Chicago

The Windy City

Chicago offers a perfect blend of architectural marvels, cultural attractions, and culinary delights. Explore the towering skyscrapers of the Magnificent Mile, take a scenic stroll along the Lake Michigan shoreline, and immerse yourself in world-class museums like the Art Institute of Chicago. Don’t miss the chance to indulge in deep-dish pizza and catch a game at Wrigley Field.

Cheap flights to Chicago

OriginDeparture atReturn atFind tickets
Miami25 April 20262 May 2026Tickets from 57
Nashville25 June 202628 June 2026Tickets from 69
Fort Lauderdale8 May 202612 May 2026Tickets from 70
New York24 April 202625 April 2026Tickets from 71
Houston14 April 202621 April 2026Tickets from 74
Atlanta3 June 20269 June 2026Tickets from 82
Dallas20 April 202630 April 2026Tickets from 85
Orlando14 May 202620 May 2026Tickets from 110
Kirksville4 July 202612 July 2026Tickets from 117
Tampa2 May 20264 May 2026Tickets from 124
Los Angeles20 May 202625 May 2026Tickets from 124
Raleigh/Durham4 May 202611 May 2026Tickets from 126
Denver30 April 20263 May 2026Tickets from 126
Las Vegas28 April 202630 April 2026Tickets from 138
Myrtle Beach14 April 202621 April 2026Tickets from 143
Boston14 April 202616 April 2026Tickets from 146
Minneapolis28 July 202630 July 2026Tickets from 147
Baltimore23 April 202626 April 2026Tickets from 148
Philadelphia6 May 202610 May 2026Tickets from 149
Saint Louis4 May 202612 May 2026Tickets from 152
Sacramento7 July 202631 July 2026Tickets from 154
Austin1 May 20265 May 2026Tickets from 158
Pittsburgh24 April 202627 April 2026Tickets from 160
El Paso5 May 202611 May 2026Tickets from 160
Ontario20 May 202625 May 2026Tickets from 161
Cincinnati29 April 202629 April 2026Tickets from 168
Charlotte10 May 202613 May 2026Tickets from 169
Dayton8 April 20268 April 2026Tickets from 174
New Haven12 June 202614 June 2026Tickets from 176
Phoenix8 April 202613 April 2026Tickets from 182
Toronto20 April 202623 April 2026Tickets from 182
New Orleans27 August 202631 August 2026Tickets from 191
Washington15 April 202619 April 2026Tickets from 196
Cancun17 April 202624 April 2026Tickets from 197
San Francisco20 April 202623 April 2026Tickets from 199
Richmond1 May 20263 May 2026Tickets from 201
Daytona Beach2 May 202611 May 2026Tickets from 201
San Juan14 May 202618 May 2026Tickets from 203
Salt Lake City20 April 202623 April 2026Tickets from 207
Grand Rapids2 May 202618 May 2026Tickets from 208
Jacksonville9 April 202611 April 2026Tickets from 223
Fort Myers23 April 20267 May 2026Tickets from 229
Newburgh16 April 202619 April 2026Tickets from 230
Seattle15 April 202622 April 2026Tickets from 231
Amarillo22 May 202625 May 2026Tickets from 237
Kansas City17 April 202621 April 2026Tickets from 244
San Jose20 April 202623 April 2026Tickets from 245
Calgary7 May 202611 May 2026Tickets from 246
Long Beach22 June 202626 June 2026Tickets from 249
Cedar Rapids6 May 202611 May 2026Tickets from 250
Columbus23 May 202625 May 2026Tickets from 251
Mexico City29 April 20266 May 2026Tickets from 260
West Palm Beach11 April 202616 April 2026Tickets from 270
Greensboro/High Point3 June 202610 June 2026Tickets from 272
Rochester12 August 202615 August 2026Tickets from 278
Hartford4 June 202612 June 2026Tickets from 279
Cleveland9 April 202612 April 2026Tickets from 280
Greenville18 June 202621 June 2026Tickets from 281
Guadalajara14 April 202616 April 2026Tickets from 287
Charleston8 May 202611 May 2026Tickets from 294
Monterrey18 May 202625 May 2026Tickets from 302
Fayetteville24 April 202627 April 2026Tickets from 305
San Diego21 May 202625 May 2026Tickets from 308
San Antonio28 May 202631 May 2026Tickets from 312
Memphis5 June 20267 June 2026Tickets from 314
Roanoke10 October 202613 October 2026Tickets from 320
Montreal17 April 202619 April 2026Tickets from 321
Winnipeg8 September 202610 September 2026Tickets from 328
Guatemala City25 December 202631 December 2026Tickets from 329
Portland13 June 202618 June 2026Tickets from 329
Chihuahua11 May 202624 May 2026Tickets from 333
Salina10 April 202612 April 2026Tickets from 334
Peoria12 May 202612 May 2026Tickets from 341
Pensacola20 June 20267 July 2026Tickets from 342
Sioux Falls28 July 202630 July 2026Tickets from 346
Des Moines1 May 20264 May 2026Tickets from 346
Vancouver11 June 202614 June 2026Tickets from 347
San Pedro Sula20 October 202611 November 2026Tickets from 366
Norfolk11 June 202614 June 2026Tickets from 391
Bogota6 May 202613 May 2026Tickets from 396
Oakland20 April 202623 April 2026Tickets from 398
Burlington19 April 202626 April 2026Tickets from 400
Managua14 July 202625 July 2026Tickets from 411
Oklahoma City23 July 202627 July 2026Tickets from 412
Durango18 May 202625 May 2026Tickets from 425
Leon/Guanajuato9 May 202618 May 2026Tickets from 428
Ottawa17 July 202620 July 2026Tickets from 429
Westchester County25 June 202630 June 2026Tickets from 431
Allentown25 April 202625 April 2026Tickets from 433
Punta Cana23 September 202627 September 2026Tickets from 434
Halifax22 May 202626 May 2026Tickets from 435
San Luis Potosi29 June 202610 July 2026Tickets from 439
Fayetteville23 July 202626 July 2026Tickets from 444
Tucson16 June 202621 June 2026Tickets from 444
Dublin25 November 202629 November 2026Tickets from 479
Aspen11 February 202713 February 2027Tickets from 484
Redmond8 April 202615 April 2026Tickets from 489
Copenhagen9 June 202616 June 2026Tickets from 492
Stockholm10 May 202617 May 2026Tickets from 496
Montgomery15 April 202619 April 2026Tickets from 505

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