min of travel, both ways together
out nonstop, back nonstop
found yesterday
Cheapest nonstop return
$254
4 Dec – 6 Dec · United Airlines
Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD)
Leaves 12:37 p.m. · Return leaves 5:55 a.m. · 4 h 53 min of travel, both ways together
out nonstop, back nonstop
found yesterday
Every nonstop date from New York to Chicago
Found recently, and the cheapest we hold
$254 4 Dec – 6 Decfound yesterdaySee prices for these dates
$218 7 Nov – 13 Novfound 3 days agoSee prices for these dates
What have prices looked like?
Over 25 days, 24 Sept to 18 Oct, the cheapest return we saw each day was $168 to $243.
At $254, the cheapest return found recently is above that range.
25 days is a short history, so treat this range as an early guide.
Those were the prices on those days, not today's.
Is this a good return price?
Compared with the cheapest return fare on each of 27 departure dates from 20 Oct to 11 Sept 2027, found by travelers' searches in the last 7 days (economy, the price the seller showed on Aviasales). The usual range is the middle half of those prices.
Could nearby dates be cheaper?
We hold no other 2-night return fares leaving within 3 days of 4 Dec to compare.
Every date we hold
332 fares on 27 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 20 Oct – 22 Oct | $292 | Frontier Airlines | Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD) | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| 21 Oct – 24 Oct | $282 | Frontier Airlines | LaGuardia Airport (LGA) → Chicago Midway International Airport (MDW) | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| 22 Oct – 24 Oct | $326 | Frontier Airlines | Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD) | out 1 stop, back 1 stop | found 2 days ago | See prices for these dates |
| 24 Oct – 27 Oct | $309 | Frontier Airlines | LaGuardia Airport (LGA) → Chicago Midway International Airport (MDW) | out 1 stop, back 1 stop | found 3 days ago | See prices for these dates |
| 28 Oct – 31 Oct | $265 | Frontier Airlines | LaGuardia Airport (LGA) → O'Hare International Airport (ORD) | out 1 stop, back 1 stop | found 2 days ago | See prices for these dates |
| 31 Oct – 2 Nov | $286 | Frontier Airlines | LaGuardia Airport (LGA) → O'Hare International Airport (ORD) | out 1 stop, back 1 stop | found 4 days ago | See prices for these dates |
| 1 Nov – 6 Nov | $321 | American Airlines | John F. Kennedy International Airport (JFK) → O'Hare International Airport (ORD) | out nonstop, back nonstop | found 6 hours ago | See prices for these dates |
| 2 Nov – 10 Nov | $278 | United Airlines | LaGuardia Airport (LGA) → O'Hare International Airport (ORD) | out nonstop, back nonstop | found 6 days ago | See prices for these dates |
| 3 Nov – 11 Nov | $229 | Frontier Airlines | Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD) | out 1 stop, back 1 stop | found 7 days ago | See prices for these dates |
| 5 Nov – 8 Nov | $316 | United Airlines | Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD) | out nonstop, back nonstop | found 4 days ago | See prices for these dates |
| 6 Nov – 8 Nov | $321 | United Airlines | Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD) | out nonstop, back nonstop | found 4 days ago | See prices for these dates |
| 7 Nov – 13 Nov | $218 | United Airlines | Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD) | out nonstop, back nonstop | found 3 days ago | See prices for these dates |
| 12 Nov – 15 Nov | $331 | American Airlines | John F. Kennedy International Airport (JFK) → O'Hare International Airport (ORD) | out nonstop, back nonstop | found 6 days ago | See prices for these dates |
| 17 Nov – 24 Nov | $307 | Frontier Airlines | Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD) | out 1 stop, back 1 stop | found 4 days ago | See prices for these dates |
| 20 Nov – 26 Nov | $255 | Frontier Airlines | Newark Liberty International Airport (EWR) → Chicago Midway International Airport (MDW) | out 1 stop, back 1 stop | found 5 days ago | See prices for these dates |
| 4 Dec – 6 Dec | $254 | United Airlines | Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD) | out nonstop, back nonstop | found yesterday | See prices for these dates |
| 9 Dec – 12 Dec | $257 | Frontier Airlines | Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD) | out 1 stop, back 1 stop | found yesterday | See prices for these dates |
| 10 Dec – 15 Dec | $249 | Frontier Airlines | LaGuardia Airport (LGA) → O'Hare International Airport (ORD) | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| 12 Dec – 9 Jan 2027 | $299 | Southwest Airlines | LaGuardia Airport (LGA) → Chicago Midway International Airport (MDW) | out nonstop, back 1 stop | found 6 days ago | See prices for these dates |
| 29 Dec – 1 Jan 2027 | $304 | United Airlines | LaGuardia Airport (LGA) → O'Hare International Airport (ORD) | out nonstop, back nonstop | found 5 days ago | See prices for these dates |
| 4 Jan 2027 – 6 Jan 2027 | $309 | Southwest Airlines | LaGuardia Airport (LGA) → Chicago Midway International Airport (MDW) | out nonstop, back nonstop | found 5 days ago | See prices for these dates |
| 28 Jan 2027 – 1 Feb 2027 | $270 | Frontier Airlines | Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD) | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| 5 Feb 2027 – 5 Feb 2027 | $282 | Frontier Airlines | LaGuardia Airport (LGA) → O'Hare International Airport (ORD) | out 1 stop, back 1 stop | found 3 days ago | See prices for these dates |
| 3 Mar 2027 – 24 Mar 2027 | $342 | Frontier Airlines | LaGuardia Airport (LGA) → O'Hare International Airport (ORD) | out 1 stop, back nonstop | found yesterday | See prices for these dates |
| 13 Mar 2027 – 19 Mar 2027 | $377 | United Airlines | Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD) | out nonstop, back nonstop | found yesterday | See prices for these dates |
| 20 Apr 2027 – 26 Apr 2027 | $323 | American Airlines | John F. Kennedy International Airport (JFK) → O'Hare International Airport (ORD) | out nonstop, back nonstop | found 5 days ago | See prices for these dates |
| 11 Sept 2027 – 14 Sept 2027 | $396 | American Airlines | Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD) | out nonstop, back nonstop | found yesterday | See prices for these dates |
Which month looks cheapest?
November 2026 is the cheapest month — from $218.
Airlines on the cheapest dates: Frontier Airlines, United Airlines, American Airlines, Southwest Airlines.
One-way
The cheapest one-way fare on each of 22 departure dates is usually $131 to $174.
Cheapest one-way found recently
$164
20 Dec · American Airlines
Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD)
Leaves 5:07 a.m. · 3 h 3 min trip
nonstop
found yesterday
Cheapest nonstop one-way
$164
20 Dec · American Airlines
Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD)
Leaves 5:07 a.m. · 3 h 3 min trip
nonstop
found yesterday
Every nonstop date from New York to Chicago
Found recently, and the cheapest we hold
$164 20 Decfound yesterdayOpen this trip
$114 12 Decfound 6 days agoOpen this trip
What have prices looked like?
Over 25 days, 24 Sept to 18 Oct, the cheapest one-way we saw each day was $88 to $129.
At $164, the cheapest one-way found recently is above that range.
25 days is a short history, so treat this range as an early guide.
Those were the prices on those days, not today's.
Is this a good one-way price?
Compared with the cheapest one-way fare on each of 22 departure dates from 20 Oct to 23 Jul 2027, found by travelers' searches in the last 7 days (economy, the price the seller showed on Aviasales). The usual range is the middle half of those prices.
Could nearby dates be cheaper?
We hold no other one-way fares leaving within 3 days of 20 Dec to compare.
Every date we hold
183 fares on 22 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 20 Oct | $126 | Frontier Airlines | Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD) | 1 stop | found 6 days ago | Open this trip |
| 27 Oct | $127 | Frontier Airlines | LaGuardia Airport (LGA) → O'Hare International Airport (ORD) | 1 stop | found 2 days ago | Open this trip |
| 27 Nov | $187 | United Airlines | LaGuardia Airport (LGA) → O'Hare International Airport (ORD) | nonstop | found 6 days ago | Open this trip |
| 12 Dec | $114 | Frontier Airlines | Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD) | 1 stop | found 6 days ago | Open this trip |
| 13 Dec | $132 | United Airlines | Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD) | nonstop | found 5 days ago | Open this trip |
| 20 Dec | $164 | American Airlines | Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD) | nonstop | found yesterday | Open this trip |
| 24 Dec | $159 | American Airlines | John F. Kennedy International Airport (JFK) → O'Hare International Airport (ORD) | nonstop | found 5 days ago | Open this trip |
| 29 Dec | $143 | United Airlines | Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD) | nonstop | found 5 days ago | Open this trip |
| 1 Jan 2027 | $161 | American Airlines | John F. Kennedy International Airport (JFK) → O'Hare International Airport (ORD) | nonstop | found 3 days ago | Open this trip |
| 4 Jan 2027 | $152 | Southwest Airlines | LaGuardia Airport (LGA) → Chicago Midway International Airport (MDW) | nonstop | found 5 days ago | Open this trip |
| 7 Jan 2027 | $128 | United Airlines | Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD) | nonstop | found 5 days ago | Open this trip |
| 14 Jan 2027 | $129 | Frontier Airlines | Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD) | 1 stop | found 3 days ago | Open this trip |
| 5 Feb 2027 | $131 | United Airlines | Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD) | nonstop | found 3 days ago | Open this trip |
| 22 Mar 2027 | $174 | American Airlines | Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD) | nonstop | found yesterday | Open this trip |
| 23 Mar 2027 | $177 | American Airlines | Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD) | nonstop | found 2 days ago | Open this trip |
| 27 Mar 2027 | $165 | United Airlines | Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD) | nonstop | found yesterday | Open this trip |
| 3 Apr 2027 | $166 | United Airlines | Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD) | nonstop | found 3 days ago | Open this trip |
| 9 Apr 2027 | $176 | American Airlines | LaGuardia Airport (LGA) → O'Hare International Airport (ORD) | nonstop | found 3 days ago | Open this trip |
| 12 Apr 2027 | $161 | American Airlines | Newark Liberty International Airport (EWR) → O'Hare International Airport (ORD) | nonstop | found 5 days ago | Open this trip |
| 24 May 2027 | $174 | American Airlines | John F. Kennedy International Airport (JFK) → O'Hare International Airport (ORD) | nonstop | found 6 days ago | Open this trip |
| 16 Jul 2027 | $177 | American Airlines | LaGuardia Airport (LGA) → O'Hare International Airport (ORD) | nonstop | found 2 days ago | Open this trip |
| 23 Jul 2027 | $177 | American Airlines | LaGuardia Airport (LGA) → O'Hare International Airport (ORD) | nonstop | found 2 days ago | Open this trip |
Which month looks cheapest?
December 2026 is the cheapest month — from $114.
Airlines on the cheapest dates: American Airlines, United Airlines, Frontier Airlines, Southwest Airlines.
Premium cabin fares from New York to Chicago
Return
We looked for premium economy, business and first-class return fares on this route, and hold none found in the last 7 days.
Today's prices for 4 Dec – 6 Dec in another cabin: Premium economy · Business · First
One-way
Premium economy
The lowest premium economy fare we have seen is $309, on one departure date.
14 Jan 2027 · LGA → ORD · American Airlines
nonstop
found 3 days ago
Today's prices for 20 Dec in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for New York to Chicago?
Return
Fares 30 to 59 days before departure were typically 23% lower than 0 to 6 days before departure.
From the cheapest return each day between 24 Sept and 18 Oct (25 days), grouped by how many days ahead the flight left; one adult in economy.
Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.
Prices reflect recent searches — current fares may differ.
See these ranges as a table
| Booked ahead by | Typical fare | Cheapest day | Above the cheapest | Days of prices |
|---|---|---|---|---|
| 0–6 days | $250 | $246 | +30% | 25 |
| 7–13 days | $257 | $240 | +33% | 25 |
| 14–29 days | $218 | $168 | +13% | 25 |
| 30–59 days | $193 | $180 | Cheapest seen | 25 |
| 60–89 days | $267 | $239 | +38% | 25 |
| 90–179 days | $273 | $239 | +42% | 25 |
| 180+ days | $287 | $270 | +49% | 25 |
One-way
Fares 14 to 29 days before departure were typically 22% lower than 0 to 6 days before departure.
From the cheapest one-way each day between 24 Sept and 18 Oct (25 days), grouped by how many days ahead the flight left; one adult in economy.
Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.
Prices reflect recent searches — current fares may differ.
See these ranges as a table
| Booked ahead by | Typical fare | Cheapest day | Above the cheapest | Days of prices |
|---|---|---|---|---|
| 0–6 days | $126 | $119 | +29% | 22 |
| 7–13 days | $129 | $94 | +31% | 22 |
| 14–29 days | $98 | $88 | Cheapest seen | 19 |
| 30–59 days | $114 | $96 | +16% | 25 |
| 60–89 days | $125 | $95 | +28% | 25 |
| 90–179 days | $121 | $98 | +24% | 25 |
| 180+ days | $152 | $138 | +55% | 25 |
Could a nearby airport be cheaper?
A different airport at either end can change the fare — sometimes a lot.
Return
Philadelphia → Chicago
130 km from New York
$255
$1 more than flying from New York
1 Nov – 6 Nov · PHL → ORD · out 1 stop, back nonstop
found today
Newburgh → Chicago
88 km from New York
$427
$173 more than flying from New York
1 Nov – 6 Nov · SWF → ORD · out 1 stop, back 1 stop
found today
New Haven → Chicago
112 km from New York
$516
$262 more than flying from New York
22 Oct – 25 Oct · HVN → ORD · out 1 stop, back 2 stops
found 6 days ago
Cheapest recent price on each route — round trip, per traveler in Economy. Distances are in a straight line.
One-way
Philadelphia → Chicago
130 km from New York
$135
$29 less than flying from New York
31 Oct · PHL → ORD · 1 stop
found 4 days ago
Islip → Chicago
77 km from New York
$160
$4 less than flying from New York
13 Dec · ISP → ORD · 1 stop
found 5 days ago
Westchester County → Chicago
41 km from New York
$296
$132 more than flying from New York
28 Oct · HPN → RFD · 2 stops
found yesterday
Newburgh → Chicago
88 km from New York
$382
$218 more than flying from New York
29 Mar 2027 · SWF → MDW · 1 stop
found 2 days ago
Cheapest recent price on each route — one way, per traveler in Economy. Distances are in a straight line.
Live price for these dates
The cheapest return found recently is for 4 Dec – 6 Dec. A live search on this page shows what those dates cost now, for one adult in economy.
Prices are what travelers' searches on Aviasales found in the last 7 days, in US dollars: the price the seller showed on Aviasales; bags may cost extra. Fares change, so check today's price before you book. How our prices work