Cheap Flights from Raleigh to Chicago
Browse current best options from Raleigh. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Raleigh
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 Raleigh to Chicago
Explore current cheapest deals departing from Raleigh to Chicago
Round trip
Sort by: Cheapest
August 26 - August 31
RDU - Chicago
$266
$183
Round trip
September 24 - October 19
RDU - Chicago
$223
$187
Round trip
September 23 - October 19
RDU - Chicago
$222
$187
Round trip
September 24 - October 6
RDU - Chicago
$230
$190
Round trip
September 24 - September 29
RDU - Chicago
$258
$190
Round trip
September 24 - October 13
RDU - Chicago
$223
$190
Round trip
September 24 - October 20
RDU - Chicago
$223
$190
Round trip
September 23 - September 29
RDU - Chicago
$253
$194
Round trip
September 23 - October 6
RDU - Chicago
$229
$194
Round trip
September 23 - October 20
RDU - Chicago
$222
$194
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 Raleigh to Chicago
How much is a round trip from Raleigh to Chicago
Regular price: $208 - $273
Prices are currently below the regular range.
The regular price range for flights from Raleigh to Chicago is typically between $208 and $273. The current lowest deal is $183 with Frontier Airlines, for travel from Aug 26 to Aug 31.
now $183
Low $208
High $273
The cheapest time to fly from Raleigh to Chicago
The cheapest month to fly from RDU to CHI is April, with a median price of $139. The most expensive month is December, with a median price of $885. Prices are generally lower from February to October.
April
Flights from $139
December
Flights from $885
Direct flights from Raleigh to Chicago
American Airlines
Last-minute flights going from Raleigh to Chicago
Sat, Jun 20
RDU - Chicago
Raleigh (RDU) - Chicago (MDW)
Frontier Airlines
$413
$342
One-way
Wed, Jul 1
RDU - Chicago
Raleigh (RDU) - Chicago (MDW)
Frontier Airlines
$243
$230
One-way
Wed, Jul 1
RDU - Chicago
Raleigh (RDU) - Chicago (MDW)
Frontier Airlines
$301
$230
One-way
Wed, Jul 1
RDU - Chicago
Raleigh (RDU) - Chicago (MDW)
Frontier Airlines
$300
$258
One-way
Tue, Jul 7
RDU - Chicago
Raleigh (RDU) - Chicago (MDW)
Frontier Airlines
$283
$202
One-way
Tue, Jul 7
RDU - Chicago
Raleigh (RDU) - Chicago (ORD)
American Airlines
$156
$237
One-way
Biggest price drops on these dates for flights from Raleigh to Chicago
Oct 6 - Oct 13
$373 → $208
44%
Oct 8 - Oct 12
$385 → $231
40%
Oct 27 - Oct 31
$390 → $246
37%
Oct 3 - Oct 5
$374 → $231
38%
Popular Airports to fly from Raleigh to Chicago
Raleigh - Chicago route insights
💸 Price insights
Recent fares are above the typical level
Recent fares from Raleigh to Chicago are above the typical level for the past 90 days.
📅 Best time to fly
April is historically the cheapest month to fly
Historically, April is the cheapest month to fly from Raleigh to Chicago, with a median price of $139.
⏱️ Flight duration
Connecting flights take 9h 3m on average
Connecting flights from Raleigh to Chicago typically take 9h 3m, covering a distance of 1016 km.
✈️ Airlines & availability
Connecting flights are dominant on this route
About 23.2% of recent deals are for direct flights. Connecting flights typically have 1 stopover.
🏆 Airline highlight
American Airlines offers direct flights
American Airlines has offered 1 direct flight deal from Raleigh to Chicago recently.
🎯 Booking tip
Deals appear frequently, about 1 per day
Historically, deals from Raleigh to Chicago appear frequently, about 1 per day.
Raleigh main airports to depart from
Raleigh–Durham International (RDU)
Raleigh–Durham International Airport is a good choice for flights from Raleigh to Chicago.
📍 ~20 km from city center (reachable by car)
💸 Flights from ~$183
Chicago main airports to arrive at
Chicago Midway International (MDW)
Chicago Midway International is a convenient arrival airport for flights from Raleigh to Chicago.
📍 ~15 km from Chicago city center (reachable by car)
💸 Flights from ~$190
Chicago Rockford International (RFD)
Chicago Rockford International offers another arrival option for your trip to Chicago from Raleigh.
📍 ~120 km from Chicago city center (reachable by car)
💸 Flights from ~$194
O Hare International (ORD)
O Hare International is a major arrival airport for travelers flying from Raleigh to Chicago.
📍 ~40 km from Chicago city center (reachable by car)
💸 Flights from ~$196
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
This airport is a useful alternative arrival airport for Chicago with high-frequency flight options.
📍 ~135 km from Chicago (reachable by rail)
💸 Flights from ~$247
South Bend International (SBN)
This airport is a useful alternative arrival airport for Chicago due to its close proximity and direct rail link.
📍 ~120 km from Chicago (reachable by rail)
💸 Flights from ~$195
Gerald R. Ford International (GRR)
This airport is a good alternative for travelers on the eastern side of the Chicago metro area.
📍 ~235 km from Chicago (reachable by car)
💸 Flights from ~$205
Dane County Regional (MSN)
This airport is a reliable regional alternative with consistent service and less congestion than major hubs.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$118
Fort Wayne International (FWA)
This airport is an alternative for travelers located in the southeastern Chicago suburbs.
📍 ~235 km from Chicago (reachable by car)
💸 Flights from ~$248
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from Raleigh to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From RDU
Elite
Oct 03
Chicago, United States
77% AI deal score
$1,142
$579
Save $563
From RDU
Elite
Aug 05
Chicago, United States
74% AI deal score
$673
$537
Save $136
From RDU
Elite
Aug 26
Chicago, United States
74% AI deal score
$754
$519
Save $235
From RDU
Elite
Aug 24
Chicago, United States
74% AI deal score
$794
$535
Save $259
From RDU
Elite
Aug 11
Chicago, United States
74% AI deal score
$789
$535
Save $254
From RDU
Elite
Aug 01
Chicago, United States
69% AI deal score
$2,936
$1,775
Save $1,161
From RDU
Elite
Aug 01
Chicago, United States
69% AI deal score
$2,806
$1,775
Save $1,031
From RDU
Elite
Aug 01
Chicago, United States
69% AI deal score
$2,864
$1,775
Save $1,089
From RDU
Elite
Aug 01
Chicago, United States
69% AI deal score
$2,778
$1,780
Save $998
From RDU
Elite
Aug 18
Chicago, United States
69% AI deal score
$658
$537
Save $121
From RDU
Elite
Aug 12
Chicago, United States
69% AI deal score
$661
$537
Save $124
From RDU
Elite
Aug 01
Chicago, United States
68% AI deal score
$2,782
$1,855
Save $927
From RDU
Elite
Aug 31
Chicago, United States
68% AI deal score
$2,609
$1,874
Save $735
From RDU
Elite
Nov 04
Chicago, United States
68% AI deal score
$632
$537
Save $95
From RDU
Elite
Nov 10
Chicago, United States
68% AI deal score
$631
$537
Save $94
From RDU
Elite
Jul 08
Chicago, United States
68% AI deal score
$625
$537
Save $88
From RDU
Elite
Sep 12
Chicago, United States
68% AI deal score
$726
$535
Save $191
From RDU
Elite
Sep 04
Chicago, United States
67% AI deal score
$2,389
$1,858
Save $531
From RDU
Elite
Sep 04
Chicago, United States
67% AI deal score
$2,480
$1,858
Save $622
From RDU
Elite
Aug 25
Chicago, United States
67% AI deal score
$2,559
$1,859
Save $700
From RDU
Elite
Jul 27
Chicago, United States
67% AI deal score
$2,455
$1,861
Save $594
From RDU
Elite
Sep 05
Chicago, United States
67% AI deal score
$2,477
$1,878
Save $599
From RDU
Elite
Aug 05
Chicago, United States
67% AI deal score
$2,896
$2,032
Save $864
From RDU
Elite
Oct 28
Chicago, United States
67% AI deal score
$610
$537
Save $73
From RDU
Elite
Oct 27
Chicago, United States
67% AI deal score
$610
$537
Save $73
From RDU
Elite
Jul 14
Chicago, United States
67% AI deal score
$588
$519
Save $69
From RDU
Elite
Jul 29
Chicago, United States
67% AI deal score
$588
$519
Save $69
From RDU
Elite
Jul 21
Chicago, United States
67% AI deal score
$588
$519
Save $69
From RDU
Elite
Jul 08
Chicago, United States
67% AI deal score
$587
$519
Save $68
From RDU
Elite
Jul 07
Chicago, United States
67% AI deal score
$600
$519
Save $81
From RDU
Elite
Sep 29
Chicago, United States
67% AI deal score
$684
$535
Save $149
From RDU
Elite
Oct 25
Chicago, United States
67% AI deal score
$715
$569
Save $146
From RDU
Elite
Jul 27
Chicago, United States
66% AI deal score
$2,247
$1,856
Save $391
From RDU
Elite
Jul 27
Chicago, United States
66% AI deal score
$2,246
$1,856
Save $390
From RDU
Elite
Jul 27
Chicago, United States
66% AI deal score
$2,250
$1,856
Save $394
From RDU
Elite
Jul 27
Chicago, United States
66% AI deal score
$2,239
$1,861
Save $378
From RDU
Elite
Sep 05
Chicago, United States
66% AI deal score
$2,389
$1,878
Save $511
From RDU
Elite
Jul 13
Chicago, United States
65% AI deal score
$2,168
$1,854
Save $314
From RDU
Elite
Jul 14
Chicago, United States
65% AI deal score
$2,165
$1,854
Save $311
From RDU
Elite
Jul 13
Chicago, United States
65% AI deal score
$2,168
$1,854
Save $314
From RDU
Elite
Jul 13
Chicago, United States
65% AI deal score
$2,168
$1,854
Save $314
From RDU
Elite
Jul 14
Chicago, United States
65% AI deal score
$2,165
$1,854
Save $311
From RDU
Elite
Jul 14
Chicago, United States
65% AI deal score
$2,165
$1,854
Save $311
From RDU
Elite
Jul 14
Chicago, United States
65% AI deal score
$2,165
$1,859
Save $306
From RDU
Elite
Jul 13
Chicago, United States
65% AI deal score
$2,168
$1,859
Save $309
From RDU
Elite
Jul 13
Chicago, United States
65% AI deal score
$2,178
$1,860
Save $318
From RDU
Elite
Jul 14
Chicago, United States
65% AI deal score
$2,178
$1,860
Save $318
From RDU
Elite
Jul 16
Chicago, United States
65% AI deal score
$2,237
$1,909
Save $328
From RDU
Elite
Jul 27
Chicago, United States
65% AI deal score
$2,237
$1,936
Save $301
From RDU
Elite
Sep 29
Chicago, United States
65% AI deal score
$575
$537
Save $38
From RDU
Elite
Nov 18
Chicago, United States
65% AI deal score
$631
$577
Save $54
From RDU
Elite
Jul 16
Chicago, United States
50% AI deal score
$2,142
$1,903
Save $239
From RDU
Elite
Jul 16
Chicago, United States
50% AI deal score
$2,158
$1,903
Save $255
From RDU
Elite
Jul 16
Chicago, United States
50% AI deal score
$2,158
$1,903
Save $255
From RDU
Elite
Jul 16
Chicago, United States
50% AI deal score
$2,158
$1,908
Save $250
From RDU
Elite
Jul 14
Chicago, United States
50% AI deal score
$2,165
$1,934
Save $231
From RDU
Elite
Jul 13
Chicago, United States
50% AI deal score
$2,168
$1,934
Save $234
From RDU
Elite
Jul 27
Chicago, United States
50% AI deal score
$2,254
$1,971
Save $283
From RDU
Elite
Sep 22
Chicago, United States
50% AI deal score
$574
$537
Save $37
From RDU
Elite
Jul 13
Chicago, United States
49% AI deal score
$2,168
$1,969
Save $199
From RDU
Elite
Jul 14
Chicago, United States
49% AI deal score
$2,149
$1,969
Save $180
From RDU
Elite
Jul 06
Chicago, United States
49% AI deal score
$2,173
$1,980
Save $193
From RDU
Elite
Jul 06
Chicago, United States
49% AI deal score
$2,177
$1,980
Save $197
From RDU
Elite
Jul 16
Chicago, United States
49% AI deal score
$2,158
$1,983
Save $175
From RDU
Elite
Jul 16
Chicago, United States
49% AI deal score
$2,164
$2,018
Save $146
From RDU
Elite
Jul 06
Chicago, United States
49% AI deal score
$2,165
$2,026
Save $139
From RDU
Elite
Jul 02
Chicago, United States
49% AI deal score
$2,192
$2,053
Save $139
From RDU
Elite
Sep 16
Chicago, United States
49% AI deal score
$562
$537
Save $25
From RDU
Elite
Dec 11
Chicago, United States
49% AI deal score
$608
$569
Save $39
From RDU
Elite
Jul 02
Chicago, United States
49% AI deal score
$1,219
$1,017
Save $202
From RDU
Elite
Jun 30
Chicago, United States
48% AI deal score
$2,113
$2,024
Save $89
From RDU
Elite
Jun 18
Chicago, United States
48% AI deal score
$1,359
$1,149
Save $210
From RDU
Elite
Nov 20
Chicago, United States
46% AI deal score
$637
From RDU
Elite
Nov 27
Chicago, United States
46% AI deal score
$637
From RDU
Elite
Nov 16
Chicago, United States
45% AI deal score
$679
From RDU
Elite
Dec 06
Chicago, United States
45% AI deal score
$680
From RDU
Elite
Nov 24
Chicago, United States
44% AI deal score
$703
From RDU
Elite
Jul 24
Chicago, United States
42% AI deal score
$1,090
From RDU
Elite
Jul 03
Chicago, United States
42% AI deal score
$738
From RDU
Elite
Jun 18
Chicago, United States
42% AI deal score
$918
From RDU
Elite
Jul 02
Chicago, United States
39% AI deal score
$770
From RDU
Elite
Nov 17
Chicago, United States
39% AI deal score
$862
From RDU
Elite
Oct 29
Chicago, United States
39% AI deal score
$878
From RDU
Elite
Jun 16
Chicago, United States
38% AI deal score
$3,493
From RDU
Elite
Jun 30
Chicago, United States
36% AI deal score
$4,167
From RDU
Elite
Jul 18
Chicago, United States
36% AI deal score
$1,185
From RDU
Elite
Jul 01
Chicago, United States
35% AI deal score
$4,260
From RDU
Elite
Jul 01
Chicago, United States
35% AI deal score
$4,308
From RDU
Elite
Jul 26
Chicago, United States
32% AI deal score
$1,382
From RDU
Elite
Jul 30
Chicago, United States
32% AI deal score
$1,673
From RDU
Elite
Jul 24
Chicago, United States
31% AI deal score
$1,955
From RDU
Elite
Jun 26
Chicago, United States
31% AI deal score
$2,166
From RDU
Elite
Jun 16
Chicago, United States
31% AI deal score
$2,249
From RDU
Elite
Jun 16
Chicago, United States
31% AI deal score
$2,646
From RDU
Elite
Jun 24
Chicago, United States
31% AI deal score
$2,990