Cheap flights from Chicago to Newburgh from $183 MDW, RFD → SWF
Chicago Midway International Airport (MDW), Chicago Rockford International Airport (RFD) → Stewart International Airport (SWF)
The cheapest return found recently is $1,004 with Allegiant Air, 18 Dec – 20 Dec, found 5 days ago. The cheapest one-way found recently is $183 with Allegiant Air, 7 Feb 2027, found 4 days ago.
- Cheapest one-way found recently
- $183, found 4 days ago
- Cheapest return found recently
- $1,004, 18 Dec to 20 Dec
- Cheapest month to fly
- March 2027, return fares from $554 found in the last 7 days
Return
Not enough comparable prices yet for a usual return price.
Cheapest return found recently
$1,004
18 Dec – 20 Dec · Allegiant Air
Chicago Rockford International Airport (RFD) → Stewart International Airport (SWF)
Leaves 9:50 a.m. · Return leaves 5:30 p.m. · 24 h 5 min of travel, both ways together
out 1 stop, back 1 stop
found 5 days ago
Cheapest nonstop return
None seen yet.
Found recently, and the cheapest we hold
$1,004 18 Dec – 20 Decfound 5 days agoSee prices for these dates
$554 11 Mar 2027 – 13 Mar 2027found 6 days agoSee prices for these dates
What have prices looked like?
Over 30 days, 28 Sept to 11 Nov, the cheapest return we saw each day was $443 to $798.
At $1,004, the cheapest return found recently is above that range.
Those were the prices on those days, not today's.
Is this a good return price?
Not enough comparable prices yet: we hold return fares on 2 departure dates and need at least 3 to say what is usual.
Could nearby dates be cheaper?
We hold no other 2-night return fares leaving within 3 days of 18 Dec to compare.
Every date we hold
2 fares on 2 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 18 Dec – 20 Dec | $1,004 | Allegiant Air | Chicago Rockford International Airport (RFD) → Stewart International Airport (SWF) | out 1 stop, back 1 stop | found 5 days ago | See prices for these dates |
| 11 Mar 2027 – 13 Mar 2027 | $554 | Frontier Airlines | Chicago Midway International Airport (MDW) → Stewart International Airport (SWF) | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
Which month looks cheapest?
March 2027 is the cheapest month — from $554.
Airlines on the cheapest dates: Allegiant Air, Frontier Airlines.
One-way
The cheapest one-way fare on each of 5 departure dates is usually $212 to $293.
Cheapest one-way found recently
$183
7 Feb 2027 · Allegiant Air
Chicago Rockford International Airport (RFD) → Stewart International Airport (SWF)
Leaves 6:01 p.m. · 15 h 10 min trip
1 stop
found 4 days ago
Cheapest nonstop one-way
None seen yet.
Found recently, and the cheapest we hold
$183 7 Feb 2027found 4 days agoOpen this trip
It is also the cheapest one-way we hold, of any age.
What have prices looked like?
Over 49 days, 24 Sept to 11 Nov, the cheapest one-way we saw each day was $183 to $479.
At $183, the cheapest one-way found recently is at the low end of that range.
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 5 departure dates from 6 Dec to 7 May 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 7 Feb 2027 to compare.
Every date we hold
5 fares on 5 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 6 Dec | $212 | Allegiant Air | Chicago Rockford International Airport (RFD) → Stewart International Airport (SWF) | 1 stop | found 4 days ago | Open this trip |
| 31 Dec | $356 | Allegiant Air | Chicago Rockford International Airport (RFD) → Stewart International Airport (SWF) | 1 stop | found 7 days ago | Open this trip |
| 7 Feb 2027 | $183 | Allegiant Air | Chicago Rockford International Airport (RFD) → Stewart International Airport (SWF) | 1 stop | found 4 days ago | Open this trip |
| 3 Mar 2027 | $247 | Allegiant Air | Chicago Rockford International Airport (RFD) → Stewart International Airport (SWF) | 1 stop | found 6 days ago | Open this trip |
| 7 May 2027 | $293 | Allegiant Air | Chicago Rockford International Airport (RFD) → Stewart International Airport (SWF) | 1 stop | found 4 days ago | Open this trip |
Which month looks cheapest?
February 2027 is the cheapest month — from $183.
Airlines on the cheapest dates: Allegiant Air.
Premium cabin fares from Chicago to Newburgh
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 18 Dec – 20 Dec in another cabin: Premium economy · Business · First
Today's prices for 7 Feb 2027 in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for Chicago to Newburgh?
Return
Not enough history yet: in 30 days of return prices, 28 Sept to 11 Nov, fewer than 3 booking ranges had prices on 7 days or more.
One-way
Fares 180 or more days before departure were typically 13% lower than 14 to 29 days before departure.
From the cheapest one-way each day between 24 Sept and 11 Nov (49 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 | $291 | $209 | +15% | 15 |
| 30–59 days | $310 | $209 | +23% | 18 |
| 60–89 days | $345 | $183 | +36% | 21 |
| 90–179 days | $278 | $183 | +10% | 18 |
| 180+ days | $253 | $235 | Cheapest seen | 24 |
Could a nearby airport be cheaper?
A different airport at either end can change the fare — sometimes a lot.
Return
Chicago → New York
88 km from Newburgh
$195
$809 less than flying to Newburgh
3 Feb 2027 – 9 Feb 2027 · MDW → LGA · out 1 stop, back 1 stop
found yesterday
Cheapest recent price on each route — round trip, per traveler in Economy. Distances are in a straight line.
One-way
Chicago → New York
88 km from Newburgh
$96
$87 less than flying to Newburgh
19 Nov · ORD → LGA · stops unknown
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 18 Dec – 20 Dec. A live search on this page shows what those dates cost now, for one adult in economy.
Questions about this trip
How much is a return flight from Chicago to Newburgh?
The cheapest return found recently is $1,004 with Allegiant Air, 18 Dec to 20 Dec, found 5 days ago. The cheapest return we hold, of any age, is $554 with Frontier Airlines, 11 Mar 2027 to 13 Mar 2027, found 6 days ago.
How much is a one-way flight from Chicago to Newburgh?
The cheapest one-way found recently is $183 with Allegiant Air, 7 Feb 2027, found 4 days ago. The cheapest one-way fare on each of 5 departure dates is usually $212 to $293.
What is the cheapest month to fly from Chicago to Newburgh?
March 2027 is the cheapest month for a return, from $554, 11 Mar 2027 to 13 Mar 2027, found 6 days ago. February 2027 is the cheapest month for a one-way, from $183, 7 Feb 2027, found 4 days ago.
How far ahead should I book a flight from Chicago to Newburgh?
In 49 days of prices between 24 Sept and 11 Nov, one-way fares 180 or more days before departure were typically 13% lower than 14 to 29 days before departure.
How long is the flight from Chicago to Newburgh?
The cheapest one-way found recently, with Allegiant Air on 7 Feb 2027, takes 15 h 10 min with 1 stop.
Which airlines have the cheapest flights from Chicago to Newburgh?
Between 6 Dec and 7 May 2027, Allegiant Air has the cheapest one-way on all 5 departure dates we hold.
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