Cheap flights to Chicago
Round trips from 22 cities to Chicago, United States, from $116. Economy, per person, in USD.
Prices updated
Flights to Chicago by departure city
Cheapest round trip, per person-
San Francisco → Chicago
Nov 3 – 5 · 1 stop
$116
-
Dallas → Chicago
Nov 6 – 8 · 1 stop
$145
-
Phoenix → Chicago
Nov 23 – 28 · 1 stop
$145
-
Philadelphia → Chicago
Oct 17 – 19 · Nonstop
$146
-
Houston → Chicago
Oct 23 – 26 · Nonstop
$148
-
Los Angeles → Chicago
Jan 15 – 22, 2027 · Nonstop
$153
-
San Diego → Chicago
Nov 13 – 15 · 1 stop
$155
-
Miami → Chicago
Oct 16 – 19 · Nonstop
$156
-
Orlando → Chicago
Oct 7 – 14 · 1 stop
$160
-
Tampa → Chicago
Oct 27 – Nov 3 · 1 stop
$167
-
Atlanta → Chicago
Oct 19 – 21 · 1 stop
$169
-
Denver → Chicago
Oct 23 – 26 · Nonstop
$186
-
Las Vegas → Chicago
Dec 26 – Jan 8, 2027 · Nonstop
$222
-
Charlotte → Chicago
Oct 24 – Nov 2 · 1 stop
$231
-
New York → Chicago
Oct 28 – 31 · 1 stop
$231
-
Austin → Chicago
Nov 25 – 30 · 1 stop
$242
-
Portland → Chicago
Oct 22 – 25 · 1 stop
$244
-
Washington → Chicago
Nov 1 – 4 · 1 stop
$266
-
Boston → Chicago
Nov 11 – 15 · Nonstop
$272
-
Toronto → Chicago
Nov 18 – 27 · Nonstop
$278
-
Seattle → Chicago
Nov 4 – 8 · 1 stop
$297
-
Minneapolis → Chicago
Oct 1 – 7 · 1 stop
$341
Cheapest month to fly to Chicago
Lowest round trip per departure month, any of our cities| Month | Cheapest round trip |
|---|---|
| September 2026 | $253 from New York |
| October 2026 | $146 from Philadelphia |
| November 2026 | $116 from San Francisco (cheapest month) |
| December 2026 | $182 from Los Angeles |
| January 2027 | $153 from Los Angeles |
| February 2027 | $169 from Los Angeles |
| March 2027 | $197 from Philadelphia |
| April 2027 | $241 from Atlanta |
| May 2027 | $249 from Philadelphia |
| June 2027 | $403 from Washington |
| July 2027 | $347 from Philadelphia |
Cheapest dates to Chicago
Best date pair from each city-
Nov 3 – 5 from San Francisco · 2 nights$116Book
Frontier Airlines 1 stop -
Nov 6 – 8 from Dallas · 2 nights$145Book
Frontier Airlines 1 stop
-
Nov 23 – 28 from Phoenix · 5 nights$145Book
Frontier Airlines 1 stop
-
Oct 17 – 19 from Philadelphia · 2 nights$146Book
Frontier Airlines Nonstop
-
Oct 23 – 26 from Houston · 3 nights$148Book
Southwest Airlines Nonstop -
Nov 13 – 15 from San Diego · 2 nights$155Book
Frontier Airlines 1 stop
-
Oct 16 – 19 from Miami · 3 nights$156Book
Frontier Airlines Nonstop
-
Oct 7 – 14 from Orlando · 7 nights$160Book
Allegiant Air 1 stop
Prices change often. The booking site shows the final price before you pay.
Things to do in Chicago
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Airport transfer to Chicago
Fixed prices from ORD on KiwitaxiTo see transfer prices here, turn on partner content in .
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Flights to Chicago: questions
Which city has the cheapest flights to Chicago?
Right now it's San Francisco: round trips from $116 (Nov 3 – 5, 1 stop). Next cheapest: Dallas from $145 and Phoenix from $145. We compare 22 departure cities.
What is the cheapest month to fly to Chicago?
November 2026: the cheapest round trip we have found departing that month is $116. The most expensive month in our data is June, where the cheapest round trip is $403. Based on the 11 months ahead we track.
Are there nonstop flights to Chicago?
Yes. We have found nonstop round trips from Philadelphia, Houston, Miami and Los Angeles. The cheapest is $146 from Philadelphia.
More of United States
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Popular destinations
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About these prices
We track round-trip economy fares to Chicago (United States) from the cities listed above using Travelpayouts / Aviasales data, and refresh every route about once a day. The cheapest round trip we've found is $116 from San Francisco. Prices are per person and were correct when found; the final price is set by the airline or booking site when you book.