Woven Adventures

Cheap Flights to Chicago

183 deals to Chicago

Chicago skyline and Lake Michigan
Save 50%
$180
$244
Ontario California aerial with San Gabriel Mountains
ONTCHI
Ontario to Chicago
Southwest Airlines
Nonstop·round trip
Sep 2 – Sep 4
Chicago skyline and Lake Michigan
Save 48%
$102
$198
Fort Lauderdale beach aerial
FLLCHI
Fort Lauderdale to Chicago
Frontier Airlines
Nonstop·round trip
Oct 2 – Oct 5
Chicago skyline and Lake Michigan
Save 47%
$201
$378
Oakland skyline and Bay Bridge
OAKCHI
Oakland to Chicago
Southwest Airlines
Nonstop·round trip
Jul 31 – Aug 4
Chicago skyline and Lake Michigan
Save 43%
$126
$221
New York City skyline from New Jersey
EWRCHI
Newark to Chicago
Frontier Airlines
Nonstop·round trip
Aug 28 – Aug 30
Chicago skyline and Lake Michigan
Save 41%
$110
$188
Dallas skyline aerial view
DFWCHI
Dallas to Chicago
Frontier Airlines
Nonstop·round trip
Sep 5 – Sep 9
Chicago skyline and Lake Michigan
Save 41%
$166
$282
Dallas Texas skyline
DALCHI
DAL to Chicago
Southwest Airlines
Nonstop·round trip
Nov 26 – Nov 30
Chicago skyline and Lake Michigan
Save 40%
$120
$201
Atlanta skyline at sunset
ATLCHI
Atlanta to Chicago
Frontier Airlines
Nonstop·round trip
Jul 19 – Jul 22Departs Tomorrow
Chicago skyline and Lake Michigan
Save 39%
$133
$218
Tampa skyline and waterfront
TPACHI
Tampa to Chicago
Allegiant Air
Nonstop·round trip
Jul 20 – Aug 24Last Chance
Chicago skyline and Lake Michigan
Save 39%
$159
$261
Los Angeles skyline at dusk
LAXCHI
Los Angeles to Chicago
Frontier Airlines
Nonstop·round trip
Aug 20 – Aug 23
Chicago skyline and Lake Michigan
Save 39%
$191
$313
San Diego skyline and Coronado Bridge
SANCHI
San Diego to Chicago
United Airlines
Nonstop·round trip
Aug 1 – Aug 8
Chicago skyline and Lake Michigan
Save 38%
$110
$176
Los Angeles skyline at dusk
LAXCHI
Los Angeles to Chicago
Frontier Airlines
Nonstop·round trip
Aug 18 – Aug 19
Chicago skyline and Lake Michigan
Save 37%
$141
$223
Baltimore Inner Harbor at night
BWICHI
Baltimore to Chicago
Frontier Airlines
Nonstop·round trip
Oct 8 – Oct 13
Chicago skyline and Lake Michigan
Save 37%
$146
$233
Dallas Texas skyline
DALCHI
DAL to Chicago
Southwest Airlines
Nonstop·round trip
Aug 8 – Aug 14
Chicago skyline and Lake Michigan
Save 36%
$123
$191
Manhattan skyline from above
LGACHI
New York to Chicago
Frontier Airlines
Nonstop·round trip
Aug 28 – Aug 30
Chicago skyline and Lake Michigan
Save 36%
$123
$191
Manhattan skyline from above
LGACHI
New York to Chicago
Southwest Airlines
Nonstop·round trip
Aug 28 – Aug 30
Chicago skyline and Lake Michigan
Save 36%
$165
$259
Orlando Lake Eola skyline at night
MCOCHI
Orlando to Chicago
Frontier Airlines
Nonstop·round trip
Jul 31 – Aug 3
Chicago skyline and Lake Michigan
Save 35%
$215
$331
San Jose downtown skyline
SJCCHI
San Jose to Chicago
Southwest Airlines
Nonstop·round trip
Jul 30 – Aug 4
Chicago skyline and Lake Michigan
Save 34%
$133
$201
Philadelphia skyline with City Hall
PHLCHI
Philadelphia to Chicago
Frontier Airlines
Nonstop·round trip
Sep 21 – Sep 25
Chicago skyline and Lake Michigan
Save 34%
$145
$221
New York City skyline from New Jersey
EWRCHI
Newark to Chicago
United Airlines
Nonstop·round trip
Aug 28 – Aug 31
Chicago skyline and Lake Michigan
Save 33%
$320
$481
San Jose downtown skyline
SJCCHI
San Jose to Chicago
Southwest Airlines
Nonstop·round trip
Jul 29 – Aug 4
Chicago skyline and Lake Michigan
Save 33%
$323
$481
San Jose downtown skyline
SJCCHI
San Jose to Chicago
Alaska Airlines
Nonstop·round trip
Jul 30 – Aug 3
Chicago skyline and Lake Michigan
Save 32%
$121
$177
Dallas skyline aerial view
DFWCHI
Dallas to Chicago
Frontier Airlines
Nonstop·round trip
Aug 8 – Aug 14
Chicago skyline and Lake Michigan
Save 32%
$124
$182
Los Angeles skyline at dusk
LAXCHI
Los Angeles to Chicago
Southwest Airlines
Nonstop·round trip
Sep 1 – Sep 3
Chicago skyline and Lake Michigan
Save 32%
$322
$473
Laguna Beach Orange County California
SNACHI
Santa Ana to Chicago
Alaska Airlines
Nonstop·round trip
Dec 25 – Jan 9
Chicago skyline and Lake Michigan
Save 31%
$170
$246
Los Angeles skyline at dusk
LAXCHI
Los Angeles to Chicago
Frontier Airlines
Nonstop·round trip
Sep 29 – Oct 7
Chicago skyline and Lake Michigan
Save 30%
$128
$182
Fort Lauderdale beach aerial
FLLCHI
Fort Lauderdale to Chicago
Allegiant Air
Nonstop·round trip
Aug 6 – Sep 8
Chicago skyline and Lake Michigan
Save 30%
$159
$226
Orlando Lake Eola skyline at night
MCOCHI
Orlando to Chicago
Frontier Airlines
Nonstop·round trip
Sep 25 – Sep 28
Chicago skyline and Lake Michigan
Save 30%
$312
$444
Oakland skyline and Bay Bridge
OAKCHI
Oakland to Chicago
Alaska Airlines
Nonstop·round trip
Jul 30 – Aug 3
Chicago skyline and Lake Michigan
$159
$239
Louisville Kentucky skyline
SDFCHI
Louisville to Chicago
Southwest Airlines
Nonstop·round trip
Aug 18 – Aug 31
Chicago skyline and Lake Michigan
$149
$206
Minneapolis skyline with Stone Arch Bridge
MSPCHI
Minneapolis to Chicago
Sun Country Airlines
Nonstop·round trip
Nov 6 – Nov 26
Chicago skyline and Lake Michigan
$177
$245
Denver skyline with Rocky Mountains
DENCHI
Denver to Chicago
Frontier Airlines
Nonstop·round trip
Jul 31 – Aug 9
Chicago skyline and Lake Michigan
$191
$266
San Francisco Golden Gate Bridge
SFOCHI
San Francisco to Chicago
Southwest Airlines
Nonstop·round trip
Jul 30 – Aug 4
Chicago skyline and Lake Michigan
$184
$245
Denver skyline with Rocky Mountains
DENCHI
Denver to Chicago
Southwest Airlines
Nonstop·round trip
Aug 1 – Aug 9
Chicago skyline and Lake Michigan
$239
$313
San Diego skyline and Coronado Bridge
SANCHI
San Diego to Chicago
Alaska Airlines
Nonstop·round trip
Aug 1 – Aug 8
Chicago skyline and Lake Michigan
$369
$484
Laguna Beach Orange County California
SNACHI
Santa Ana to Chicago
Alaska Airlines
Nonstop·round trip
Sep 23 – Sep 30
Chicago skyline and Lake Michigan
$588
$758
Honolulu Waikiki Beach and Diamond Head
HNLCHI
Honolulu to Chicago
Southwest Airlines
Nonstop·round trip
Aug 24 – Aug 31
Chicago skyline and Lake Michigan
$284
$356
Rochester New York High Falls at sunset
ROCCHI
Rochester to Chicago
JetBlue Airways
Nonstop·round trip
Aug 12 – Aug 15
Chicago skyline and Lake Michigan
$383
$481
San Jose downtown skyline
SJCCHI
San Jose to Chicago
Alaska Airlines
Nonstop·round trip
Jul 29 – Aug 3
Chicago skyline and Lake Michigan
$319
$383
Norfolk Virginia harbor with red-sailed schooner
ORFCHI
Norfolk to Chicago
Breeze Airways
Nonstop·round trip
Sep 10 – Sep 15
Chicago skyline and Lake Michigan
$150
$195
Minneapolis skyline with Stone Arch Bridge
MSPCHI
Minneapolis to Chicago
Sun Country Airlines
Nonstop·round trip
Jul 28 – Aug 1
Chicago skyline and Lake Michigan
$174
$208
Orlando Lake Eola skyline at night
MCOCHI
Orlando to Chicago
Spirit Airlines
Nonstop·round trip
Aug 23 – Sep 1
Chicago skyline and Lake Michigan
$155
$178
Tampa skyline and waterfront
TPACHI
Tampa to Chicago
Allegiant Air
Nonstop·round trip
Nov 13 – Nov 17
Chicago skyline and Lake Michigan
$131
$248
Houston skyline at sunset
IAHCHI
Houston to Chicago
Frontier Airlines
Nonstop·round trip
Aug 7 – Aug 10
Chicago skyline and Lake Michigan
$668
$758
Honolulu Waikiki Beach and Diamond Head
HNLCHI
Honolulu to Chicago
Southwest Airlines
Nonstop·round trip
Sep 1 – Sep 4
Chicago skyline and Lake Michigan
$225
$252
Baltimore Inner Harbor at night
BWICHI
Baltimore to Chicago
Frontier Airlines
Nonstop·round trip
Aug 3 – Aug 6
Chicago skyline and Lake Michigan
$428
$481
San Jose downtown skyline
SJCCHI
San Jose to Chicago
Southwest Airlines
Nonstop·round trip
Aug 1 – Aug 7
Chicago skyline and Lake Michigan
$180
$199
New York City Manhattan skyline
JFKCHI
New York to Chicago
American Airlines
Nonstop·round trip
Sep 11 – Sep 12
Chicago skyline and Lake Michigan
$376
Oakland skyline and Bay Bridge
OAKCHI
Oakland to Chicago
Southwest Airlines
Nonstop·round trip
Jul 30 – Aug 4
Chicago skyline and Lake Michigan
$433
$478
Laguna Beach Orange County California
SNACHI
Santa Ana to Chicago
American Airlines
Nonstop·round trip
Aug 1 – Aug 5
Chicago skyline and Lake Michigan
$197
$214
Denver skyline with Rocky Mountains
DENCHI
Denver to Chicago
Frontier Airlines
Nonstop·round trip
Sep 4 – Sep 9
View all 183 deals