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Denver to Chicago DEN → MDW, ORD

Denver International Airport (DEN) → Chicago Midway International Airport (MDW), O'Hare International Airport (ORD)

The cheapest return found recently is $146 with Frontier Airlines, 3 Dec – 5 Dec, found 2 days ago. The cheapest one-way found recently is $84 with Southwest Airlines, 16 Dec, found today.

Return

The cheapest return fare on each of 5 departure dates is usually $192 to $287.

Cheapest return found recently

$146

3 Dec – 5 Dec · Frontier Airlines

Denver International Airport (DEN) → O'Hare International Airport (ORD)

Leaves 9:26 p.m. · Return leaves 7:25 a.m. · 5 h 36 min of travel, both ways together

out nonstop, back nonstop

found 2 days ago

See prices for these datesCheck today's price

Cheapest nonstop return

$146

3 Dec – 5 Dec · Frontier Airlines

Denver International Airport (DEN) → O'Hare International Airport (ORD)

Leaves 9:26 p.m. · Return leaves 7:25 a.m. · 5 h 36 min of travel, both ways together

out nonstop, back nonstop

found 2 days ago

See prices for these datesCheck today's price

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Found recently, and the cheapest we hold

Cheapest found recently $146 3 Dec – 5 Decfound 2 days agoSee prices for these dates

It is also the cheapest return we hold, of any age.

What have prices looked like?

Over 24 days, 25 Sept to 18 Oct, the cheapest return we saw each day was $93 to $311.

$146, the cheapest return found recently, sits here in that range of $93 to $311.

24 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 20 Oct to 28 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?

We hold no other 2-night return fares leaving within 3 days of 3 Dec to compare.

Every date we hold

5 fares on 5 departure dates

20 Oct – 29 Oct: $352, found 3 days ago5 Nov – 8 Nov: $192, found 4 days ago3 Dec – 5 Dec: $146, found 2 days ago27 Dec – 6 Jan 2027: $287, found 4 days ago28 Dec – 7 Jan 2027: $231, found 4 days agoOctNovDec
See the chart as a table
The cheapest price seen for each departure date — per traveler in Economy.
DatesFromAirlineAirportsStopsFound
20 Oct – 29 Oct$352Frontier AirlinesDenver International Airport (DEN) → O'Hare International Airport (ORD)out nonstop, back nonstopfound 3 days agoSee prices for these dates
5 Nov – 8 Nov$192Frontier AirlinesDenver International Airport (DEN) → O'Hare International Airport (ORD)out nonstop, back nonstopfound 4 days agoSee prices for these dates
3 Dec – 5 Dec$146Frontier AirlinesDenver International Airport (DEN) → O'Hare International Airport (ORD)out nonstop, back nonstopfound 2 days agoSee prices for these dates
27 Dec – 6 Jan 2027$287Southwest AirlinesDenver International Airport (DEN) → Chicago Midway International Airport (MDW)out nonstop, back nonstopfound 4 days agoSee prices for these dates
28 Dec – 7 Jan 2027$231Frontier AirlinesDenver International Airport (DEN) → O'Hare International Airport (ORD)out nonstop, back nonstopfound 4 days agoSee prices for these dates

Which month looks cheapest?

December 2026 is the cheapest month — from $146.

October 2026From $3521 departure date20 Oct – 29 Oct · found 3 days agoSee prices for these dates
November 2026From $1921 departure date5 Nov – 8 Nov · found 4 days agoSee prices for these dates
December 2026From $146Cheapest seen3 departure dates3 Dec – 5 Dec · found 2 days agoSee prices for these dates

Airlines on the cheapest dates: Frontier Airlines, Southwest Airlines.

One-way

The cheapest one-way fare on each of 5 departure dates is usually $80 to $126.

Cheapest one-way found recently

$84

16 Dec · Southwest Airlines

Denver International Airport (DEN) → Chicago Midway International Airport (MDW)

Leaves 2:10 p.m. · 2 h 20 min trip

nonstop

found today

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Cheapest nonstop one-way

$84

16 Dec · Southwest Airlines

Denver International Airport (DEN) → Chicago Midway International Airport (MDW)

Leaves 2:10 p.m. · 2 h 20 min trip

nonstop

found today

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Found recently, and the cheapest we hold

Cheapest found recently $84 16 Decfound todayOpen this trip

Cheapest we hold, of any age $76 14 Decfound 3 days agoOpen this trip

What have prices looked like?

Over 25 days, 24 Sept to 18 Oct, the cheapest one-way we saw each day was $71 to $158.

$84, the cheapest one-way found recently, sits here in that range of $71 to $158.

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 5 departure dates from 24 Oct to 16 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?

Yes. Among one-way fares leaving within 3 days of 16 Dec, 14 Dec costs $76: $8 less than the cheapest found recently.

Frontier Airlines · Denver International Airport (DEN) → O'Hare International Airport (ORD) · nonstop · found 3 days ago

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Every date we hold

6 fares on 5 departure dates

24 Oct: $141, found 3 days ago20 Nov: $126, found today30 Nov: $125, found today14 Dec: $76, found 3 days ago16 Dec: $80, found 6 days agoOctNovDec
See the chart as a table
The cheapest price seen for each departure date — per traveler in Economy.
DatesFromAirlineAirportsStopsFound
24 Oct$141Frontier AirlinesDenver International Airport (DEN) → O'Hare International Airport (ORD)1 stopfound 3 days agoOpen this trip
20 Nov$126Frontier AirlinesDenver International Airport (DEN) → O'Hare International Airport (ORD)1 stopfound todayOpen this trip
30 Nov$125Southwest AirlinesDenver International Airport (DEN) → Chicago Midway International Airport (MDW)nonstopfound todayOpen this trip
14 Dec$76Frontier AirlinesDenver International Airport (DEN) → O'Hare International Airport (ORD)nonstopfound 3 days agoOpen this trip
16 Dec$80Frontier AirlinesDenver International Airport (DEN) → O'Hare International Airport (ORD)nonstopfound 6 days agoOpen this trip

Which month looks cheapest?

December 2026 is the cheapest month — from $76.

October 2026From $1411 departure date24 Oct · found 3 days agoOpen this trip
November 2026From $1252 departure dates30 Nov · found todayOpen this trip
December 2026From $76Cheapest seen2 departure dates14 Dec · found 3 days agoOpen this trip

Airlines on the cheapest dates: Frontier Airlines, Southwest Airlines.

Premium cabin fares from Denver 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 3 Dec – 5 Dec in another cabin: Premium economy · Business · First

Today's prices for 16 Dec in another cabin: Premium economy · Business · First

How far ahead were prices cheapest for Denver to Chicago?

Return

Fares 30 to 59 days before departure were typically 55% lower than 7 to 13 days before departure.

From the cheapest return each day between 25 Sept and 18 Oct (24 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
Typical price in each booking range — round trip, per traveler in Economy.
Booked ahead byTypical fareCheapest dayAbove the cheapestDays of prices
7–13 days$206$186+121%12
14–29 days$186$113+100%20
30–59 days$93$93Cheapest seen9
60–89 days$147$147+58%10
90–179 days$311$311+234%8
180+ days$301$301+224%8

One-way

Fares 14 to 29 days before departure were typically 53% 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
Typical price in each booking range — one way, per traveler in Economy.
Booked ahead byTypical fareCheapest dayAbove the cheapestDays of prices
0–6 days$158$141+114%14
7–13 days$158$145+114%8
14–29 days$74$71Cheapest seen14
30–59 days$118$76+60%11
60–89 days$84$80+14%13

Could a nearby airport be cheaper?

A different airport at either end can change the fare — sometimes a lot.

One-way

Colorado Springs → Chicago

102 km from Denver

$257

$173 more than flying from Denver

28 Oct · COS → ORD · nonstop

found yesterday

See this route

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 3 Dec – 5 Dec. 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