| Chicago, IL → New York City, NY (Metropolitan Area) | 7766 | $191 | United |
| Chicago, IL → Miami, FL (Metropolitan Area) | 5589 | $229 | United |
| Chicago, IL → Orlando, FL | 5100 | $214 | United |
| Chicago, IL → Los Angeles, CA (Metropolitan Area) | 4593 | $313 | United |
| Chicago, IL → Phoenix, AZ | 4348 | $255 | Southwest |
| Chicago, IL → Dallas/Fort Worth, TX | 3521 | $223 | American |
| Chicago, IL → Las Vegas, NV | 3389 | $257 | United |
| Chicago, IL → Washington, DC (Metropolitan Area) | 3214 | $236 | United |
| Chicago, IL → Fort Myers, FL | 3144 | $259 | United |
| Atlanta, GA (Metropolitan Area) → Chicago, IL | 2933 | $211 | Delta |
| Chicago, IL → Tampa, FL (Metropolitan Area) | 2776 | $215 | Southwest |
| Chicago, IL → Denver, CO | 2731 | $210 | United |
| Chicago, IL → San Francisco, CA (Metropolitan Area) | 2728 | $328 | United |
| Boston, MA (Metropolitan Area) → Chicago, IL | 2707 | $178 | United |
| Chicago, IL → Houston, TX | 2646 | $217 | United |
| Chicago, IL → San Diego, CA | 1954 | $226 | United |
| Chicago, IL → Philadelphia, PA | 1480 | $239 | American |
| Chicago, IL → Minneapolis/St. Paul, MN | 1464 | $243 | Delta |
| Austin, TX → Chicago, IL | 1414 | $239 | United |
| Chicago, IL → Seattle, WA | 1384 | $229 | Alaska |
| Chicago, IL → New Orleans, LA | 1217 | $217 | United |
| Chicago, IL → Nashville, TN | 1166 | $237 | Southwest |
| Charlotte, NC → Chicago, IL | 1146 | $211 | American |
| Chicago, IL → Salt Lake City, UT | 962 | $348 | United |
| Chicago, IL → Raleigh/Durham, NC | 849 | $244 | United |
| Chicago, IL → West Palm Beach/Palm Beach, FL | 827 | $310 | United |
| Chicago, IL → Kansas City, MO | 803 | $260 | Southwest |
| Chicago, IL → Detroit, MI | 735 | $265 | Delta |
| Chicago, IL → Cleveland, OH (Metropolitan Area) | 725 | $225 | United |
| Chicago, IL → Sarasota/Bradenton, FL | 710 | $307 | United |
| Chicago, IL → Portland, OR | 637 | $258 | United |
| Chicago, IL → Jacksonville, FL | 630 | $272 | United |
| Chicago, IL → Columbus, OH | 628 | $248 | United |
| Chicago, IL → San Antonio, TX | 596 | $291 | United |
| Chicago, IL → Palm Springs, CA | 587 | $358 | American |
| Chicago, IL → Pittsburgh, PA | 558 | $239 | United |
| Chicago, IL → St. Louis, MO | 539 | $266 | Southwest |
| Charleston, SC → Chicago, IL | 443 | $270 | United |
| Chicago, IL → Cincinnati, OH | 411 | $233 | United |
| Chicago, IL → Hartford, CT | 391 | $288 | United |
| Chicago, IL → Sacramento, CA | 388 | $340 | United |
| Chicago, IL → Savannah, GA | 382 | $280 | United |
| Chicago, IL → Tucson, AZ | 367 | $333 | American |
| Chicago, IL → Memphis, TN | 367 | $255 | American |
| Chicago, IL → Pensacola, FL | 349 | $224 | United |
| Chicago, IL → Omaha, NE | 349 | $247 | United |
| Chicago, IL → Richmond, VA | 303 | $267 | American |
| Chicago, IL → Knoxville, TN | 276 | $225 | United |
| Chicago, IL → Key West, FL | 266 | $336 | United |
| Chicago, IL → Greenville/Spartanburg, SC | 263 | $226 | American |
| Bozeman, MT → Chicago, IL | 261 | $271 | United |
| Chicago, IL → Norfolk, VA (Metropolitan Area) | 261 | $256 | United |
| Birmingham, AL → Chicago, IL | 260 | $289 | American |
| Chicago, IL → Louisville, KY | 248 | $243 | United |
| Chicago, IL → Oklahoma City, OK | 244 | $273 | American |
| Chicago, IL → Panama City, FL | 234 | $243 | American |
| Chicago, IL → Fayetteville, AR | 230 | $236 | American |
| Albuquerque, NM → Chicago, IL | 225 | $291 | United |
| Chicago, IL → El Paso, TX | 218 | $282 | American |
| Chicago, IL → Harrisburg, PA | 217 | $257 | United |
| Chicago, IL → Greensboro/High Point, NC | 213 | $212 | American |