Cheap Flights from Detroit to Chicago
Browse current best options from Detroit. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Detroit
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Prices updated 24 days ago
486,190 searches this week
171 airlines compared
80%+ AI score for best value
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 Detroit to Chicago
Explore current cheapest deals departing from Detroit to Chicago
Round trip
Sort by: Cheapest
October 6 - October 13
DTW - Chicago
$142
$156
Round trip
July 14 - July 21
DTW - Chicago
$156
$158
Round trip
July 8 - July 15
DTW - Chicago
$140
$158
Round trip
October 21 - October 31
DTW - Chicago
$133
$177
Round trip
September 23 - September 30
DTW - Chicago
$124
$178
Round trip
November 3 - November 4
DTW - Chicago
$164
$178
Round trip
July 4 - July 7
DTW - Chicago
$281
$187
Round trip
July 4 - July 11
DTW - Chicago
$261
$187
Round trip
October 13 - October 20
DTW - Chicago
$238
$192
Round trip
September 10 - September 28
DTW - Chicago
$173
$193
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 Detroit to Chicago
How much is a round trip from Detroit to Chicago
Regular price: $110 - $185
Prices for flights from Detroit to Chicago are currently within the regular range.
The regular price range for flights from Detroit to Chicago is $110 to $185. The current lowest deal is $156 with United Airlines, for travel from Oct 6-Oct 13.
now $156
Low $110
High $185
The cheapest time to fly from Detroit to Chicago
Flights from DTT to CHI are cheapest in August, with a median price of $186. The most expensive month to fly is February, with a median price of $1009. Prices are generally lower from March to October.
August
Flights from $186
February
Flights from $1,009
Direct flights from Detroit to Chicago
Deutsche Luft Hansa
United Airlines
Last-minute flights going from Detroit to Chicago
Fri, Jun 19
DTW - Chicago
Detroit (DTW) - Chicago (MDW)
Frontier Airlines
$384
$316
One-way
Tue, Jun 23
DTW - Chicago
Detroit (DTW) - Chicago (MDW)
Frontier Airlines
$333
$284
One-way
Tue, Jun 23
DTW - Chicago
Detroit (DTW) - Chicago (MDW)
Frontier Airlines
$326
$284
One-way
Wed, Jun 24
DTW - Chicago
Detroit (DTW) - Chicago (MDW)
Frontier Airlines
$315
$284
One-way
Thu, Jul 2
DTW - Chicago
Detroit (DTW) - Chicago (MDW)
Frontier Airlines
$283
$269
One-way
Sat, Jul 4
DTW - Chicago
Detroit (DTW) - Chicago (MDW)
$281
$187
One-way
Biggest price drops on these dates for flights from Detroit to Chicago
Jul 4 - Jul 7
$281 → $187
33%
Jul 4 - Jul 11
$261 → $187
28%
Jun 19 - Jun 20
$384 → $316
18%
Jun 23 - Jun 24
$333 → $284
15%
Popular Airports to fly from Detroit to Chicago
Detroit - Chicago route insights
💸 Price insights
Recent fares are near the typical level
Recent fares from Detroit to Chicago are near the typical level, with a median price of $227.
📅 Best time to fly
August is historically the cheapest month
Historically, August is the cheapest month to fly from Detroit to Chicago, with a median price of $186.
⏱️ Flight duration
Direct flights average 2h 50m
The median flight time for direct routes from Detroit to Chicago is 2h 50m.
✈️ Airlines & availability
Frequent deals are available
Deals for flights from Detroit to Chicago are frequent, with over 1 deal per day historically.
🏆 Airline highlight
United Airlines offers direct flights
United Airlines is one of the airlines that historically offers direct flights on this route.
🎯 Booking tip
Consider flights with stopovers
While 59.9% of deals are direct, connecting flights typically have 2 stopovers.
Detroit main airports to depart from
Detroit Metropolitan (DTW)
Detroit Metropolitan Airport is a convenient departure point for flights to Chicago.
📍 ~30 km from Detroit city center (reachable by car)
💸 Flights from ~$156
Chicago main airports to arrive at
O Hare International (ORD)
O'Hare International Airport is a major hub for flights to Chicago from Detroit.
📍 ~23 km from Chicago city center (reachable by car, train, bus)
💸 Flights from ~$156
Chicago Midway International (MDW)
Chicago Midway International Airport offers another convenient option for flights from Detroit to Chicago.
📍 ~15 km from Chicago city center (reachable by car, train, bus)
💸 Flights from ~$158
Chicago Rockford International (RFD)
Chicago Rockford International Airport serves as an alternative arrival point for flights to Chicago.
📍 ~115 km from Chicago city center (reachable by car)
💸 Flights from ~$210
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
This airport offers excellent proximity to Chicago with high-frequency flight options and direct rail access.
📍 ~135 km from Chicago (reachable by rail)
💸 Flights from ~$311
South Bend International (SBN)
This airport is geographically the closest alternative to Chicago, with direct commuter rail connections.
📍 ~120 km from Chicago (reachable by rail)
💸 Flights from ~$208
Gerald R. Ford International (GRR)
This major regional hub is a good alternative for travelers on the eastern side of the Chicago metro area.
📍 ~230 km from Chicago (reachable by car)
💸 Flights from ~$241
Dane County Regional (MSN)
This reliable regional airport offers consistent service and is less congested than major Chicago hubs.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$293
Fort Wayne International (FWA)
This airport provides stable regional service and is an alternative for southeastern Chicago suburbs.
📍 ~240 km from Chicago (reachable by car)
💸 Flights from ~$227
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from Detroit to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From DTW
Elite
Jun 16
Chicago, United States
74% AI deal score
$1,377
$469
Save $908
From DTW
Elite
Aug 27
Chicago, United States
72% AI deal score
$3,716
$1,865
Save $1,851
From DTW
Elite
Aug 27
Chicago, United States
72% AI deal score
$3,740
$1,865
Save $1,875
From DTW
Elite
Aug 08
Chicago, United States
72% AI deal score
$3,594
$1,900
Save $1,694
From DTW
Elite
Aug 08
Chicago, United States
72% AI deal score
$3,594
$1,900
Save $1,694
From DTW
Elite
Oct 23
Chicago, United States
72% AI deal score
$3,714
$1,916
Save $1,798
From DTW
Elite
Aug 25
Chicago, United States
72% AI deal score
$3,705
$1,921
Save $1,784
From DTW
Elite
Oct 03
Chicago, United States
71% AI deal score
$3,491
$1,835
Save $1,656
From DTW
Elite
Oct 15
Chicago, United States
71% AI deal score
$3,592
$1,865
Save $1,727
From DTW
Elite
Oct 15
Chicago, United States
71% AI deal score
$3,588
$1,865
Save $1,723
From DTW
Elite
Jul 07
Chicago, United States
71% AI deal score
$3,425
$1,922
Save $1,503
From DTW
Elite
Jun 16
Chicago, United States
69% AI deal score
$830
$580
Save $250
From DTW
Elite
Jun 17
Chicago, United States
69% AI deal score
$1,350
$948
Save $402
From DTW
Elite
Oct 03
Chicago, United States
67% AI deal score
$3,433
$1,835
Save $1,598
From DTW
Elite
Sep 24
Chicago, United States
67% AI deal score
$3,418
$1,857
Save $1,561
From DTW
Elite
Oct 02
Chicago, United States
67% AI deal score
$3,445
$1,865
Save $1,580
From DTW
Elite
Oct 02
Chicago, United States
67% AI deal score
$3,483
$1,865
Save $1,618
From DTW
Elite
Oct 03
Chicago, United States
67% AI deal score
$3,548
$1,891
Save $1,657
From DTW
Elite
Oct 03
Chicago, United States
67% AI deal score
$3,433
$1,891
Save $1,542
From DTW
Elite
Oct 03
Chicago, United States
67% AI deal score
$3,548
$1,891
Save $1,657
From DTW
Elite
Oct 03
Chicago, United States
67% AI deal score
$3,433
$1,891
Save $1,542
From DTW
Elite
Oct 03
Chicago, United States
67% AI deal score
$3,490
$1,900
Save $1,590
From DTW
Elite
Oct 14
Chicago, United States
67% AI deal score
$3,582
$1,916
Save $1,666
From DTW
Elite
Oct 14
Chicago, United States
67% AI deal score
$3,575
$1,916
Save $1,659
From DTW
Elite
Oct 09
Chicago, United States
67% AI deal score
$3,538
$1,919
Save $1,619
From DTW
Elite
Oct 09
Chicago, United States
67% AI deal score
$3,586
$1,919
Save $1,667
From DTW
Elite
Oct 23
Chicago, United States
67% AI deal score
$3,507
$1,943
Save $1,564
From DTW
Elite
Jul 14
Chicago, United States
67% AI deal score
$3,567
$2,007
Save $1,560
From DTW
Elite
Aug 16
Chicago, United States
67% AI deal score
$3,767
$2,093
Save $1,674
From DTW
Elite
Jul 05
Chicago, United States
67% AI deal score
$3,658
$2,128
Save $1,530
From DTW
Elite
Jul 13
Chicago, United States
67% AI deal score
$3,799
$2,150
Save $1,649
From DTW
Elite
Jun 25
Chicago, United States
67% AI deal score
$4,174
$2,315
Save $1,859
From DTW
Elite
Jun 17
Chicago, United States
67% AI deal score
$4,546
$2,440
Save $2,106
From DTW
Elite
Aug 05
Chicago, United States
67% AI deal score
$588
$452
Save $136
From DTW
Elite
Nov 02
Chicago, United States
66% AI deal score
$3,077
$1,835
Save $1,242
From DTW
Elite
Nov 01
Chicago, United States
66% AI deal score
$3,080
$1,835
Save $1,245
From DTW
Elite
Nov 01
Chicago, United States
66% AI deal score
$3,093
$1,886
Save $1,207
From DTW
Elite
Nov 02
Chicago, United States
66% AI deal score
$3,121
$1,887
Save $1,234
From DTW
Elite
Sep 21
Chicago, United States
66% AI deal score
$3,392
$1,968
Save $1,424
From DTW
Elite
Jul 28
Chicago, United States
66% AI deal score
$3,589
$2,205
Save $1,384
From DTW
Elite
Jul 29
Chicago, United States
66% AI deal score
$3,575
$2,270
Save $1,305
From DTW
Elite
Aug 04
Chicago, United States
66% AI deal score
$3,715
$2,328
Save $1,387
From DTW
Elite
Jul 28
Chicago, United States
65% AI deal score
$3,420
$2,263
Save $1,157
From DTW
Elite
Jul 13
Chicago, United States
65% AI deal score
$3,423
$2,325
Save $1,098
From DTW
Elite
Jul 29
Chicago, United States
65% AI deal score
$3,439
$2,328
Save $1,111
From DTW
Elite
Jul 07
Chicago, United States
50% AI deal score
$3,592
$2,525
Save $1,067
From DTW
Elite
Aug 08
Chicago, United States
50% AI deal score
$3,744
$2,558
Save $1,186
From DTW
Elite
Aug 12
Chicago, United States
50% AI deal score
$558
$429
Save $129
From DTW
Elite
Aug 11
Chicago, United States
49% AI deal score
$516
$443
Save $73
From DTW
Elite
Sep 01
Chicago, United States
49% AI deal score
$554
$429
Save $125
From DTW
Elite
Aug 18
Chicago, United States
48% AI deal score
$500
$443
Save $57
From DTW
Elite
Sep 01
Chicago, United States
47% AI deal score
$479
$443
Save $36
From DTW
Elite
Jul 21
Chicago, United States
47% AI deal score
$459
$429
Save $30
From DTW
Elite
Jul 15
Chicago, United States
47% AI deal score
$459
$429
Save $30
From DTW
Elite
Jul 14
Chicago, United States
47% AI deal score
$459
$429
Save $30
From DTW
Elite
Jul 15
Chicago, United States
47% AI deal score
$459
$429
Save $30
From DTW
Elite
Jun 20
Chicago, United States
47% AI deal score
$702
$589
Save $113
From DTW
Elite
Jun 16
Chicago, United States
47% AI deal score
$720
$608
Save $112
From DTW
Elite
Jun 18
Chicago, United States
47% AI deal score
$1,254
$1,009
Save $245
From DTW
Elite
Sep 14
Chicago, United States
46% AI deal score
$3,693
$2,263
Save $1,430
From DTW
Elite
Sep 30
Chicago, United States
46% AI deal score
$469
$443
Save $26
From DTW
Elite
Sep 22
Chicago, United States
46% AI deal score
$469
$443
Save $26
From DTW
Elite
Jul 07
Chicago, United States
46% AI deal score
$473
$443
Save $30
From DTW
Elite
Jun 21
Chicago, United States
46% AI deal score
$705
$622
Save $83
From DTW
Elite
Jun 20
Chicago, United States
46% AI deal score
$705
$608
Save $97
From DTW
Elite
Jul 21
Chicago, United States
46% AI deal score
$1,129
$892
Save $237
From DTW
Elite
Jun 21
Chicago, United States
46% AI deal score
$1,251
$1,001
Save $250
From DTW
Elite
Jul 22
Chicago, United States
45% AI deal score
$457
$443
Save $14
From DTW
Elite
Nov 11
Chicago, United States
45% AI deal score
$465
$445
Save $20
From DTW
Elite
Jul 24
Chicago, United States
45% AI deal score
$1,138
$910
Save $228
From DTW
Elite
Jul 30
Chicago, United States
45% AI deal score
$1,130
$928
Save $202
From DTW
Elite
Jul 02
Chicago, United States
45% AI deal score
$1,137
$938
Save $199
From DTW
Elite
Jul 28
Chicago, United States
44% AI deal score
$447
$443
Save $4
From DTW
Elite
Jun 22
Chicago, United States
44% AI deal score
$675
$608
Save $67
From DTW
Elite
Jul 06
Chicago, United States
44% AI deal score
$1,107
$922
Save $185
From DTW
Elite
Jul 20
Chicago, United States
44% AI deal score
$1,113
$927
Save $186
From DTW
Elite
Oct 27
Chicago, United States
43% AI deal score
$443
From DTW
Elite
Nov 04
Chicago, United States
43% AI deal score
$443
From DTW
Elite
Nov 11
Chicago, United States
43% AI deal score
$443
From DTW
Elite
Dec 09
Chicago, United States
43% AI deal score
$443
From DTW
Elite
Oct 28
Chicago, United States
43% AI deal score
$443
From DTW
Elite
Oct 20
Chicago, United States
43% AI deal score
$443
From DTW
Elite
Jul 15
Chicago, United States
43% AI deal score
$443
From DTW
Elite
Oct 13
Chicago, United States
43% AI deal score
$443
From DTW
Elite
Nov 17
Chicago, United States
43% AI deal score
$459
From DTW
Elite
Dec 02
Chicago, United States
43% AI deal score
$438
From DTW
Elite
Nov 02
Chicago, United States
43% AI deal score
$474
From DTW
Elite
Nov 25
Chicago, United States
43% AI deal score
$481
From DTW
Elite
Jun 30
Chicago, United States
43% AI deal score
$524
$489
Save $35
From DTW
Elite
Jun 21
Chicago, United States
43% AI deal score
$1,214
$1,078
Save $136
From DTW
Elite
Nov 16
Chicago, United States
42% AI deal score
$461
From DTW
Elite
Oct 31
Chicago, United States
42% AI deal score
$461
From DTW
Elite
Sep 14
Chicago, United States
42% AI deal score
$1,065
$938
Save $127
From DTW
Elite
Jun 21
Chicago, United States
42% AI deal score
$659
$627
Save $32
From DTW
Elite
Jun 22
Chicago, United States
42% AI deal score
$667
$627
Save $40
From DTW
Elite
Jun 28
Chicago, United States
42% AI deal score
$1,154
$1,066
Save $88
From DTW
Elite
Nov 15
Chicago, United States
41% AI deal score
$515
From DTW
Elite
Jul 30
Chicago, United States
39% AI deal score
$515
From DTW
Elite
Jul 01
Chicago, United States
39% AI deal score
$558
From DTW
Elite
Jun 22
Chicago, United States
31% AI deal score
$907