Cheap flights to Chicago
Round trips from 23 cities to Chicago, United States, from $103. Economy, per person, in USD.
Prices updated
Flights to Chicago by departure city
Cheapest round trip, per person-
Orlando → Chicago
Jan 14 – 18, 2027 · Nonstop
$103
-
Fort Lauderdale → Chicago
Jan 8 – 10, 2027 · Nonstop
$124
-
Atlanta → Chicago
Dec 5 – 8 · Nonstop
$137
-
Tampa → Chicago
Jan 8 – 10, 2027 · 1 stop
$138
-
Dallas → Chicago
Dec 9 – 16 · 1 stop
$142
-
Houston → Chicago
Dec 2 – 6 · 1 stop
$177
-
Las Vegas → Chicago
Nov 27 – 30 · 1 stop
$191
-
Miami → Chicago
Dec 19 – 21 · 1 stop
$196
-
Philadelphia → Chicago
Dec 10 – 13 · Nonstop
$207
-
New York → Chicago
Dec 2 – 9 · 1 stop
$208
-
Los Angeles → Chicago
Dec 9 – 16 · 1 stop
$225
-
Phoenix → Chicago
Feb 1 – 4, 2027 · Nonstop
$230
-
Charlotte → Chicago
Dec 3 – 5 · 1 stop
$232
-
Ontario → Chicago
Dec 9 – 16 · 1 stop
$236
-
Washington → Chicago
Dec 21 – 24 · Nonstop
$242
-
Baltimore → Chicago
Dec 21 – 24 · Nonstop
$242
-
Toronto → Chicago
Dec 7 – 16 · Nonstop
$252
-
Boston → Chicago
Dec 4 – 6 · 1 stop
$261
-
San Francisco → Chicago
Dec 12 – 19 · 1 stop
$268
-
Seattle → Chicago
Feb 10 – 13, 2027 · Nonstop
$303
-
Denver → Chicago
Nov 18 – 20 · Nonstop
$320
-
San Jose → Chicago
Dec 16 – 18 · 1 stop
$335
-
Oakland → Chicago
Dec 16 – 18 · 1 stop
$353
Cheapest month to fly to Chicago
Lowest round trip per departure month, any of our cities| Month | Cheapest round trip |
|---|---|
| November 2026 | $191 from Las Vegas |
| December 2026 | $137 from Atlanta |
| January 2027 | $103 from Orlando (cheapest month) |
| February 2027 | $214 from Washington |
| March 2027 | $255 from Houston |
| April 2027 | $330 from Dallas |
| May 2027 | $181 from Philadelphia |
| June 2027 | $401 from Houston |
| July 2027 | $344 from New York |
| August 2027 | $399 from San Francisco |
| September 2027 | $367 from New York |
| October 2027 | $760 from New York |
Cheapest dates to Chicago
Best date pair from each city-
Jan 14 – 18, 2027 from Orlando · 4 nights$103Book
Allegiant Air Nonstop -
Jan 8 – 10, 2027 from Fort Lauderdale · 2 nights$124Book
Frontier Airlines Nonstop -
Dec 5 – 8 from Atlanta · 3 nights$137Book
Frontier Airlines Nonstop
-
Jan 8 – 10, 2027 from Tampa · 2 nights$138Book
Frontier Airlines 1 stop
-
Dec 9 – 16 from Dallas · 7 nights$142Book
Frontier Airlines 1 stop
-
Dec 2 – 6 from Houston · 4 nights$177Book
Frontier Airlines 1 stop
-
Nov 27 – 30 from Las Vegas · 3 nights$191Book
Frontier Airlines 1 stop
-
Dec 19 – 21 from Miami · 2 nights$196Book
Frontier Airlines 1 stop
Prices change often. The booking site shows the final price before you pay.
Things to do in Chicago
One Go City pass for Shedd Aquarium, Skydeck Chicago, 360 CHICAGO and more
- All-Inclusive Pass Unlimited Visit as many attractions as you like for 1–5 days from $149 See pass
- Explorer Pass Pick 3–7 of 36 attractions from $109 See pass
- Essentials Pass A few top attractions, chosen as you go from $99 See pass
What the passes include
Go City prices checked Oct 23, 2026; the final price is on Go City. Photo credits. Partner links: we may earn a commission if you book, at no extra cost to you.
Flights to Chicago: questions
Which city has the cheapest flights to Chicago?
Right now it's Orlando: round trips from $103 (Jan 14 – 18, 2027, nonstop). Next cheapest: Fort Lauderdale from $124 and Atlanta from $137. We compare 23 departure cities.
What is the cheapest month to fly to Chicago?
January 2027: the cheapest round trip we have found departing that month is $103. The most expensive month in our data is October, where the cheapest round trip is $760. Based on the 12 months ahead we track.
Are there nonstop flights to Chicago?
Yes. We have found nonstop round trips from Orlando, Fort Lauderdale, Atlanta and Philadelphia. The cheapest is $103 from Orlando.
More of United States
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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 $103 from Orlando. Prices are per person and were correct when found; the final price is set by the airline or booking site when you book.