Cheap Flights from Cleveland to Chicago
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Deals from
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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 Cleveland to Chicago
Explore current cheapest deals departing from Cleveland to Chicago
Round trip
Sort by: Cheapest
July 14 - July 21
CLE - Chicago
$132
$109
Round trip
July 14 - July 28
CLE - Chicago
$117
$109
Round trip
July 15 - July 22
CLE - Chicago
$132
$109
Round trip
July 15 - July 29
CLE - Chicago
$117
$109
Round trip
July 7 - July 14
CLE - Chicago
$134
$109
Round trip
July 8 - July 15
CLE - Chicago
$134
$109
Round trip
July 8 - July 22
CLE - Chicago
$120
$109
Round trip
July 22 - July 29
CLE - Chicago
$129
$109
Round trip
July 7 - July 21
CLE - Chicago
$119
$109
Round trip
July 8 - July 14
CLE - Chicago
$134
$109
Round trip
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Route Intelligence — 486,190 Searches this Week
Insights for flights from Cleveland to Chicago
How much is a round trip from Cleveland to Chicago
Regular price: $107 - $239
Prices for flights from Cleveland to Chicago are currently within the regular range.
The regular price range for flights from Cleveland to Chicago is between $107 and $239. The current lowest deal is $109 with United Airlines, for travel from Jul 14-Jul 21.
now $109
Low $107
High $239
The cheapest time to fly from Cleveland to Chicago
The cheapest month to fly from Cleveland to Chicago is January, with a median price of $139. The most expensive month is March, with a median price of $347. Prices are generally lower from January to December.
January
Flights from $139
March
Flights from $347
Direct flights from Cleveland to Chicago
American Airlines
Last-minute flights going from Cleveland to Chicago
Tue, Jun 30
CLE - Chicago
Cleveland (CLE) - Chicago (ORD)
$267
$157
One-way
Tue, Jun 30
CLE - Chicago
Cleveland (CLE) - Chicago (ORD)
$269
$157
One-way
Tue, Jun 30
CLE - Chicago
Cleveland (CLE) - Chicago (ORD)
$268
$157
One-way
Tue, Jun 30
CLE - Chicago
Cleveland (CLE) - Chicago (ORD)
$249
$157
One-way
Tue, Jun 30
CLE - Chicago
Cleveland (CLE) - Chicago (ORD)
$243
$157
One-way
Wed, Jul 1
CLE - Chicago
Cleveland (CLE) - Chicago (ORD)
American Airlines
$136
$123
One-way
Biggest price drops on these dates for flights from Cleveland to Chicago
Oct 27 - Nov 3
$252 → $109
57%
Jul 15 - Jul 22
$244 → $109
55%
Jul 3 - Jul 7
$266 → $133
50%
Aug 26 - Sep 2
$241 → $109
55%
Popular Airports to fly from Cleveland to Chicago
Cleveland - Chicago route insights
💸 Price insights
Recent fares are above the typical level.
Recent roundtrip fares from Cleveland to Chicago are above the typical level at $109.
📅 Best time to fly
January is historically the cheapest month to fly.
Historically, January is the cheapest month to fly from Cleveland to Chicago, with a median price of $139.
⏱️ Flight duration
Flights typically last 8h 16m.
The median flight duration from Cleveland to Chicago is 8h 16m, covering 492 km.
✈️ Airlines & availability
44.6% of recent deals are direct.
44.6% of recent flight deals from Cleveland to Chicago are direct, with 2 stopovers when connecting.
🏆 Airline highlight
American Airlines offers direct flights.
American Airlines is one of the carriers that offers direct flights from Cleveland to Chicago.
🎯 Booking tip
Deals are frequent for this route.
Deals for flights from Cleveland to Chicago are frequent, with over 1 deal per day historically.
Cleveland main airports to depart from
Cleveland Hopkins International (CLE)
Cleveland Hopkins International Airport is a good option for flights from Cleveland to Chicago.
📍 ~20 km from Cleveland (reachable by car or train)
💸 Flights from ~$109
Chicago main airports to arrive at
Chicago Midway International (MDW)
Chicago Midway International is a convenient option for flights from Cleveland to Chicago.
📍 ~15 km from Chicago (reachable by car)
💸 Flights from ~$109
Chicago Rockford International (RFD)
Chicago Rockford International serves the wider Chicago area for your trip from Cleveland.
📍 ~120 km from Chicago (reachable by car)
💸 Flights from ~$190
O Hare International (ORD)
O Hare International is a major airport for travelers flying from Cleveland to Chicago.
📍 ~25 km from Chicago (reachable by car)
💸 Flights from ~$109
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 rail; travel time can be affected by heavy traffic on the I-94 corridor).
💸 Flights from ~$241
South Bend International (SBN)
South Bend International is the geographically closest alternative to Chicago, with direct commuter rail links.
📍 ~120 km from Chicago (reachable by rail; fewer direct flight destinations compared to Milwaukee or Chicago).
💸 Flights from ~$191
Gerald R. Ford International (GRR)
Gerald R. Ford International is a major regional hub, good for travelers on the eastern side of the Chicago metro area.
📍 ~205 km from Chicago (requires a significant drive, over 2 hours, from central Chicago).
💸 Flights from ~$205
Dane County Regional (MSN)
Dane County Regional is a reliable regional airport with consistent service and less congestion.
📍 ~200 km from Chicago (distance exceeds 190km, making it a secondary choice to MKE).
💸 Flights from ~$267
Fort Wayne International (FWA)
Fort Wayne International provides stable regional service, useful for southeastern Chicago suburbs.
📍 ~240 km from Chicago (significant distance from Chicago and limited flight frequency).
💸 Flights from ~$212
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from Cleveland to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From CLE
Elite
Aug 11
Chicago, United States
79% AI deal score
$615
$329
Save $286
From CLE
Elite
Aug 18
Chicago, United States
78% AI deal score
$605
$329
Save $276
From CLE
Elite
Oct 27
Chicago, United States
78% AI deal score
$1,265
$423
Save $842
From CLE
Elite
Oct 27
Chicago, United States
78% AI deal score
$1,364
$439
Save $925
From CLE
Elite
Oct 28
Chicago, United States
78% AI deal score
$1,408
$439
Save $969
From CLE
Elite
Jul 01
Chicago, United States
77% AI deal score
$547
$343
Save $204
From CLE
Elite
Jun 30
Chicago, United States
77% AI deal score
$575
$357
Save $218
From CLE
Elite
Oct 27
Chicago, United States
77% AI deal score
$1,187
$423
Save $764
From CLE
Elite
Oct 28
Chicago, United States
77% AI deal score
$1,183
$423
Save $760
From CLE
Elite
Oct 28
Chicago, United States
77% AI deal score
$1,187
$423
Save $764
From CLE
Elite
Oct 27
Chicago, United States
77% AI deal score
$1,183
$439
Save $744
From CLE
Elite
Oct 27
Chicago, United States
77% AI deal score
$1,265
$439
Save $826
From CLE
Elite
Oct 28
Chicago, United States
77% AI deal score
$1,317
$439
Save $878
From CLE
Elite
Oct 28
Chicago, United States
77% AI deal score
$1,265
$439
Save $826
From CLE
Elite
Sep 24
Chicago, United States
77% AI deal score
$1,302
$624
Save $678
From CLE
Elite
Aug 26
Chicago, United States
77% AI deal score
$876
$323
Save $553
From CLE
Elite
Jul 24
Chicago, United States
76% AI deal score
$1,505
$757
Save $748
From CLE
Elite
Nov 03
Chicago, United States
76% AI deal score
$554
$323
Save $231
From CLE
Elite
Jul 14
Chicago, United States
76% AI deal score
$492
$323
Save $169
From CLE
Elite
Jul 07
Chicago, United States
76% AI deal score
$498
$323
Save $175
From CLE
Elite
Jul 08
Chicago, United States
76% AI deal score
$491
$323
Save $168
From CLE
Elite
Oct 29
Chicago, United States
75% AI deal score
$863
$439
Save $424
From CLE
Elite
Jul 28
Chicago, United States
75% AI deal score
$956
$480
Save $476
From CLE
Elite
Nov 06
Chicago, United States
75% AI deal score
$1,408
$718
Save $690
From CLE
Elite
Jun 29
Chicago, United States
75% AI deal score
$1,681
$851
Save $830
From CLE
Elite
Sep 01
Chicago, United States
75% AI deal score
$775
$323
Save $452
From CLE
Elite
Oct 24
Chicago, United States
74% AI deal score
$781
$439
Save $342
From CLE
Elite
Oct 24
Chicago, United States
74% AI deal score
$781
$439
Save $342
From CLE
Elite
Oct 26
Chicago, United States
74% AI deal score
$780
$439
Save $341
From CLE
Elite
Oct 26
Chicago, United States
74% AI deal score
$780
$439
Save $341
From CLE
Elite
Oct 29
Chicago, United States
74% AI deal score
$757
$439
Save $318
From CLE
Elite
Sep 24
Chicago, United States
74% AI deal score
$1,287
$718
Save $569
From CLE
Elite
Jul 06
Chicago, United States
74% AI deal score
$1,512
$839
Save $673
From CLE
Elite
Sep 02
Chicago, United States
74% AI deal score
$1,630
$816
Save $814
From CLE
Elite
Sep 03
Chicago, United States
74% AI deal score
$1,661
$858
Save $803
From CLE
Elite
Oct 27
Chicago, United States
73% AI deal score
$438
$332
Save $106
From CLE
Elite
Sep 06
Chicago, United States
73% AI deal score
$453
$343
Save $110
From CLE
Elite
Oct 26
Chicago, United States
73% AI deal score
$755
$455
Save $300
From CLE
Elite
Oct 13
Chicago, United States
73% AI deal score
$862
$480
Save $382
From CLE
Elite
Sep 03
Chicago, United States
73% AI deal score
$1,286
$578
Save $708
From CLE
Elite
Jun 30
Chicago, United States
73% AI deal score
$557
$351
Save $206
From CLE
Elite
Oct 20
Chicago, United States
72% AI deal score
$480
$372
Save $108
From CLE
Elite
Aug 26
Chicago, United States
72% AI deal score
$1,785
$815
Save $970
From CLE
Elite
Oct 21
Chicago, United States
71% AI deal score
$475
$372
Save $103
From CLE
Elite
Jul 24
Chicago, United States
71% AI deal score
$1,487
$928
Save $559
From CLE
Elite
Jul 17
Chicago, United States
70% AI deal score
$790
$537
Save $253
From CLE
Elite
Aug 15
Chicago, United States
69% AI deal score
$1,141
$677
Save $464
From CLE
Elite
Oct 21
Chicago, United States
67% AI deal score
$457
$372
Save $85
From CLE
Elite
Oct 20
Chicago, United States
66% AI deal score
$441
$372
Save $69
From CLE
Elite
Oct 02
Chicago, United States
49% AI deal score
$2,592
$1,986
Save $606
From CLE
Elite
Oct 13
Chicago, United States
49% AI deal score
$2,650
$2,071
Save $579
From CLE
Elite
Oct 14
Chicago, United States
49% AI deal score
$2,618
$2,117
Save $501
From CLE
Elite
Oct 21
Chicago, United States
49% AI deal score
$467
$413
Save $54
From CLE
Elite
Nov 14
Chicago, United States
49% AI deal score
$537
$450
Save $87
From CLE
Elite
Oct 14
Chicago, United States
48% AI deal score
$2,645
$2,162
Save $483
From CLE
Elite
Jun 16
Chicago, United States
48% AI deal score
$2,908
$2,493
Save $415
From CLE
Elite
Oct 20
Chicago, United States
48% AI deal score
$457
$413
Save $44
From CLE
Elite
Sep 26
Chicago, United States
47% AI deal score
$830
$617
Save $213
From CLE
Elite
Aug 19
Chicago, United States
47% AI deal score
$1,126
$779
Save $347
From CLE
Elite
Oct 03
Chicago, United States
46% AI deal score
$2,563
$2,371
Save $192
From CLE
Elite
Sep 02
Chicago, United States
46% AI deal score
$420
$372
Save $48
From CLE
Elite
Jun 20
Chicago, United States
46% AI deal score
$687
$585
Save $102
From CLE
Elite
Oct 24
Chicago, United States
45% AI deal score
$2,621
$1,921
Save $700
From CLE
Elite
Oct 24
Chicago, United States
45% AI deal score
$2,608
$1,921
Save $687
From CLE
Elite
Oct 24
Chicago, United States
45% AI deal score
$2,611
$1,921
Save $690
From CLE
Elite
Oct 27
Chicago, United States
45% AI deal score
$2,623
$1,921
Save $702
From CLE
Elite
Oct 28
Chicago, United States
45% AI deal score
$2,616
$1,921
Save $695
From CLE
Elite
Oct 29
Chicago, United States
45% AI deal score
$2,653
$1,921
Save $732
From CLE
Elite
Oct 29
Chicago, United States
45% AI deal score
$2,628
$1,921
Save $707
From CLE
Elite
Oct 29
Chicago, United States
45% AI deal score
$2,621
$1,921
Save $700
From CLE
Elite
Oct 30
Chicago, United States
45% AI deal score
$2,652
$1,921
Save $731
From CLE
Elite
Oct 30
Chicago, United States
45% AI deal score
$2,651
$1,921
Save $730
From CLE
Elite
Oct 30
Chicago, United States
45% AI deal score
$2,615
$1,921
Save $694
From CLE
Elite
Oct 30
Chicago, United States
45% AI deal score
$2,616
$1,921
Save $695
From CLE
Elite
Oct 30
Chicago, United States
45% AI deal score
$2,626
$1,921
Save $705
From CLE
Elite
Oct 24
Chicago, United States
45% AI deal score
$2,629
$1,986
Save $643
From CLE
Elite
Oct 26
Chicago, United States
45% AI deal score
$2,623
$1,986
Save $637
From CLE
Elite
Oct 26
Chicago, United States
45% AI deal score
$2,626
$1,986
Save $640
From CLE
Elite
Oct 29
Chicago, United States
45% AI deal score
$2,681
$1,986
Save $695
From CLE
Elite
Oct 30
Chicago, United States
45% AI deal score
$2,710
$1,986
Save $724
From CLE
Elite
Jul 10
Chicago, United States
45% AI deal score
$2,478
$2,436
Save $42
From CLE
Elite
Jul 12
Chicago, United States
45% AI deal score
$2,471
$2,436
Save $35
From CLE
Elite
Jul 10
Chicago, United States
45% AI deal score
$2,478
$2,437
Save $41
From CLE
Elite
Jul 12
Chicago, United States
45% AI deal score
$2,471
$2,437
Save $34
From CLE
Elite
Jul 30
Chicago, United States
45% AI deal score
$2,554
$2,487
Save $67
From CLE
Elite
Jul 30
Chicago, United States
45% AI deal score
$2,570
$2,488
Save $82
From CLE
Elite
Jun 25
Chicago, United States
45% AI deal score
$2,520
$2,497
Save $23
From CLE
Elite
Jun 29
Chicago, United States
45% AI deal score
$1,119
$930
Save $189
From CLE
Elite
Oct 24
Chicago, United States
44% AI deal score
$2,622
$2,032
Save $590
From CLE
Elite
Oct 25
Chicago, United States
44% AI deal score
$2,622
$2,032
Save $590
From CLE
Elite
Oct 25
Chicago, United States
44% AI deal score
$2,621
$2,032
Save $589
From CLE
Elite
Oct 25
Chicago, United States
44% AI deal score
$2,623
$2,032
Save $591
From CLE
Elite
Oct 25
Chicago, United States
44% AI deal score
$2,626
$2,032
Save $594
From CLE
Elite
Oct 25
Chicago, United States
44% AI deal score
$2,608
$2,032
Save $576
From CLE
Elite
Oct 27
Chicago, United States
44% AI deal score
$2,618
$2,032
Save $586
From CLE
Elite
Oct 28
Chicago, United States
44% AI deal score
$2,649
$2,032
Save $617
From CLE
Elite
Oct 29
Chicago, United States
44% AI deal score
$2,654
$2,032
Save $622
From CLE
Elite
Oct 30
Chicago, United States
44% AI deal score
$2,679
$2,032
Save $647
From CLE
Elite
Oct 26
Chicago, United States
44% AI deal score
$2,618
$2,051
Save $567
From CLE
Elite
Oct 25
Chicago, United States
44% AI deal score
$2,618
$2,097
Save $521