Cheap flights from Denver to Chicago
The cheapest round trip from Denver to Chicago that travelers found recently is $203 with a carry-on: a $93 fare on Frontier plus about $110 for a carry-on both ways. It leaves Thu, Dec 3 and comes back Sat, Dec 5.
Live prices for Thu, Dec 3 to Sat, Dec 5
Cheapest trips travelers found recently
| Leave | Return | Airline | Airports | Stops | Fare | Carry-on (est.) | Total | Live prices |
|---|---|---|---|---|---|---|---|---|
| Thu, Dec 3 | Sat, Dec 5 | Frontier | DEN → ORD | Nonstop | $93 | +$110 | $203 | Live price |
| Fri, Oct 30 | Tue, Nov 3 | Frontier | DEN → ORD | Nonstop | $113 | +$110 | $223 | Live price |
| Fri, Dec 25 | Wed, Dec 30 | Frontier | DEN → ORD | Nonstop | $147 | +$110 | $257 | Live price |
| Sun, Oct 18 | Wed, Oct 21 | Frontier | DEN → ORD | Nonstop | $151 | +$110 | $261 | Live price |
| Sun, Dec 13 | Fri, Dec 18 | Frontier | DEN → ORD | Nonstop | $173 | +$110 | $283 | Live price |
| Sun, Oct 18 | Thu, Oct 22 | Frontier | DEN → ORD | Nonstop | $182 | +$110 | $292 | Live price |
| Fri, Oct 23 | Mon, Oct 26 | Frontier | DEN → ORD | 1 stop | $186 | +$110 | $296 | Live price |
| Sat, Dec 26 | Wed, Dec 30 | Frontier | DEN → ORD | Nonstop | $190 | +$110 | $300 | Live price |
| Thu, Oct 22 | Sun, Oct 25 | Frontier | DEN → ORD | Nonstop | $225 | +$110 | $335 | Live price |
| Fri, Oct 23 | Sun, Oct 25 | Frontier | DEN → ORD | Nonstop | $239 | +$110 | $349 | 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 | Fri, Oct 30 to Tue, Nov 3, 4 nights | $223 | Live price |
| December 2026 | Thu, Dec 3 to Sat, Dec 5, 2 nights | $203 | Live price |
Bag fees on this route
What the airlines flying Denver 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 |
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).
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