Woven Adventures

Cheap Flights from Chicago

1169 deals departing from Chicago

Tampa skyline and waterfront
Save 57%
$123
$289
Chicago skyline and Lake Michigan
ORDTPA
Chicago to Tampa
Frontier Airlines
Nonstop·round trip
Jul 21 – Jul 25Ending Soon
Honolulu Waikiki Beach and Diamond Head
Save 57%
$290
$677
Chicago skyline and Lake Michigan
ORDHNL
Chicago to Honolulu
Alaska Airlines
Nonstop·round trip
Oct 20 – Oct 27
PAE
Everett
Save 54%
$166
$360
Chicago skyline and Lake Michigan
ORDPAE
Chicago to Everett
Alaska Airlines
Nonstop·round trip
Aug 17 – Aug 21
Buffalo Sheas Theatre downtown
Save 51%
$133
$270
Chicago skyline and Lake Michigan
ORDBUF
Chicago to Buffalo
Frontier Airlines
Nonstop·round trip
Jul 24 – Jul 26Ending Soon
Honolulu Waikiki Beach and Diamond Head
Save 50%
$298
$595
Chicago skyline and Lake Michigan
ORDHNL
Chicago to Honolulu
Alaska Airlines
Nonstop·round trip
Aug 17 – Aug 21
Tbilisi Narikala fortress and old town
Save 50%
$599
$1188
Chicago skyline and Lake Michigan
ORDTBS
Chicago to Tbilisi
Qatar Airways
Nonstop·round trip
Sep 21 – Oct 18
Sharjah Al Qasba canal and Eye of Emirates
Save 50%
$837
$1659
Chicago skyline and Lake Michigan
ORDSHJ
Chicago to Sharjah
Qatar Airways
Nonstop·round trip
Aug 24 – Aug 28
Zurich old town and lake
Save 48%
$498
$949
Chicago skyline and Lake Michigan
ORDZRH
Chicago to Zurich
SAS Scandinavian
Nonstop·round trip
Feb 12 – Feb 16
Orlando Lake Eola skyline at night
Save 47%
$104
$199
Chicago skyline and Lake Michigan
ORDORL
Chicago to Orlando
Frontier Airlines
Nonstop·round trip
Aug 13 – Aug 17
San Jose downtown skyline
Save 47%
$190
$361
Chicago skyline and Lake Michigan
ORDSJC
Chicago to San Jose
JetHunter
Nonstop·round trip
Aug 1 – Aug 7
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%
$1009
$1617
Chicago skyline and Lake Michigan
ORDBGW
Chicago to Baghdad
Qatar Airways
Nonstop·round trip
Aug 14 – Sep 7
Old San Juan Puerto Rico colorful buildings
Save 45%
$145
$266
Chicago skyline and Lake Michigan
ORDSJU
Chicago to San Juan
American Airlines
Nonstop·round trip
Aug 4 – Aug 11
Mexico City Palacio de Bellas Artes
Save 45%
$243
$317
Chicago skyline and Lake Michigan
ORDMEX
Chicago to Mexico City
Volaris
Nonstop·round trip
Aug 11 – Aug 31
RIX
Riga
Save 45%
$489
$891
Chicago skyline and Lake Michigan
ORDRIX
Chicago to Riga
SAS Scandinavian
Nonstop·round trip
Nov 27 – Nov 29
Fort Lauderdale beach aerial
Save 44%
$137
$243
Chicago skyline and Lake Michigan
ORDFLL
Chicago to Fort Lauderdale
Frontier Airlines
Nonstop·round trip
Jul 22 – Jul 26Ending Soon
Myrtle Beach South Carolina boardwalk
Save 44%
$181
$321
Chicago skyline and Lake Michigan
ORDMYR
Chicago to Myrtle Beach
American Airlines
Nonstop·round trip
Jul 28 – Aug 1
Guadalajara cathedral and downtown
Save 44%
$210
$375
Chicago skyline and Lake Michigan
ORDGDL
Chicago to Guadalajara
Viva Aerobus
Nonstop·round trip
Aug 2 – Aug 3
Los Angeles skyline at dusk
Save 43%
$145
$256
Chicago skyline and Lake Michigan
ORDLAX
Chicago to Los Angeles
Frontier Airlines
Nonstop·round trip
Aug 26 – Sep 2
Budapest Parliament on the Danube at twilight
Save 43%
$528
$933
Chicago skyline and Lake Michigan
ORDBUH
Chicago to Bucharest
United Airlines
Nonstop·round trip
Aug 12 – Aug 26
Denver skyline with Rocky Mountains
Save 42%
$131
$227
Chicago skyline and Lake Michigan
ORDDEN
Chicago to Denver
Frontier Airlines
Nonstop·round trip
Jul 24 – Jul 27Ending Soon
ZNZ
Zanzibar
Save 42%
$1077
$1853
Chicago skyline and Lake Michigan
ORDZNZ
Chicago to Zanzibar
Turkish Airlines
Nonstop·round trip
Oct 7 – Oct 10
Seattle skyline with Space Needle and Mount Rainier
Save 41%
$164
$278
Chicago skyline and Lake Michigan
ORDSEA
Chicago to Seattle
Alaska Airlines
Nonstop·round trip
Aug 17 – Aug 21
Mexico City Palacio de Bellas Artes
Save 41%
$188
$317
Chicago skyline and Lake Michigan
ORDMEX
Chicago to Mexico City
Volaris
Nonstop·round trip
Oct 28 – Nov 4
Montego Bay Jamaica resort aerial
Save 41%
$204
$312
Chicago skyline and Lake Michigan
ORDMBJ
Chicago to Montego Bay
American Airlines
Nonstop·round trip
Aug 27 – Sep 1
Old San Juan Puerto Rico colorful buildings
Save 41%
$222
$379
Chicago skyline and Lake Michigan
ORDSJU
Chicago to San Juan
Frontier Airlines
Nonstop·round trip
Jul 19 – Jul 27Departs Tomorrow
Istanbul Blue Mosque and Bosphorus
Save 41%
$597
$1008
Chicago skyline and Lake Michigan
ORDIST
Chicago to Istanbul
Qatar Airways
Nonstop·round trip
Aug 22 – Sep 4
Tampa skyline and waterfront
Save 40%
$172
$289
Chicago skyline and Lake Michigan
ORDTPA
Chicago to Tampa
American Airlines
Nonstop·round trip
Jul 21 – Jul 25Ending Soon
Budapest Parliament on the Danube at twilight
Save 40%
$563
$933
Chicago skyline and Lake Michigan
ORDBUH
Chicago to Bucharest
Lufthansa
Nonstop·round trip
Aug 13 – Aug 26
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
Tbilisi Narikala fortress and old town
Save 40%
$784
$1314
Chicago skyline and Lake Michigan
ORDTBS
Chicago to Tbilisi
Qatar Airways
Nonstop·round trip
Sep 10 – Oct 28
Myrtle Beach South Carolina boardwalk
Save 39%
$197
$321
Chicago skyline and Lake Michigan
ORDMYR
Chicago to Myrtle Beach
United Airlines
Nonstop·round trip
Jul 28 – Aug 1
Honolulu Waikiki Beach and Diamond Head
Save 39%
$381
$629
Chicago skyline and Lake Michigan
ORDHNL
Chicago to Honolulu
Alaska Airlines
Nonstop·round trip
Aug 4 – Aug 14
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
Sharjah Al Qasba canal and Eye of Emirates
Save 39%
$1006
$1659
Chicago skyline and Lake Michigan
ORDSHJ
Chicago to Sharjah
Qatar Airways
Nonstop·round trip
Aug 2 – Aug 8
Guatemala City Metropolitan Cathedral
Save 38%
$234
$379
Chicago skyline and Lake Michigan
ORDGUA
Chicago to Guatemala City
Avianca
Nonstop·round trip
Oct 22 – Nov 4
NBO
Nairobi
Save 38%
$693
$1121
Chicago skyline and Lake Michigan
ORDNBO
Chicago to Nairobi
Etihad Airways
Nonstop·round trip
Aug 6 – Sep 2
KBL
Kabul
Save 38%
$1185
$1916
Chicago skyline and Lake Michigan
ORDKBL
Chicago to Kabul
Etihad Airways
Nonstop·round trip
Jan 1 – Feb 2
Charlotte skyline
Save 37%
$172
$271
Chicago skyline and Lake Michigan
ORDCLT
Chicago to Charlotte
American Airlines
Nonstop·round trip
Jul 25 – Jul 27Ending Soon
Los Angeles skyline at dusk
Save 37%
$174
$276
Chicago skyline and Lake Michigan
ORDLAX
Chicago to Los Angeles
Frontier Airlines
Nonstop·round trip
Jul 23 – Jul 29Ending Soon
SKD
Samarkand
Save 37%
$1139
$1798
Chicago skyline and Lake Michigan
ORDSKD
Chicago to Samarkand
Turkish Airlines
Nonstop·round trip
Aug 16 – Sep 15
Dallas skyline aerial view
Save 36%
$136
$213
Chicago skyline and Lake Michigan
ORDDFW
Chicago to Dallas
Frontier Airlines
Nonstop·round trip
Sep 9 – Sep 12
Las Vegas Strip with Bellagio fountains
Save 36%
$145
$226
Chicago skyline and Lake Michigan
ORDLAS
Chicago to Las Vegas
Alaska Airlines
Nonstop·round trip
Aug 17 – Aug 21
Cancun turquoise beach and resorts
Save 36%
$212
$331
Chicago skyline and Lake Michigan
ORDCUN
Chicago to Cancun
American Airlines
Nonstop·round trip
Aug 8 – Aug 11
Honolulu Waikiki Beach and Diamond Head
Save 36%
$444
$692
Chicago skyline and Lake Michigan
ORDHNL
Chicago to Honolulu
American Airlines
Nonstop·round trip
Sep 15 – Sep 25
Paris Eiffel Tower at sunset
Save 36%
$532
$837
Chicago skyline and Lake Michigan
ORDPAR
Chicago to Paris
United Airlines
Nonstop·round trip
Feb 3 – Feb 5
BJM
Bujumbura
Save 36%
$1089
$1697
Chicago skyline and Lake Michigan
ORDBJM
Chicago to Bujumbura
United Airlines
Nonstop·round trip
Sep 1 – Oct 3
Fort Lauderdale beach aerial
Save 35%
$131
$201
Chicago skyline and Lake Michigan
ORDFLL
Chicago to Fort Lauderdale
Frontier Airlines
Nonstop·round trip
Aug 23 – Aug 29
Ontario California aerial with San Gabriel Mountains
Save 35%
$186
$285
Chicago skyline and Lake Michigan
ORDONT
Chicago to Ontario
Frontier Airlines
Nonstop·round trip
Aug 26 – Sep 2
Guadalajara cathedral and downtown
Save 35%
$197
$284
Chicago skyline and Lake Michigan
ORDGDL
Chicago to Guadalajara
Volaris
Nonstop·round trip
Aug 28 – Sep 23
View all 1169 deals