Cheap Flights from Cleveland to Chicago
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Deals from
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Prices updated 4 days ago
402 airlines compared
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Fares are subject to change and may not be available for all dates. (Data last updated Jul 19, 2026.)
Today’s best flight deals from Cleveland to Chicago
Explore current cheapest deals departing from Cleveland to Chicago
Round trip
Sort by: Cheapest
August 11 - August 15
CLE - Chicago
$157
$117
Round trip
August 4 - August 5
CLE - Chicago
$150
$117
Round trip
August 11 - August 13
CLE - Chicago
$158
$117
Round trip
August 15 - August 22
CLE - Chicago
$144
$117
Round trip
August 29 - August 31
CLE - Chicago
$151
$117
Round trip
August 12 - August 13
CLE - Chicago
$143
$117
Round trip
August 5 - August 8
CLE - Chicago
$161
$117
Round trip
August 18 - August 20
CLE - Chicago
$155
$117
Round trip
August 6 - August 13
CLE - Chicago
$132
$117
Round trip
August 13 - August 18
CLE - Chicago
$151
$117
Round trip
Unlock all 500+ flight deals to Chicago and get alerts when great deals appear
Cleveland to Chicago: Overview
Insights for flights from Cleveland to Chicago
How much is a round trip from Cleveland to Chicago
Regular price: $114 - $341
Prices for flights from Cleveland to Chicago are currently within the regular range.
The regular price range for flights from Cleveland to Chicago is typically between $114 and $341. The current lowest deal is $117 with American Airlines, for travel from Aug 11-Aug 15.
now $117
Low $114
High $341
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 August, with a median price of $371. Prices are generally lower from January to December.
January
Flights from $139
August
Flights from $371
Direct flights from Cleveland to Chicago
Southwest Airlines
United Airlines
Last-minute flights going from Cleveland to Chicago
Tue, Aug 4
CLE - Chicago
Cleveland (CLE) - Chicago (MDW)
Southwest Airlines
$149
$117
One-way
Tue, Aug 4
CLE - Chicago
Cleveland (CLE) - Chicago (ORD)
Frontier Airlines
$281
$205
One-way
Wed, Aug 5
CLE - Chicago
Cleveland (CLE) - Chicago (ORD)
American Airlines
$160
$117
One-way
Wed, Aug 5
CLE - Chicago
Cleveland (CLE) - Chicago (RFD)
Frontier Airlines
$269
$211
One-way
Thu, Aug 6
CLE - Chicago
Cleveland (CLE) - Chicago (MDW)
Southwest Airlines
$132
$117
One-way
Thu, Aug 6
CLE - Chicago
Cleveland (CLE) - Chicago (MDW)
Southwest Airlines
$146
$117
One-way
Biggest price drops on these dates for flights from Cleveland to Chicago
Aug 8 - Aug 11
$273 → $117
57%
Oct 28 - Oct 31
$263 → $117
56%
Aug 8 - Aug 13
$261 → $117
55%
Aug 27 - Aug 31
$258 → $117
55%
Popular Airports to fly from Cleveland to Chicago
Cleveland - Chicago route insights
💸 Price insights
Recent fares are above the typical level
Recent fares from Cleveland to Chicago are above the typical level at $117.
📅 Best time to fly
January is historically cheapest at $139
Historically, January, February, and November offer the lowest median prices for this route.
⏱️ Flight duration
Direct flights take 1h 36m
Direct flights typically take 1 hour 36 minutes, while connecting flights average 16 hours 48 minutes.
✈️ Airlines & availability
Southwest and United offer direct flights
Southwest Airlines and United Airlines have offered direct flights on this route recently.
🏆 Airline highlight
American Airlines offers a deal at $117
American Airlines recently offered a deal for $117 from August 11-August 15.
🎯 Booking tip
Deals are frequent on this route
Deals for flights from Cleveland to Chicago are frequent, appearing within a 30-day window.
Cleveland main airports to depart from
Cleveland Hopkins International (CLE)
Cleveland Hopkins International Airport is a convenient departure point for flights to Chicago.
📍 ~16 km from Cleveland (reachable by car or train)
💸 Flights from ~$117
Chicago main airports to arrive at
Chicago Midway International (MDW)
Chicago Midway International is a convenient arrival airport for flights from Cleveland to Chicago.
📍 ~14 km from Chicago city center (reachable by car)
💸 Flights from ~$117
Chicago Rockford International (RFD)
Chicago Rockford International offers an alternative arrival option for your trip to Chicago.
📍 ~126 km from Chicago city center (reachable by car)
💸 Flights from ~$195
O Hare International (ORD)
O Hare International is a major hub for travelers flying from Cleveland to Chicago.
📍 ~25 km from Chicago city center (reachable by car)
💸 Flights from ~$117
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
General Mitchell International offers significant carrier presence and direct flight options for Chicago travelers.
📍 ~135 km from Chicago (reachable by car or train)
💸 Flights from ~$210
Gerald R. Ford International (GRR)
Gerald R. Ford International provides a robust domestic network with legacy and low-cost airlines.
📍 ~250 km from Chicago (reachable by car)
💸 Flights from ~$212
Dane County Regional (MSN)
Dane County Regional is a reliable regional hub with efficient operations and good amenities for travelers.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$267
South Bend International (SBN)
South Bend International is the closest alternative airport to the Chicago metro area.
📍 ~120 km from Chicago (reachable by train)
💸 Flights from ~$203
Fort Wayne International (FWA)
Fort Wayne International offers multiple cabin classes and solid connectivity for eastern domestic destinations.
📍 ~235 km from Chicago (reachable by car)
💸 Flights from ~$237
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
Oct 13
Chicago, United States
78% AI deal score
$1,381
$423
Save $958
From CLE
Elite
Oct 13
Chicago, United States
78% AI deal score
$1,332
$423
Save $909
From CLE
Elite
Oct 14
Chicago, United States
78% AI deal score
$1,370
$423
Save $947
From CLE
Elite
Oct 13
Chicago, United States
78% AI deal score
$1,386
$439
Save $947
From CLE
Elite
Oct 14
Chicago, United States
78% AI deal score
$1,381
$439
Save $942
From CLE
Elite
Oct 13
Chicago, United States
77% AI deal score
$1,160
$423
Save $737
From CLE
Elite
Oct 14
Chicago, United States
77% AI deal score
$1,155
$423
Save $732
From CLE
Elite
Sep 24
Chicago, United States
77% AI deal score
$1,316
$439
Save $877
From CLE
Elite
Oct 13
Chicago, United States
77% AI deal score
$1,155
$439
Save $716
From CLE
Elite
Oct 14
Chicago, United States
77% AI deal score
$1,286
$439
Save $847
From CLE
Elite
Aug 27
Chicago, United States
77% AI deal score
$1,864
$592
Save $1,272
From CLE
Elite
Oct 13
Chicago, United States
76% AI deal score
$1,370
$480
Save $890
From CLE
Elite
Oct 14
Chicago, United States
76% AI deal score
$1,386
$480
Save $906
From CLE
Elite
Aug 14
Chicago, United States
76% AI deal score
$1,889
$648
Save $1,241
From CLE
Elite
Aug 14
Chicago, United States
76% AI deal score
$1,908
$929
Save $979
From CLE
Elite
Aug 06
Chicago, United States
75% AI deal score
$658
$415
Save $243
From CLE
Elite
Oct 17
Chicago, United States
75% AI deal score
$862
$423
Save $439
From CLE
Elite
Oct 15
Chicago, United States
75% AI deal score
$871
$439
Save $432
From CLE
Elite
Oct 17
Chicago, United States
75% AI deal score
$871
$439
Save $432
From CLE
Elite
Oct 12
Chicago, United States
75% AI deal score
$1,160
$496
Save $664
From CLE
Elite
Jul 28
Chicago, United States
75% AI deal score
$1,055
$521
Save $534
From CLE
Elite
Jan 21
Chicago, United States
75% AI deal score
$1,328
$537
Save $791
From CLE
Elite
Jan 22
Chicago, United States
75% AI deal score
$1,328
$537
Save $791
From CLE
Elite
Jan 23
Chicago, United States
75% AI deal score
$1,328
$537
Save $791
From CLE
Elite
Jul 19
Chicago, United States
75% AI deal score
$1,653
$659
Save $994
From CLE
Elite
Jul 05
Chicago, United States
75% AI deal score
$1,427
$714
Save $713
From CLE
Elite
Oct 15
Chicago, United States
74% AI deal score
$822
$439
Save $383
From CLE
Elite
Oct 15
Chicago, United States
74% AI deal score
$848
$455
Save $393
From CLE
Elite
Aug 07
Chicago, United States
73% AI deal score
$665
$456
Save $209
From CLE
Elite
Aug 02
Chicago, United States
73% AI deal score
$671
$456
Save $215
From CLE
Elite
Aug 16
Chicago, United States
73% AI deal score
$657
$456
Save $201
From CLE
Elite
Oct 01
Chicago, United States
73% AI deal score
$890
$496
Save $394
From CLE
Elite
Jul 07
Chicago, United States
73% AI deal score
$1,443
$789
Save $654
From CLE
Elite
Jul 04
Chicago, United States
73% AI deal score
$1,397
$800
Save $597
From CLE
Elite
Jul 04
Chicago, United States
73% AI deal score
$1,445
$815
Save $630
From CLE
Elite
Jul 19
Chicago, United States
73% AI deal score
$1,702
$969
Save $733
From CLE
Elite
Jul 24
Chicago, United States
72% AI deal score
$594
$458
Save $136
From CLE
Elite
Oct 15
Chicago, United States
72% AI deal score
$869
$496
Save $373
From CLE
Elite
Oct 16
Chicago, United States
72% AI deal score
$862
$496
Save $366
From CLE
Elite
Sep 29
Chicago, United States
72% AI deal score
$1,124
$581
Save $543
From CLE
Elite
Nov 06
Chicago, United States
72% AI deal score
$1,406
$638
Save $768
From CLE
Elite
Oct 09
Chicago, United States
71% AI deal score
$869
$537
Save $332
From CLE
Elite
Jul 09
Chicago, United States
71% AI deal score
$1,263
$786
Save $477
From CLE
Elite
Aug 01
Chicago, United States
69% AI deal score
$1,218
$739
Save $479
From CLE
Elite
Jul 08
Chicago, United States
69% AI deal score
$1,278
$880
Save $398
From CLE
Elite
Oct 15
Chicago, United States
68% AI deal score
$862
$592
Save $270
From CLE
Elite
Jul 14
Chicago, United States
68% AI deal score
$1,023
$764
Save $259
From CLE
Elite
Sep 09
Chicago, United States
65% AI deal score
$2,841
$1,887
Save $954
From CLE
Elite
Jul 31
Chicago, United States
65% AI deal score
$532
$458
Save $74
From CLE
Elite
Sep 20
Chicago, United States
50% AI deal score
$2,818
$1,870
Save $948
From CLE
Elite
Sep 07
Chicago, United States
50% AI deal score
$2,738
$1,887
Save $851
From CLE
Elite
Sep 08
Chicago, United States
50% AI deal score
$2,807
$1,887
Save $920
From CLE
Elite
Sep 05
Chicago, United States
50% AI deal score
$2,802
$1,892
Save $910
From CLE
Elite
Sep 04
Chicago, United States
50% AI deal score
$2,730
$1,892
Save $838
From CLE
Elite
Sep 09
Chicago, United States
50% AI deal score
$2,796
$1,935
Save $861
From CLE
Elite
Oct 05
Chicago, United States
50% AI deal score
$479
$415
Save $64
From CLE
Elite
Sep 05
Chicago, United States
49% AI deal score
$2,691
$1,887
Save $804
From CLE
Elite
Sep 01
Chicago, United States
49% AI deal score
$2,705
$1,887
Save $818
From CLE
Elite
Sep 04
Chicago, United States
49% AI deal score
$2,696
$1,887
Save $809
From CLE
Elite
Sep 03
Chicago, United States
49% AI deal score
$2,718
$1,891
Save $827
From CLE
Elite
Sep 01
Chicago, United States
49% AI deal score
$2,712
$1,892
Save $820
From CLE
Elite
Sep 03
Chicago, United States
49% AI deal score
$2,730
$1,897
Save $833
From CLE
Elite
Sep 05
Chicago, United States
49% AI deal score
$2,700
$1,925
Save $775
From CLE
Elite
Sep 04
Chicago, United States
49% AI deal score
$2,693
$1,925
Save $768
From CLE
Elite
Sep 07
Chicago, United States
49% AI deal score
$2,712
$1,925
Save $787
From CLE
Elite
Sep 01
Chicago, United States
49% AI deal score
$2,697
$1,925
Save $772
From CLE
Elite
Sep 08
Chicago, United States
49% AI deal score
$2,738
$1,925
Save $813
From CLE
Elite
Sep 03
Chicago, United States
49% AI deal score
$2,718
$1,952
Save $766
From CLE
Elite
Aug 13
Chicago, United States
49% AI deal score
$2,635
$1,961
Save $674
From CLE
Elite
Sep 02
Chicago, United States
49% AI deal score
$2,702
$1,967
Save $735
From CLE
Elite
Oct 27
Chicago, United States
49% AI deal score
$2,582
$2,034
Save $548
From CLE
Elite
Oct 13
Chicago, United States
49% AI deal score
$2,703
$2,119
Save $584
From CLE
Elite
Oct 13
Chicago, United States
49% AI deal score
$471
$417
Save $54
From CLE
Elite
Aug 31
Chicago, United States
48% AI deal score
$2,376
$1,887
Save $489
From CLE
Elite
Aug 31
Chicago, United States
48% AI deal score
$2,386
$1,892
Save $494
From CLE
Elite
Aug 19
Chicago, United States
48% AI deal score
$2,452
$1,956
Save $496
From CLE
Elite
Aug 19
Chicago, United States
48% AI deal score
$2,452
$1,961
Save $491
From CLE
Elite
Aug 13
Chicago, United States
48% AI deal score
$2,462
$1,961
Save $501
From CLE
Elite
Aug 13
Chicago, United States
48% AI deal score
$2,465
$1,961
Save $504
From CLE
Elite
Aug 18
Chicago, United States
48% AI deal score
$2,455
$1,967
Save $488
From CLE
Elite
Aug 25
Chicago, United States
48% AI deal score
$2,373
$1,986
Save $387
From CLE
Elite
Sep 01
Chicago, United States
48% AI deal score
$2,654
$2,120
Save $534
From CLE
Elite
Sep 05
Chicago, United States
48% AI deal score
$2,674
$2,120
Save $554
From CLE
Elite
Sep 07
Chicago, United States
48% AI deal score
$2,692
$2,120
Save $572
From CLE
Elite
Sep 08
Chicago, United States
48% AI deal score
$2,692
$2,120
Save $572
From CLE
Elite
Sep 04
Chicago, United States
48% AI deal score
$2,677
$2,120
Save $557
From CLE
Elite
Sep 13
Chicago, United States
48% AI deal score
$2,753
$2,225
Save $528
From CLE
Elite
Sep 14
Chicago, United States
48% AI deal score
$449
$415
Save $34
From CLE
Elite
Aug 12
Chicago, United States
48% AI deal score
$1,144
$749
Save $395
From CLE
Elite
Jul 15
Chicago, United States
48% AI deal score
$1,002
$773
Save $229
From CLE
Elite
Jul 05
Chicago, United States
48% AI deal score
$1,443
$1,021
Save $422
From CLE
Elite
Aug 31
Chicago, United States
47% AI deal score
$2,370
$1,925
Save $445
From CLE
Elite
Aug 27
Chicago, United States
47% AI deal score
$2,377
$1,927
Save $450
From CLE
Elite
Aug 30
Chicago, United States
47% AI deal score
$2,370
$1,927
Save $443
From CLE
Elite
Aug 27
Chicago, United States
47% AI deal score
$2,346
$1,927
Save $419
From CLE
Elite
Aug 30
Chicago, United States
47% AI deal score
$2,386
$1,932
Save $454
From CLE
Elite
Aug 24
Chicago, United States
47% AI deal score
$2,392
$1,944
Save $448
From CLE
Elite
Aug 22
Chicago, United States
47% AI deal score
$2,374
$1,956
Save $418
From CLE
Elite
Aug 29
Chicago, United States
47% AI deal score
$2,369
$1,956
Save $413
From CLE
Elite
Aug 26
Chicago, United States
47% AI deal score
$2,342
$1,956
Save $386