Cheap Flights from Chicago

405 deals departing from Chicago

Denver skyline with Rocky Mountains
Save 59%
$88
$213
Chicago skyline and Lake Michigan
ORDDEN
Chicago to Denver
Frontier Airlines
Nonstop·round trip
May 23 – May 26
Denver skyline with Rocky Mountains
Save 57%
$80
$184
Chicago skyline and Lake Michigan
ORDDEN
Chicago to Denver
Frontier Airlines
Nonstop·round trip
May 9 – May 11
Los Angeles skyline at dusk
Save 56%
$102
$223
Chicago skyline and Lake Michigan
ORDLAX
Chicago to Los Angeles
Frontier Airlines
Nonstop·round trip
Apr 26 – Apr 29
Austin skyline and Congress Avenue Bridge
Save 53%
$122
$258
Chicago skyline and Lake Michigan
ORDAUS
Chicago to Austin
Frontier Airlines
Nonstop·round trip
Apr 8 – Apr 12Last Chance
Philadelphia skyline with City Hall
Save 53%
$129
$219
Chicago skyline and Lake Michigan
ORDPHL
Chicago to Philadelphia
Frontier Airlines
Nonstop·round trip
Apr 14 – Apr 23
Columbus Ohio skyline
Save 53%
$150
$319
Chicago skyline and Lake Michigan
ORDCMH
Chicago to Columbus
Frontier Airlines
Nonstop·round trip
May 13 – May 17
Old San Juan Puerto Rico colorful buildings
Save 51%
$173
$356
Chicago skyline and Lake Michigan
ORDSJU
Chicago to San Juan
Frontier Airlines
Nonstop·round trip
Apr 26 – Apr 30
Orlando Lake Eola skyline at night
Save 49%
$107
$200
Chicago skyline and Lake Michigan
ORDORL
Chicago to Orlando
Spirit Airlines
Nonstop·round trip
Apr 29 – May 7
Houston Texas skyline
Save 48%
$72
$139
Chicago skyline and Lake Michigan
ORDHOU
Chicago to Houston
Frontier Airlines
Nonstop·round trip
Jun 10 – Jun 14
Bali Ulun Danu Beratan temple
Save 46%
$726
$1349
Chicago skyline and Lake Michigan
ORDDPS
Chicago to Denpasar (Bali)
Air India
Nonstop·round trip
Oct 12 – Oct 22
BGW
Baghdad
Save 46%
$870
$1617
Chicago skyline and Lake Michigan
ORDBGW
Chicago to Baghdad
Qatar Airways
Nonstop·round trip
Aug 14 – Sep 7
Las Vegas Strip with Bellagio fountains
Save 45%
$109
$198
Chicago skyline and Lake Michigan
ORDLAS
Chicago to Las Vegas
Frontier Airlines
Nonstop·round trip
Apr 21 – Apr 24
MLM
Morelia
Save 45%
$252
$459
Chicago skyline and Lake Michigan
ORDMLM
Chicago to Morelia
Volaris
Nonstop·round trip
Apr 17 – Apr 26
Fort Myers aerial with Caloosahatchee River
Save 44%
$171
$306
Chicago skyline and Lake Michigan
ORDFMY
Chicago to Fort Myers
Frontier Airlines
Nonstop·round trip
Apr 25 – May 2
Old San Juan Puerto Rico colorful buildings
Save 44%
$199
$356
Chicago skyline and Lake Michigan
ORDSJU
Chicago to San Juan
Spirit Airlines
Nonstop·round trip
May 21 – May 25
Atlanta skyline at sunset
Save 43%
$65
$115
Chicago skyline and Lake Michigan
ORDATL
Chicago to Atlanta
Frontier Airlines
Nonstop·round trip
May 27 – Jun 1
Miami Beach oceanfront
Save 42%
$67
$116
Chicago skyline and Lake Michigan
ORDMIA
Chicago to Miami
Frontier Airlines
Nonstop·round trip
Apr 12 – Apr 17Ending Soon
Cancun turquoise beach and resorts
Save 42%
$218
$377
Chicago skyline and Lake Michigan
ORDCUN
Chicago to Cancun
Volaris
Nonstop·round trip
Jul 10 – Jul 16
Boston skyline and harbor
Save 40%
$147
$244
Chicago skyline and Lake Michigan
ORDBOS
Chicago to Boston
JetBlue Airways
Nonstop·round trip
May 7 – May 10
Guatemala City Metropolitan Cathedral
Save 40%
$213
$354
Chicago skyline and Lake Michigan
ORDGUA
Chicago to Guatemala City
Avianca
Nonstop·round trip
Jun 6 – Jun 15
Sao Paulo skyline
Save 40%
$633
$1053
Chicago skyline and Lake Michigan
ORDSAO
Chicago to Sao Paulo
Arajet
Nonstop·round trip
Aug 10 – Aug 22
Baltimore Inner Harbor at night
Save 39%
$145
$236
Chicago skyline and Lake Michigan
ORDBWI
Chicago to Baltimore
Frontier Airlines
Nonstop·round trip
Apr 30 – May 2
STT
Saint Thomas
Save 39%
$339
$527
Chicago skyline and Lake Michigan
ORDSTT
Chicago to Saint Thomas
Spirit Airlines
Nonstop·round trip
Apr 26 – Apr 28
Bangkok temples and skyline
Save 39%
$533
$878
Chicago skyline and Lake Michigan
ORDBKK
Chicago to Bangkok
Air India
Nonstop·round trip
Oct 21 – Oct 27
Cancun turquoise beach and resorts
Save 38%
$243
$390
Chicago skyline and Lake Michigan
ORDCUN
Chicago to Cancun
Frontier Airlines
Nonstop·round trip
Apr 17 – Apr 24
Warsaw Old Town and skyline
Save 38%
$423
$678
Chicago skyline and Lake Michigan
ORDWAW
Chicago to Warsaw
Turkish Airlines
Nonstop·round trip
Apr 21 – May 12
Las Vegas Strip with Bellagio fountains
Save 37%
$137
$220
Chicago skyline and Lake Michigan
ORDLAS
Chicago to Las Vegas
Frontier Airlines
Nonstop·round trip
May 3 – May 9
Frankfurt Romerberg square with Justice statue
Save 37%
$684
$800
Chicago skyline and Lake Michigan
ORDFRA
Chicago to Frankfurt
Icelandair
Nonstop·round trip
Apr 21 – May 12
Tampa skyline and waterfront
Save 36%
$138
$215
Chicago skyline and Lake Michigan
ORDTPA
Chicago to Tampa
Spirit Airlines
Nonstop·round trip
Apr 22 – Apr 25
SJD
San Jose del Cabo
Save 36%
$269
$423
Chicago skyline and Lake Michigan
ORDSJD
Chicago to San Jose del Cabo
Volaris
Nonstop·round trip
May 2 – May 6
TIA
Tirana
Save 35%
$548
$848
Chicago skyline and Lake Michigan
ORDTIA
Chicago to Tirana
Turkish Airlines
Nonstop·round trip
Apr 13 – Apr 23
Dallas skyline aerial view
Save 34%
$95
$143
Chicago skyline and Lake Michigan
ORDDFW
Chicago to Dallas
Spirit Airlines
Nonstop·round trip
May 3 – May 3
CTG
Cartagena
Save 34%
$241
$367
Chicago skyline and Lake Michigan
ORDCTG
Chicago to Cartagena
American Airlines
Nonstop·round trip
Jun 7 – Jun 11
Istanbul Blue Mosque and Bosphorus
Save 34%
$620
$934
Chicago skyline and Lake Michigan
ORDIST
Chicago to Istanbul
Etihad Airways
Nonstop·round trip
Apr 20 – May 12
Mexico City Palacio de Bellas Artes
Save 33%
$157
$236
Chicago skyline and Lake Michigan
ORDMEX
Chicago to Mexico City
Volaris
Nonstop·round trip
Apr 8 – Apr 9Last Chance
Puerto Vallarta beach and hillside
Save 33%
$380
$568
Chicago skyline and Lake Michigan
ORDPVR
Chicago to Puerto Vallarta
Volaris
Nonstop·round trip
Oct 8 – Oct 15
BAK
Baku
Save 33%
$780
$1166
Chicago skyline and Lake Michigan
ORDBAK
Chicago to Baku
Turkish Airlines
Nonstop·round trip
Nov 12 – Dec 4
Miami Beach oceanfront
Save 32%
$79
$116
Chicago skyline and Lake Michigan
ORDMIA
Chicago to Miami
Spirit Airlines
Nonstop·round trip
Apr 10 – Apr 14Ending Soon
Orlando Lake Eola skyline at night
Save 32%
$114
$167
Chicago skyline and Lake Michigan
ORDORL
Chicago to Orlando
Frontier Airlines
Nonstop·round trip
Apr 17 – Apr 21
Phoenix skyline with desert mountains
Save 32%
$122
$179
Chicago skyline and Lake Michigan
ORDPHX
Chicago to Phoenix
Frontier Airlines
Nonstop·round trip
Apr 13 – Apr 18
TIA
Tirana
Save 32%
$560
$827
Chicago skyline and Lake Michigan
ORDTIA
Chicago to Tirana
Turkish Airlines
Nonstop·round trip
Aug 27 – Sep 23
RMO
Chisinau
Save 32%
$568
$835
Chicago skyline and Lake Michigan
ORDRMO
Chicago to Chisinau
Turkish Airlines
Nonstop·round trip
Sep 25 – Oct 15
Vienna Schonbrunn Palace
Save 32%
$718
$1058
Chicago skyline and Lake Michigan
ORDVIE
Chicago to Vienna
Turkish Airlines
Nonstop·round trip
Apr 9 – May 27Last Chance
Mexico City Palacio de Bellas Artes
Save 31%
$164
$236
Chicago skyline and Lake Michigan
ORDMEX
Chicago to Mexico City
Volaris
Nonstop·round trip
Apr 28 – May 5
Memphis Beale Street and skyline
Save 30%
$181
$257
Chicago skyline and Lake Michigan
ORDMEM
Chicago to Memphis
United Airlines
Nonstop·round trip
Apr 7 – Apr 8Departs Tomorrow
Fort Myers aerial with Caloosahatchee River
Save 30%
$200
$286
Chicago skyline and Lake Michigan
ORDFMY
Chicago to Fort Myers
American Airlines
Nonstop·round trip
May 5 – May 12
Mexico City Palacio de Bellas Artes
$168
$236
Chicago skyline and Lake Michigan
ORDMEX
Chicago to Mexico City
Volaris
Nonstop·round trip
May 29 – Jun 7
Seattle skyline with Space Needle and Mount Rainier
$172
$241
Chicago skyline and Lake Michigan
ORDSEA
Chicago to Seattle
Alaska Airlines
Nonstop·round trip
May 28 – May 31
San Diego skyline and Coronado Bridge
$276
Chicago skyline and Lake Michigan
ORDSAN
Chicago to San Diego
Alaska Airlines
Nonstop·round trip
May 1 – May 5
Sarasota Florida coastline
$361
$412
Chicago skyline and Lake Michigan
ORDSRQ
Chicago to Sarasota
American Airlines
Nonstop·round trip
May 20 – May 27
View all 405 deals