Cheap Flights from Boston to Chicago
Browse current best options from Boston. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Boston
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
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 Boston to Chicago
Explore current cheapest deals departing from Boston to Chicago
Round trip
Sort by: Cheapest
August 4 - August 18
BOS - Chicago
$108
$127
Round trip
August 4 - August 19
BOS - Chicago
$106
$127
Round trip
August 5 - August 19
BOS - Chicago
$108
$127
Round trip
August 5 - August 10
BOS - Chicago
$131
$137
Round trip
August 17 - August 19
BOS - Chicago
$135
$140
Round trip
August 11 - August 26
BOS - Chicago
$108
$140
Round trip
September 23 - September 30
BOS - Chicago
$150
$140
Round trip
September 15 - September 17
BOS - Chicago
$145
$141
Round trip
September 15 - September 22
BOS - Chicago
$142
$141
Round trip
August 19 - August 25
BOS - Chicago
$128
$142
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 Boston to Chicago
How much is a round trip from Boston to Chicago
Regular price: $86 - $247
Prices for flights from Boston to Chicago are currently within the regular range.
The regular price range for flights from Boston to Chicago is between $86 and $247. The current lowest deal is $127 with JetBlue Airways, for travel from Aug 4-Aug 18.
now $127
Low $86
High $247
The cheapest time to fly from Boston to Chicago
Flights from Boston to Chicago are cheapest in November, with a median price of $103. The most expensive month to fly is December, with a median price of $1127. Prices are generally lower from January to November.
November
Flights from $103
December
Flights from $1,127
Direct flights from Boston to Chicago
JetBlue Airways
Last-minute flights going from Boston to Chicago
Wed, Jun 17
BOS - Chicago
Boston (BOS) - Chicago (MDW)
Frontier Airlines
$393
$257
One-way
Wed, Jul 1
BOS - Chicago
Boston (BOS) - Chicago (ORD)
American Airlines
$117
$149
One-way
Wed, Jul 1
BOS - Chicago
Boston (BOS) - Chicago (ORD)
JetBlue Airways
$237
$177
One-way
Sat, Jul 4
BOS - Chicago
Boston (BOS) - Chicago (ORD)
Deutsche Luft Hansa
$123
$149
One-way
Sat, Jul 4
BOS - Chicago
Boston (BOS) - Chicago (ORD)
$226
$149
One-way
Sat, Jul 4
BOS - Chicago
Boston (BOS) - Chicago (ORD)
$226
$149
One-way
Biggest price drops on these dates for flights from Boston to Chicago
Jun 17 - Jun 18
$393 → $257
35%
Oct 7 - Oct 14
$283 → $171
40%
Aug 25 - Aug 26
$272 → $169
38%
Oct 17 - Oct 19
$293 → $190
35%
Popular Airports to fly from Boston to Chicago
Boston - Chicago route insights
💸 Price insights
Recent fares are above the typical level.
Recent fares for Boston to Chicago are above the typical level, with a median price of $248.
📅 Best time to fly
Fly in November for the best prices.
Historically, November is the cheapest month to fly from Boston to Chicago, with a median price of $103.
⏱️ Flight duration
The typical flight duration is 5h 33m.
Flights from Boston to Chicago typically take 5h 33m, covering a distance of 1382 km.
✈️ Airlines & availability
51.6% of recent deals are direct flights.
About half of recent deals for this route are direct, with connecting flights typically having 2 stopovers.
🏆 Airline highlight
JetBlue Airways offers direct flights.
JetBlue Airways is an airline that has offered direct flights on the Boston to Chicago route.
🎯 Booking tip
Deals are frequent for this route.
Deals for flights from Boston to Chicago are frequent, with over 1 deal per day historically.
Boston main airports to depart from
Logan International (BOS)
Logan International Airport is a convenient option for flights from Boston to Chicago, offering competitive prices.
📍 ~5 km from Boston (reachable by car or public transport)
💸 Flights from ~$127
Chicago main airports to arrive at
O Hare International (ORD)
O'Hare International Airport is a good option for flights from Boston to Chicago, often offering competitive prices.
📍 ~25 km from Chicago city center (reachable by car, train, bus)
💸 Flights from ~$127
Chicago Midway International (MDW)
Chicago Midway International Airport provides another convenient arrival choice for your trip from Boston to Chicago.
📍 ~15 km from Chicago city center (reachable by car, train, bus)
💸 Flights from ~$142
Chicago Rockford International (RFD)
Chicago Rockford International Airport serves as an alternative arrival point for flights to the Chicago area.
📍 ~120 km from Chicago city center (reachable by car)
💸 Flights from ~$258
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
General Mitchell International Airport (MKE) is a useful alternative with high-frequency flight options and direct rail access.
📍 ~135 km from Chicago (reachable by car or train)
💸 Flights from ~$196
South Bend International (SBN)
South Bend International Airport (SBN) is a close alternative, directly connected to downtown Chicago via commuter rail.
📍 ~135 km from Chicago (reachable by car or train)
💸 Flights from ~$211
Gerald R. Ford International (GRR)
Gerald R. Ford International Airport (GRR) is a major regional hub, good for travelers on Chicago's eastern side.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$94
Dane County Regional (MSN)
Dane County Regional Airport (MSN) offers reliable regional service and is less congested than major Chicago airports.
📍 ~205 km from Chicago (reachable by car)
💸 Flights from ~$284
Fort Wayne International (FWA)
Fort Wayne International Airport (FWA) is an alternative for travelers in Chicago's southeastern suburbs.
📍 ~240 km from Chicago (reachable by car)
💸 Flights from ~$308
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from Boston to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From BOS
Elite
Aug 03
Chicago, United States
83% AI deal score
$2,139
$540
Save $1,599
From BOS
Elite
Jun 22
Chicago, United States
82% AI deal score
$2,156
$589
Save $1,567
From BOS
Elite
Jun 17
Chicago, United States
82% AI deal score
$2,241
$605
Save $1,636
From BOS
Elite
Sep 04
Chicago, United States
82% AI deal score
$961
$495
Save $466
From BOS
Elite
Sep 03
Chicago, United States
81% AI deal score
$946
$495
Save $451
From BOS
Elite
Aug 04
Chicago, United States
80% AI deal score
$892
$480
Save $412
From BOS
Elite
Aug 04
Chicago, United States
80% AI deal score
$929
$480
Save $449
From BOS
Elite
Sep 08
Chicago, United States
80% AI deal score
$935
$511
Save $424
From BOS
Elite
Sep 10
Chicago, United States
80% AI deal score
$989
$545
Save $444
From BOS
Elite
Aug 05
Chicago, United States
79% AI deal score
$682
$449
Save $233
From BOS
Elite
Aug 05
Chicago, United States
79% AI deal score
$854
$480
Save $374
From BOS
Elite
Jun 29
Chicago, United States
79% AI deal score
$843
$497
Save $346
From BOS
Elite
Aug 06
Chicago, United States
79% AI deal score
$1,020
$534
Save $486
From BOS
Elite
Jun 17
Chicago, United States
79% AI deal score
$1,743
$575
Save $1,168
From BOS
Elite
Sep 09
Chicago, United States
79% AI deal score
$935
$535
Save $400
From BOS
Elite
Jul 15
Chicago, United States
78% AI deal score
$650
$449
Save $201
From BOS
Elite
Jul 14
Chicago, United States
78% AI deal score
$650
$457
Save $193
From BOS
Elite
Jul 11
Chicago, United States
78% AI deal score
$650
$459
Save $191
From BOS
Elite
Aug 02
Chicago, United States
78% AI deal score
$774
$485
Save $289
From BOS
Elite
Jul 07
Chicago, United States
77% AI deal score
$609
$449
Save $160
From BOS
Elite
Jul 21
Chicago, United States
77% AI deal score
$587
$449
Save $138
From BOS
Elite
Aug 05
Chicago, United States
77% AI deal score
$612
$459
Save $153
From BOS
Elite
Aug 12
Chicago, United States
77% AI deal score
$602
$459
Save $143
From BOS
Elite
Aug 19
Chicago, United States
77% AI deal score
$771
$485
Save $286
From BOS
Elite
Aug 22
Chicago, United States
77% AI deal score
$778
$487
Save $291
From BOS
Elite
Aug 21
Chicago, United States
77% AI deal score
$793
$493
Save $300
From BOS
Elite
Aug 23
Chicago, United States
77% AI deal score
$784
$495
Save $289
From BOS
Elite
Aug 28
Chicago, United States
77% AI deal score
$779
$503
Save $276
From BOS
Elite
Aug 05
Chicago, United States
77% AI deal score
$767
$507
Save $260
From BOS
Elite
Aug 04
Chicago, United States
76% AI deal score
$679
$457
Save $222
From BOS
Elite
Sep 04
Chicago, United States
76% AI deal score
$595
$457
Save $138
From BOS
Elite
Jul 22
Chicago, United States
76% AI deal score
$591
$459
Save $132
From BOS
Elite
Aug 25
Chicago, United States
76% AI deal score
$594
$459
Save $135
From BOS
Elite
Jul 14
Chicago, United States
76% AI deal score
$587
$459
Save $128
From BOS
Elite
Jul 14
Chicago, United States
76% AI deal score
$587
$459
Save $128
From BOS
Elite
Jul 15
Chicago, United States
76% AI deal score
$587
$459
Save $128
From BOS
Elite
Jun 21
Chicago, United States
76% AI deal score
$1,213
$577
Save $636
From BOS
Elite
Jul 02
Chicago, United States
76% AI deal score
$1,098
$652
Save $446
From BOS
Elite
Jul 15
Chicago, United States
76% AI deal score
$625
$487
Save $138
From BOS
Elite
Jul 10
Chicago, United States
76% AI deal score
$640
$503
Save $137
From BOS
Elite
Aug 04
Chicago, United States
75% AI deal score
$644
$449
Save $195
From BOS
Elite
Aug 04
Chicago, United States
75% AI deal score
$637
$457
Save $180
From BOS
Elite
Aug 04
Chicago, United States
75% AI deal score
$645
$457
Save $188
From BOS
Elite
Aug 04
Chicago, United States
75% AI deal score
$644
$457
Save $187
From BOS
Elite
Aug 05
Chicago, United States
75% AI deal score
$675
$457
Save $218
From BOS
Elite
Aug 05
Chicago, United States
75% AI deal score
$654
$457
Save $197
From BOS
Elite
Jul 22
Chicago, United States
75% AI deal score
$558
$459
Save $99
From BOS
Elite
Aug 03
Chicago, United States
75% AI deal score
$722
$480
Save $242
From BOS
Elite
Oct 27
Chicago, United States
75% AI deal score
$789
$517
Save $272
From BOS
Elite
Jun 22
Chicago, United States
75% AI deal score
$833
$555
Save $278
From BOS
Elite
Jul 01
Chicago, United States
75% AI deal score
$1,328
$743
Save $585
From BOS
Elite
Jul 13
Chicago, United States
75% AI deal score
$632
$507
Save $125
From BOS
Elite
Aug 05
Chicago, United States
74% AI deal score
$621
$449
Save $172
From BOS
Elite
Aug 05
Chicago, United States
74% AI deal score
$622
$457
Save $165
From BOS
Elite
Aug 05
Chicago, United States
74% AI deal score
$622
$457
Save $165
From BOS
Elite
Aug 03
Chicago, United States
74% AI deal score
$653
$479
Save $174
From BOS
Elite
Aug 03
Chicago, United States
74% AI deal score
$653
$479
Save $174
From BOS
Elite
Aug 03
Chicago, United States
74% AI deal score
$646
$479
Save $167
From BOS
Elite
Sep 01
Chicago, United States
74% AI deal score
$788
$559
Save $229
From BOS
Elite
Aug 03
Chicago, United States
73% AI deal score
$645
$487
Save $158
From BOS
Elite
Aug 03
Chicago, United States
73% AI deal score
$642
$487
Save $155
From BOS
Elite
Aug 03
Chicago, United States
73% AI deal score
$652
$487
Save $165
From BOS
Elite
Aug 03
Chicago, United States
73% AI deal score
$652
$487
Save $165
From BOS
Elite
Aug 27
Chicago, United States
73% AI deal score
$660
$487
Save $173
From BOS
Elite
Aug 06
Chicago, United States
73% AI deal score
$681
$511
Save $170
From BOS
Elite
Aug 06
Chicago, United States
73% AI deal score
$674
$511
Save $163
From BOS
Elite
Jun 30
Chicago, United States
73% AI deal score
$862
$660
Save $202
From BOS
Elite
Aug 28
Chicago, United States
73% AI deal score
$788
$515
Save $273
From BOS
Elite
Aug 06
Chicago, United States
72% AI deal score
$621
$503
Save $118
From BOS
Elite
Aug 28
Chicago, United States
72% AI deal score
$1,287
$795
Save $492
From BOS
Elite
Oct 29
Chicago, United States
70% AI deal score
$629
$507
Save $122
From BOS
Elite
Aug 17
Chicago, United States
69% AI deal score
$771
$595
Save $176
From BOS
Elite
Nov 07
Chicago, United States
68% AI deal score
$667
$565
Save $102
From BOS
Elite
Aug 06
Chicago, United States
67% AI deal score
$611
$511
Save $100
From BOS
Elite
Aug 06
Chicago, United States
67% AI deal score
$621
$511
Save $110
From BOS
Elite
Oct 22
Chicago, United States
67% AI deal score
$639
$512
Save $127
From BOS
Elite
Aug 07
Chicago, United States
67% AI deal score
$674
$538
Save $136
From BOS
Elite
Aug 07
Chicago, United States
67% AI deal score
$653
$538
Save $115
From BOS
Elite
Aug 08
Chicago, United States
67% AI deal score
$673
$538
Save $135
From BOS
Elite
Aug 08
Chicago, United States
67% AI deal score
$666
$538
Save $128
From BOS
Elite
Aug 07
Chicago, United States
67% AI deal score
$688
$546
Save $142
From BOS
Elite
Aug 07
Chicago, United States
67% AI deal score
$681
$546
Save $135
From BOS
Elite
Aug 08
Chicago, United States
67% AI deal score
$678
$546
Save $132
From BOS
Elite
Aug 08
Chicago, United States
67% AI deal score
$679
$546
Save $133
From BOS
Elite
Oct 30
Chicago, United States
67% AI deal score
$1,176
$795
Save $381
From BOS
Elite
Oct 29
Chicago, United States
67% AI deal score
$1,145
$796
Save $349
From BOS
Elite
Oct 23
Chicago, United States
67% AI deal score
$1,179
$823
Save $356
From BOS
Elite
Sep 28
Chicago, United States
66% AI deal score
$594
$502
Save $92
From BOS
Elite
Sep 17
Chicago, United States
66% AI deal score
$596
$507
Save $89
From BOS
Elite
Oct 22
Chicago, United States
66% AI deal score
$638
$517
Save $121
From BOS
Elite
Aug 07
Chicago, United States
66% AI deal score
$621
$538
Save $83
From BOS
Elite
Aug 08
Chicago, United States
66% AI deal score
$645
$546
Save $99
From BOS
Elite
Aug 19
Chicago, United States
66% AI deal score
$1,010
$808
Save $202
From BOS
Elite
Aug 28
Chicago, United States
66% AI deal score
$1,331
$966
Save $365
From BOS
Elite
Jul 17
Chicago, United States
65% AI deal score
$1,239
$952
Save $287
From BOS
Elite
Jun 17
Chicago, United States
65% AI deal score
$1,686
$1,272
Save $414
From BOS
Elite
Aug 08
Chicago, United States
50% AI deal score
$604
$538
Save $66
From BOS
Elite
Aug 07
Chicago, United States
50% AI deal score
$613
$546
Save $67
From BOS
Elite
Aug 07
Chicago, United States
50% AI deal score
$611
$546
Save $65
From BOS
Elite
Sep 18
Chicago, United States
50% AI deal score
$1,029
$796
Save $233