Newburgh to Chicago SWF → MDW, ORD, RFD
Stewart International Airport (SWF) → Chicago Midway International Airport (MDW), O'Hare International Airport (ORD), Chicago Rockford International Airport (RFD)
The cheapest return found recently is $427 with Allegiant Air, 1 Nov – 6 Nov, found today. The cheapest one-way found recently is $382 with Allegiant Air, 29 Mar 2027, found 2 days ago.
Return
The cheapest return fare on each of 3 departure dates is usually $274 to $360.
Cheapest return found recently
$427
1 Nov – 6 Nov · Allegiant Air
Stewart International Airport (SWF) → O'Hare International Airport (ORD)
Leaves 11:58 a.m. · Return leaves 7:49 p.m. · 40 h 24 min of travel, both ways together
out 1 stop, back 1 stop
found today
Cheapest nonstop return
None seen yet.
Found recently, and the cheapest we hold
$427 1 Nov – 6 Novfound todaySee prices for these dates
$256 10 Dec – 14 Decfound 6 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 $256 to $540.
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 3 departure dates from 1 Nov to 28 Jan 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 5-night return fares leaving within 3 days of 1 Nov to compare.
Every date we hold
3 fares on 3 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 1 Nov – 6 Nov | $427 | Allegiant Air | Stewart International Airport (SWF) → O'Hare International Airport (ORD) | out 1 stop, back 1 stop | found today | See prices for these dates |
| 10 Dec – 14 Dec | $256 | Allegiant Air | Stewart International Airport (SWF) → O'Hare International Airport (ORD) | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| 28 Jan 2027 – 1 Feb 2027 | $292 | Allegiant Air | Stewart International Airport (SWF) → O'Hare International Airport (ORD) | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
Which month looks cheapest?
December 2026 is the cheapest month — from $256.
Airlines on the cheapest dates: Allegiant Air.
One-way
The cheapest one-way fare on each of 7 departure dates is usually $225 to $341.
Cheapest one-way found recently
$382
29 Mar 2027 · Allegiant Air
Stewart International Airport (SWF) → Chicago Midway International Airport (MDW)
Leaves 7:52 p.m. · 24 h 50 min trip
1 stop
found 2 days ago
Cheapest nonstop one-way
None seen yet.
Found recently, and the cheapest we hold
$382 29 Mar 2027found 2 days agoOpen this trip
$187 12 Decfound 6 days agoOpen this trip
What have prices looked like?
Over 22 days, 24 Sept to 18 Oct, the cheapest one-way we saw each day was $157 to $339.
At $382, the cheapest one-way found recently is above that range.
22 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 7 departure dates from 12 Dec to 12 Apr 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 29 Mar 2027 to compare.
Every date we hold
7 fares on 7 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 12 Dec | $187 | Breeze Airways | Stewart International Airport (SWF) → O'Hare International Airport (ORD) | 2 stops | found 6 days ago | Open this trip |
| 29 Dec | $335 | Allegiant Air | Stewart International Airport (SWF) → O'Hare International Airport (ORD) | 1 stop | found 5 days ago | Open this trip |
| 7 Jan 2027 | $228 | Allegiant Air | Stewart International Airport (SWF) → Chicago Rockford International Airport (RFD) | 1 stop | found 5 days ago | Open this trip |
| 5 Feb 2027 | $221 | Allegiant Air | Stewart International Airport (SWF) → Chicago Rockford International Airport (RFD) | 1 stop | found 3 days ago | Open this trip |
| 29 Mar 2027 | $382 | Allegiant Air | Stewart International Airport (SWF) → Chicago Midway International Airport (MDW) | 1 stop | found 2 days ago | Open this trip |
| 3 Apr 2027 | $324 | Allegiant Air | Stewart International Airport (SWF) → O'Hare International Airport (ORD) | 1 stop | found 3 days ago | Open this trip |
| 12 Apr 2027 | $346 | Allegiant Air | Stewart International Airport (SWF) → Chicago Rockford International Airport (RFD) | 1 stop | found 5 days ago | Open this trip |
Which month looks cheapest?
December 2026 is the cheapest month — from $187.
Airlines on the cheapest dates: Allegiant Air, Breeze Airways.
Premium cabin fares from Newburgh to Chicago
We hold no premium economy, business or first-class fares for this route: we collect them for the busiest routes, and this one is not among them yet.
Today's prices for 1 Nov – 6 Nov in another cabin: Premium economy · Business · First
Today's prices for 29 Mar 2027 in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for Newburgh to Chicago?
Return
Fares 30 to 59 days before departure were typically 7% lower than 14 to 29 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 |
|---|---|---|---|---|
| 14–29 days | $340 | $334 | +7% | 11 |
| 30–59 days | $317 | $256 | Cheapest seen | 18 |
| 60–89 days | $499 | $340 | +57% | 20 |
| 90–179 days | $366 | $292 | +16% | 21 |
One-way
Fares 90 to 179 days before departure were typically 6% lower than 30 to 59 days before departure.
From the cheapest one-way each day between 24 Sept and 18 Oct (22 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 |
|---|---|---|---|---|
| 30–59 days | $187 | $177 | +7% | 9 |
| 60–89 days | $195 | $157 | +11% | 21 |
| 90–179 days | $175 | $175 | Cheapest seen | 15 |
Could a nearby airport be cheaper?
A different airport at either end can change the fare — sometimes a lot.
Return
New York → Chicago
88 km from Newburgh
$254
$173 less than flying from Newburgh
4 Dec – 6 Dec · EWR → ORD · out nonstop, back nonstop
found yesterday
Hartford → Chicago
127 km from Newburgh
$382
$45 less than flying from Newburgh
29 Oct – 5 Nov · BDL → ORD · out 1 stop, back 1 stop
found today
Albany → Chicago
131 km from Newburgh
$316
$111 less than flying from Newburgh
6 Jan 2027 – 7 Jan 2027 · ALB → ORD · out nonstop, back nonstop
found 2 days ago
New Haven → Chicago
100 km from Newburgh
$516
$89 more than flying from Newburgh
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
Hartford → Chicago
127 km from Newburgh
$133
$249 less than flying from Newburgh
21 Nov · BDL → ORD · 1 stop
found 6 days ago
Islip → Chicago
115 km from Newburgh
$160
$222 less than flying from Newburgh
13 Dec · ISP → ORD · 1 stop
found 5 days ago
New York → Chicago
88 km from Newburgh
$164
$218 less than flying from Newburgh
20 Dec · EWR → ORD · nonstop
found yesterday
Albany → Chicago
131 km from Newburgh
$251
$131 less than flying from Newburgh
27 Oct · ALB → ORD · nonstop
found 2 days ago
Westchester County → Chicago
59 km from Newburgh
$296
$86 less than flying from Newburgh
28 Oct · HPN → RFD · 2 stops
found yesterday
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 1 Nov – 6 Nov. 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