Cheap Flights from Denver to Chicago
Browse current best options from Denver. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Denver
RatePunk searches hundreds of travel sites at once for deals on flights to Chicago
Prices updated 24 days ago
486,190 searches this week
171 airlines compared
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Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)
Today’s best flight deals from Denver to Chicago
Explore current cheapest deals departing from Denver to Chicago
Round trip
Sort by: Cheapest
October 30 - November 17
DEN - Chicago
$137
$82
Round trip
October 23 - October 28
DEN - Chicago
$153
$82
Round trip
October 23 - November 17
DEN - Chicago
$129
$82
Round trip
November 13 - November 17
DEN - Chicago
$148
$82
Round trip
October 2 - October 21
DEN - Chicago
$119
$82
Round trip
October 2 - October 28
DEN - Chicago
$118
$82
Round trip
October 2 - October 20
DEN - Chicago
$119
$82
Round trip
September 15 - September 18
DEN - Chicago
$150
$83
Round trip
September 15 - October 2
DEN - Chicago
$126
$83
Round trip
September 30 - October 20
DEN - Chicago
$140
$83
Round trip
Unlock all 500+ flight deals to Chicago and get alerts when great deals appear
Route Intelligence — 486,190 Searches this Week
Insights for flights from Denver to Chicago
How much is a round trip from Denver to Chicago
Regular price: $101 - $223
Prices are currently below the regular range.
The regular price range for flights from Denver to Chicago is $101 to $223. The current lowest deal is $82 with Frontier Airlines, for travel from Oct 23 to Nov 17.
now $82
Low $101
High $223
The cheapest time to fly from Denver to Chicago
The cheapest month to fly from Denver to Chicago is August, with a median price of $103. The most expensive month is February, with a median price of $340. Prices are generally lower from March to December.
August
Flights from $103
February
Flights from $340
Direct flights from Denver to Chicago
Frontier Airlines
Last-minute flights going from Denver to Chicago
Tue, Jun 16
DEN - Chicago
Denver (DEN) - Chicago (MDW)
Frontier Airlines
$462
$228
One-way
Wed, Jun 17
DEN - Chicago
Denver (DEN) - Chicago (MDW)
Frontier Airlines
$455
$228
One-way
Wed, Jun 17
DEN - Chicago
Denver (DEN) - Chicago (MDW)
Frontier Airlines
$462
$282
One-way
Wed, Jun 17
DEN - Chicago
Denver (DEN) - Chicago (MDW)
Frontier Airlines
$460
$282
One-way
Tue, Jun 23
DEN - Chicago
Denver (DEN) - Chicago (MDW)
Frontier Airlines
$385
$243
One-way
Wed, Jun 24
DEN - Chicago
Denver (DEN) - Chicago (MDW)
Frontier Airlines
$372
$257
One-way
Biggest price drops on these dates for flights from Denver to Chicago
Jun 16 - Jun 17
$462 → $228
51%
Jun 17 - Jun 20
$455 → $228
50%
Jun 17 - Jun 18
$462 → $282
39%
Jun 17 - Jun 19
$460 → $282
39%
Popular Airports to fly from Denver to Chicago
Denver - Chicago route insights
💸 Price insights
Recent fares are above the typical level
Recent fares from Denver to Chicago are above the typical level for this route.
📅 Best time to fly
August is historically the cheapest month to fly
Historically, August is the cheapest month to fly from Denver to Chicago, with a median price of $103.
⏱️ Flight duration
Direct flights average 5h 40m
Direct flights from Denver to Chicago typically take 5 hours and 40 minutes.
✈️ Airlines & availability
Frontier Airlines offers direct flights
Frontier Airlines offers direct flights on the Denver to Chicago route.
🏆 Airline highlight
Frontier Airlines has a recent deal for $82
Frontier Airlines recently offered a deal for $82 from Denver to Chicago.
🎯 Booking tip
Deals are frequent for this route
Deals for flights from Denver to Chicago are frequent, appearing over once per day.
Denver main airports to depart from
Denver International (DEN)
Denver International Airport is a great choice for flights from Denver to Chicago.
📍 ~33 km from city center (reachable by car or train)
💸 Flights from ~$82
Chicago main airports to arrive at
O Hare International (ORD)
O'Hare International Airport is a major hub for flights to Chicago from Denver, offering many options.
📍 ~25 km from Chicago city center (reachable by car, train, and bus).
💸 Flights from ~$82
Chicago Midway International (MDW)
Chicago Midway International Airport is a convenient option for flights to Chicago from Denver.
📍 ~15 km from Chicago city center (reachable by car, train, and bus).
💸 Flights from ~$160
Chicago Rockford International (RFD)
Chicago Rockford International Airport serves the wider Chicago area for flights from Denver.
📍 ~120 km from Chicago city center (reachable by car).
💸 Flights from ~$248
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
General Mitchell International offers excellent proximity to Chicago with high-frequency flight options and direct rail access.
📍 ~135 km from Chicago (reachable by car, train)
💸 Flights from ~$226
South Bend International (SBN)
South Bend International is geographically the closest alternative to the Chicago area, with direct commuter rail access.
📍 ~120 km from Chicago (reachable by car, train)
💸 Flights from ~$225
Gerald R. Ford International (GRR)
Gerald R. Ford International is a major regional hub, offering a wide range of cabin classes for travelers.
📍 ~205 km from Chicago (reachable by car)
💸 Flights from ~$190
Dane County Regional (MSN)
Dane County Regional is a reliable regional airport with consistent service levels and less congestion.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$240
Fort Wayne International (FWA)
Fort Wayne International provides stable regional service for travelers in the southeastern Chicago suburbs.
📍 ~235 km from Chicago (reachable by car)
💸 Flights from ~$285
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from Denver to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From DEN
Elite
Jun 23
Chicago, United States
81% AI deal score
$1,903
$868
Save $1,035
From DEN
Elite
Aug 04
Chicago, United States
80% AI deal score
$786
$505
Save $281
From DEN
Elite
Aug 04
Chicago, United States
80% AI deal score
$774
$505
Save $269
From DEN
Elite
Aug 11
Chicago, United States
79% AI deal score
$760
$505
Save $255
From DEN
Elite
Aug 26
Chicago, United States
79% AI deal score
$756
$505
Save $251
From DEN
Elite
Nov 11
Chicago, United States
78% AI deal score
$723
$505
Save $218
From DEN
Elite
Nov 04
Chicago, United States
78% AI deal score
$724
$505
Save $219
From DEN
Elite
Jul 14
Chicago, United States
78% AI deal score
$686
$505
Save $181
From DEN
Elite
Jul 08
Chicago, United States
78% AI deal score
$712
$505
Save $207
From DEN
Elite
Jul 21
Chicago, United States
78% AI deal score
$690
$505
Save $185
From DEN
Elite
Jul 22
Chicago, United States
78% AI deal score
$676
$505
Save $171
From DEN
Elite
Dec 01
Chicago, United States
78% AI deal score
$728
$505
Save $223
From DEN
Elite
Oct 28
Chicago, United States
77% AI deal score
$708
$505
Save $203
From DEN
Elite
Oct 13
Chicago, United States
77% AI deal score
$700
$505
Save $195
From DEN
Elite
Oct 20
Chicago, United States
77% AI deal score
$706
$505
Save $201
From DEN
Elite
Nov 16
Chicago, United States
77% AI deal score
$723
$527
Save $196
From DEN
Elite
Jul 08
Chicago, United States
77% AI deal score
$1,551
$667
Save $884
From DEN
Elite
Aug 12
Chicago, United States
77% AI deal score
$1,362
$742
Save $620
From DEN
Elite
Aug 18
Chicago, United States
76% AI deal score
$2,249
$1,330
Save $919
From DEN
Elite
Aug 17
Chicago, United States
76% AI deal score
$2,257
$1,347
Save $910
From DEN
Elite
Aug 31
Chicago, United States
76% AI deal score
$2,282
$1,351
Save $931
From DEN
Elite
Aug 04
Chicago, United States
76% AI deal score
$2,491
$1,438
Save $1,053
From DEN
Elite
Sep 16
Chicago, United States
76% AI deal score
$662
$505
Save $157
From DEN
Elite
Sep 15
Chicago, United States
76% AI deal score
$662
$505
Save $157
From DEN
Elite
Nov 14
Chicago, United States
76% AI deal score
$723
$546
Save $177
From DEN
Elite
Jul 07
Chicago, United States
76% AI deal score
$1,215
$565
Save $650
From DEN
Elite
Aug 11
Chicago, United States
76% AI deal score
$773
$533
Save $240
From DEN
Elite
Aug 24
Chicago, United States
75% AI deal score
$2,239
$1,351
Save $888
From DEN
Elite
Jul 15
Chicago, United States
75% AI deal score
$687
$505
Save $182
From DEN
Elite
Jun 27
Chicago, United States
75% AI deal score
$1,574
$984
Save $590
From DEN
Elite
Aug 13
Chicago, United States
75% AI deal score
$771
$544
Save $227
From DEN
Elite
Aug 12
Chicago, United States
75% AI deal score
$769
$544
Save $225
From DEN
Elite
Aug 20
Chicago, United States
75% AI deal score
$814
$555
Save $259
From DEN
Elite
Aug 10
Chicago, United States
75% AI deal score
$799
$555
Save $244
From DEN
Elite
Aug 08
Chicago, United States
75% AI deal score
$808
$555
Save $253
From DEN
Elite
Jul 15
Chicago, United States
74% AI deal score
$725
$535
Save $190
From DEN
Elite
Aug 23
Chicago, United States
74% AI deal score
$806
$565
Save $241
From DEN
Elite
Sep 26
Chicago, United States
74% AI deal score
$990
$673
Save $317
From DEN
Elite
Jul 23
Chicago, United States
73% AI deal score
$737
$565
Save $172
From DEN
Elite
Oct 05
Chicago, United States
73% AI deal score
$939
$646
Save $293
From DEN
Elite
Aug 19
Chicago, United States
72% AI deal score
$1,760
$1,179
Save $581
From DEN
Elite
Sep 01
Chicago, United States
71% AI deal score
$2,096
$1,329
Save $767
From DEN
Elite
Sep 08
Chicago, United States
71% AI deal score
$2,139
$1,329
Save $810
From DEN
Elite
Sep 07
Chicago, United States
71% AI deal score
$2,135
$1,351
Save $784
From DEN
Elite
Sep 14
Chicago, United States
71% AI deal score
$2,277
$1,360
Save $917
From DEN
Elite
Aug 25
Chicago, United States
71% AI deal score
$2,239
$1,385
Save $854
From DEN
Elite
Aug 12
Chicago, United States
71% AI deal score
$792
$563
Save $229
From DEN
Elite
Sep 08
Chicago, United States
70% AI deal score
$717
$533
Save $184
From DEN
Elite
Sep 01
Chicago, United States
70% AI deal score
$706
$544
Save $162
From DEN
Elite
Sep 28
Chicago, United States
70% AI deal score
$718
$544
Save $174
From DEN
Elite
Oct 12
Chicago, United States
70% AI deal score
$723
$555
Save $168
From DEN
Elite
Oct 15
Chicago, United States
70% AI deal score
$731
$555
Save $176
From DEN
Elite
Sep 11
Chicago, United States
69% AI deal score
$759
$593
Save $166
From DEN
Elite
Jun 16
Chicago, United States
68% AI deal score
$2,429
$2,026
Save $403
From DEN
Elite
Nov 17
Chicago, United States
67% AI deal score
$723
$667
Save $56
From DEN
Elite
Jul 03
Chicago, United States
67% AI deal score
$1,670
$1,227
Save $443
From DEN
Elite
Aug 05
Chicago, United States
67% AI deal score
$1,917
$1,356
Save $561
From DEN
Elite
Aug 05
Chicago, United States
67% AI deal score
$1,960
$1,406
Save $554
From DEN
Elite
Jul 07
Chicago, United States
67% AI deal score
$619
$533
Save $86
From DEN
Elite
Jul 08
Chicago, United States
67% AI deal score
$619
$533
Save $86
From DEN
Elite
Jul 07
Chicago, United States
66% AI deal score
$1,164
$908
Save $256
From DEN
Elite
Jul 03
Chicago, United States
66% AI deal score
$1,597
$1,227
Save $370
From DEN
Elite
Jun 19
Chicago, United States
66% AI deal score
$2,073
$1,514
Save $559
From DEN
Elite
Jun 19
Chicago, United States
66% AI deal score
$2,149
$1,619
Save $530
From DEN
Elite
Jun 18
Chicago, United States
66% AI deal score
$2,231
$1,696
Save $535
From DEN
Elite
Sep 26
Chicago, United States
66% AI deal score
$719
$574
Save $145
From DEN
Elite
Oct 05
Chicago, United States
66% AI deal score
$727
$574
Save $153
From DEN
Elite
Jun 30
Chicago, United States
65% AI deal score
$1,499
$1,227
Save $272
From DEN
Elite
Jul 03
Chicago, United States
65% AI deal score
$1,709
$1,357
Save $352
From DEN
Elite
Sep 10
Chicago, United States
49% AI deal score
$1,386
$1,190
Save $196
From DEN
Elite
Aug 01
Chicago, United States
49% AI deal score
$1,442
$1,209
Save $233
From DEN
Elite
Jul 18
Chicago, United States
49% AI deal score
$1,636
$1,374
Save $262
From DEN
Elite
Sep 05
Chicago, United States
48% AI deal score
$1,366
$1,195
Save $171
From DEN
Elite
Jul 01
Chicago, United States
48% AI deal score
$1,619
$1,417
Save $202
From DEN
Elite
Aug 06
Chicago, United States
47% AI deal score
$1,356
$1,210
Save $146
From DEN
Elite
Jul 12
Chicago, United States
47% AI deal score
$1,636
$1,482
Save $154
From DEN
Elite
Jun 25
Chicago, United States
47% AI deal score
$1,948
$1,789
Save $159
From DEN
Elite
Jul 07
Chicago, United States
47% AI deal score
$621
$593
Save $28
From DEN
Elite
Jul 07
Chicago, United States
47% AI deal score
$619
$593
Save $26
From DEN
Elite
Jul 08
Chicago, United States
47% AI deal score
$620
$593
Save $27
From DEN
Elite
Jul 01
Chicago, United States
46% AI deal score
$1,423
$1,366
Save $57
From DEN
Elite
Jul 02
Chicago, United States
46% AI deal score
$1,670
$1,612
Save $58
From DEN
Elite
Jun 22
Chicago, United States
46% AI deal score
$2,006
$1,916
Save $90
From DEN
Elite
Aug 13
Chicago, United States
45% AI deal score
$1,346
$1,316
Save $30
From DEN
Elite
Jun 30
Chicago, United States
45% AI deal score
$1,430
$1,396
Save $34
From DEN
Elite
Jul 08
Chicago, United States
45% AI deal score
$1,621
$1,602
Save $19
From DEN
Elite
Jul 08
Chicago, United States
44% AI deal score
$710
From DEN
Elite
Jul 26
Chicago, United States
44% AI deal score
$760
From DEN
Elite
Aug 02
Chicago, United States
40% AI deal score
$1,420
From DEN
Elite
Jun 23
Chicago, United States
40% AI deal score
$1,733
From DEN
Elite
Jun 17
Chicago, United States
39% AI deal score
$1,509
From DEN
Elite
Sep 08
Chicago, United States
38% AI deal score
$12,921
From DEN
Elite
Sep 14
Chicago, United States
38% AI deal score
$12,921
From DEN
Elite
Sep 08
Chicago, United States
38% AI deal score
$12,921
From DEN
Elite
Sep 10
Chicago, United States
38% AI deal score
$12,921
From DEN
Elite
Jul 07
Chicago, United States
38% AI deal score
$1,346
From DEN
Elite
Jun 19
Chicago, United States
38% AI deal score
$2,257
From DEN
Elite
Jul 07
Chicago, United States
37% AI deal score
$1,179
From DEN
Elite
Jul 27
Chicago, United States
37% AI deal score
$1,396
From DEN
Elite
Nov 22
Chicago, United States
37% AI deal score
$1,587