Dallas to Chicago DAL, DFW → MDW, ORD
Dallas Love Field (DAL), Dallas/Fort Worth International Airport (DFW) → Chicago Midway International Airport (MDW), O'Hare International Airport (ORD)
The cheapest return found recently is $209 with Frontier Airlines, 5 Nov – 9 Nov, found yesterday. The cheapest one-way found recently is $124 with Contour Airlines, 29 Oct, found yesterday.
Return
The cheapest return fare on each of 5 departure dates is usually $220 to $243.
Cheapest return found recently
$209
5 Nov – 9 Nov · Frontier Airlines
Dallas/Fort Worth International Airport (DFW) → Chicago Midway International Airport (MDW)
Leaves 8:54 a.m. · Return leaves 8:30 p.m. · 5 h 28 min of travel, both ways together
out nonstop, back nonstop
found yesterday
Cheapest nonstop return
$209
5 Nov – 9 Nov · Frontier Airlines
Dallas/Fort Worth International Airport (DFW) → Chicago Midway International Airport (MDW)
Leaves 8:54 a.m. · Return leaves 8:30 p.m. · 5 h 28 min of travel, both ways together
out nonstop, back nonstop
found yesterday
Found recently, and the cheapest we hold
$209 5 Nov – 9 Novfound yesterdaySee prices for these dates
It is also the cheapest return we hold, of any age.
What have prices looked like?
Over 25 days, 24 Sept to 18 Oct, the cheapest return we saw each day was $125 to $269.
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 5 departure dates from 5 Nov to 12 Mar 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 4-night return fares leaving within 3 days of 5 Nov to compare.
Every date we hold
7 fares on 5 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 5 Nov – 9 Nov | $209 | Frontier Airlines | Dallas/Fort Worth International Airport (DFW) → Chicago Midway International Airport (MDW) | out nonstop, back nonstop | found yesterday | See prices for these dates |
| 21 Nov – 23 Nov | $226 | Frontier Airlines | Dallas/Fort Worth International Airport (DFW) → Chicago Midway International Airport (MDW) | out nonstop, back nonstop | found 6 days ago | See prices for these dates |
| 22 Nov – 29 Nov | $243 | Frontier Airlines | Dallas/Fort Worth International Airport (DFW) → O'Hare International Airport (ORD) | out nonstop, back nonstop | found 4 days ago | See prices for these dates |
| 25 Nov – 30 Nov | $220 | Frontier Airlines | Dallas/Fort Worth International Airport (DFW) → Chicago Midway International Airport (MDW) | out nonstop, back nonstop | found 4 days ago | See prices for these dates |
| 12 Mar 2027 – 16 Mar 2027 | $284 | Frontier Airlines | Dallas/Fort Worth International Airport (DFW) → Chicago Midway International Airport (MDW) | out nonstop, back nonstop | found 6 days ago | See prices for these dates |
Which month looks cheapest?
November 2026 is the cheapest month — from $209.
Airlines on the cheapest dates: Frontier Airlines.
One-way
The cheapest one-way fare on each of 4 departure dates is usually $129 to $141.
Cheapest one-way found recently
$124
29 Oct · Contour Airlines
Dallas/Fort Worth International Airport (DFW) → O'Hare International Airport (ORD)
Leaves 9:30 a.m. · 4 h 45 min trip
1 stop
found yesterday
Cheapest nonstop one-way
$142
27 Dec · Frontier Airlines
Dallas/Fort Worth International Airport (DFW) → O'Hare International Airport (ORD)
Leaves 7:02 a.m. · 2 h 35 min trip
nonstop
found 2 days ago
Found recently, and the cheapest we hold
$124 29 Octfound yesterdayOpen this trip
It is also the cheapest one-way we hold, of any age.
What have prices looked like?
Over 25 days, 24 Sept to 18 Oct, the cheapest one-way we saw each day was $80 to $145.
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 4 departure dates from 27 Oct to 27 Dec, 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?
No. We hold one-way fares on 2 other departure dates within 3 days of 29 Oct, and none is cheaper.
Every date we hold
8 fares on 4 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 27 Oct | $135 | Contour Airlines | Dallas/Fort Worth International Airport (DFW) → O'Hare International Airport (ORD) | 1 stop | found 4 days ago | Open this trip |
| 29 Oct | $124 | Contour Airlines | Dallas/Fort Worth International Airport (DFW) → O'Hare International Airport (ORD) | 1 stop | found yesterday | Open this trip |
| 30 Oct | $160 | Frontier Airlines | Dallas/Fort Worth International Airport (DFW) → O'Hare International Airport (ORD) | 1 stop | found 6 days ago | Open this trip |
| 27 Dec | $131 | Frontier Airlines | Dallas/Fort Worth International Airport (DFW) → O'Hare International Airport (ORD) | nonstop | found 6 days ago | Open this trip |
Which month looks cheapest?
October 2026 is the cheapest month — from $124.
Airlines on the cheapest dates: Contour Airlines, Frontier Airlines.
Premium cabin fares from Dallas 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 5 Nov – 9 Nov in another cabin: Premium economy · Business · First
Today's prices for 29 Oct in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for Dallas to Chicago?
Return
Fares 14 to 29 days before departure were typically 28% 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 | $252 | $237 | +39% | 12 |
| 7–13 days | $275 | $188 | +52% | 9 |
| 14–29 days | $181 | $125 | Cheapest seen | 20 |
| 30–59 days | $220 | $145 | +22% | 10 |
| 60–89 days | $211 | $211 | +17% | 14 |
One-way
Fares 60 to 89 days before departure were typically 34% 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 | $154 | $146 | +53% | 9 |
| 7–13 days | $136 | $124 | +35% | 12 |
| 14–29 days | $128 | $124 | +27% | 9 |
| 60–89 days | $101 | $80 | Cheapest seen | 20 |
| 90–179 days | $149 | $138 | +48% | 12 |
| 180+ days | $828 | $539 | +720% | 16 |
Could a nearby airport be cheaper?
A different airport at either end can change the fare — sometimes a lot.
Return
Dallas → Milwaukee
131 km from Chicago
$456
$247 more than flying to Chicago
11 Dec – 14 Dec · DFW → MKE · out nonstop, back nonstop
found yesterday
Cheapest recent price on each route — round trip, per traveler in Economy. Distances are in a straight line.
Live price for these dates
The cheapest return found recently is for 5 Nov – 9 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