Cheap flights from Dallas to Chicago
The cheapest round trip from Dallas to Chicago that travelers found recently is $235 with a carry-on: a $125 fare on Frontier plus about $110 for a carry-on both ways. It leaves Thu, Nov 5 and comes back Tue, Nov 10.
Live prices for Thu, Nov 5 to Tue, Nov 10
Cheapest trips travelers found recently
| Leave | Return | Airline | Airports | Stops | Fare | Carry-on (est.) | Total | Live prices |
|---|---|---|---|---|---|---|---|---|
| Thu, Nov 5 | Tue, Nov 10 | Frontier | DFW → MDW | 1 stop | $125 | +$110 | $235 | Live price |
| Wed, Oct 28 | Sat, Oct 31 | Frontier | DFW → ORD | 1 stop | $196 | +$110 | $306 | Live price |
| Sat, Nov 21 | Mon, Nov 23 | Frontier | DFW → MDW | Nonstop | $226 | +$110 | $336 | Live price |
| Fri, Nov 13 | Sun, Nov 15 | Frontier | DFW → ORD | Nonstop | $227 | +$110 | $337 | Live price |
| Fri, Oct 16 | Mon, Oct 19 | LF | DFW → ORD | 1 stop | $348 | Included | $348 | Live price |
| Thu, Oct 29 | Sun, Nov 1 | Frontier | DFW → MDW | 1 stop | $261 | +$110 | $371 | Live price |
| Wed, Nov 25 | Sun, Nov 29 | Frontier | DFW → MDW | 1 stop | $274 | +$110 | $384 | Live price |
| Fri, Mar 12 | Tue, Mar 16 | Frontier | DFW → MDW | Nonstop | $284 | +$110 | $394 | Live price |
Round-trip prices per person, from real fares travelers found in the last few days. Carry-on fees are our estimate for each airline, both ways. Prices change fast: check the live price before you book.
Cheapest month to fly
| Month | Cheapest trip | From | Live prices |
|---|---|---|---|
| October 2026 | Wed, Oct 28 to Sat, Oct 31, 3 nights | $306 | Live price |
| November 2026 | Thu, Nov 5 to Tue, Nov 10, 5 nights | $235 | Live price |
| March 2027 | Fri, Mar 12 to Tue, Mar 16, 4 nights | $394 | Live price |
Bag fees on this route
What the airlines flying Dallas to Chicago usually charge for one bag each way. Budget airlines often sell the cheapest fares and charge the most for bags, so compare the total, not the fare.
| Airline | Carry-on, each way | Checked bag, each way |
|---|---|---|
| Frontier | $55 | $50 |
| LF | Included | $40 |
Our estimates: fees depend on the fare type and when you pay. Check the airline's own price when you book.
How these prices work
These are real round-trip fares that travelers found on Aviasales recently, not a live search, so they can change or sell out. Dipt adds an estimate of each airline's carry-on fee, so a cheap fare with expensive bags doesn't look cheaper than it is. "Live price" opens Dipt's live flight search for those dates, where you book with the airline or travel site you pick. Dipt may earn a commission when you book, at no extra cost to you (how Dipt makes money).
Not sure where to go? Tell Dipt your budget and vibe and it finds the trip.
More cheap flights from Dallas
- Dallas to Amsterdam
- Dallas to Athens
- Dallas to Atlanta
- Dallas to Bali
- Dallas to Bangkok
- Dallas to Barcelona
- Dallas to Berlin
- Dallas to Boston
- Dallas to Cancún
- Dallas to Cartagena
- Dallas to Denver
- Dallas to Dublin
- Dallas to Honolulu
- Dallas to Las Vegas
- Dallas to Lisbon
- Dallas to London
- Dallas to Los Angeles
- Dallas to Medellín
- Dallas to Mexico City
- Dallas to Miami
- Dallas to Montréal
- Dallas to Nashville
- Dallas to New Orleans
- Dallas to New York
- Dallas to Paris
- Dallas to Reykjavík
- Dallas to San Diego
- Dallas to San Francisco
- Dallas to San Juan
- Dallas to Seattle
- Dallas to Seoul
- Dallas to Tokyo
- Dallas to Toronto