| Chicago, IL → St. Louis, MO | 297 | $605 | $485–$730 | 1–21 hours | 1 day | 297 mi · 1 day · truck in 1–21 hours |
| Chicago, IL → Lexington, KY | 376 | $545 | $440–$645 | 1 hour | 1 day | 376 mi · 1 day · truck in 1 hour |
| Chicago, IL → Pittsburgh, PA | 461 | $520 | $415–$625 | 1–17 hours | 1–2 days | 461 mi · 1–2 days · truck in 1–17 hours |
| Chicago, IL → Lincoln, NE | 523 | $550 | $515–$580 | 1–2 days | 2 days | 523 mi · 2 days · truck in 1–2 days |
| Chicago, IL → Morgantown, WV | 529 | $560 | $430–$690 | 1–46 hours | 2 days | 529 mi · 2 days · truck in 1–46 hours |
| Chicago, IL → Overland Park, KS | 532 | $705 | $530–$875 | 1–5 hours | 2 days | 532 mi · 2 days · truck in 1–5 hours |
| Chicago, IL → Memphis, TN | 534 | $525 | $495–$555 | 1–2 days | 2 days | 534 mi · 2 days · truck in 1–2 days |
| Chicago, IL → Sioux Falls, SD | 571 | $770 | $620–$920 | 1–23 hours | 2 days | 571 mi · 2 days · truck in 1–23 hours |
| Chicago, IL → Huntsville, AL | 581 | $625 | $520–$725 | 1–23 hours | 2 days | 581 mi · 2 days · truck in 1–23 hours |
| Chicago, IL → Fargo, ND | 646 | $925 | $690–$1,155 | 1–46 hours | 2 days | 646 mi · 2 days · truck in 1–46 hours |
| Chicago, IL → Fayetteville, AR | 671 | $770 | $655–$880 | 1–47 hours | 2 days | 671 mi · 2 days · truck in 1–47 hours |
| Chicago, IL → Rockville, MD | 679 | $750 | $620–$880 | 1–23 hours | 2 days | 679 mi · 2 days · truck in 1–23 hours |
| Chicago, IL → Syracuse, NY | 681 | $800 | $585–$1,020 | 1–13 hours | 2 days | 681 mi · 2 days · truck in 1–13 hours |
| Chicago, IL → Charlotte, NC | 752 | $745 | $600–$890 | 1–6 days | 2 days | 752 mi · 2 days · truck in 1–6 days |
| Chicago, IL → Cherry Hill, NJ | 766 | $725 | $600–$850 | 1–3 days | 2 days | 766 mi · 2 days · truck in 1–3 days |
| Chicago, IL → Richmond, VA | 782 | $835 | $655–$1,015 | 1–3 hours | 2 days | 782 mi · 2 days · truck in 1–3 hours |
| Chicago, IL → New York, NY | 792 | $745 | $625–$860 | 1–6 days | 2 days | 792 mi · 2 days · truck in 1–6 days |
| Chicago, IL → Dover, DE | 794 | $770 | $600–$940 | 1–7 days | 2 days | 794 mi · 2 days · truck in 1–7 days |
| Chicago, IL → Oklahoma City, OK | 795 | $780 | $665–$895 | 1–4 days | 2 days | 795 mi · 2 days · truck in 1–4 days |
| Chicago, IL → Stamford, CT | 828 | $860 | $685–$1,030 | 1–18 hours | 2–3 days | 828 mi · 2–3 days · truck in 1–18 hours |
| Chicago Heights, IL → Hampton, VA | 857 | $785 | $630–$945 | 1–2 days | 2–3 days | 857 mi · 2–3 days · truck in 1–2 days |
| Chicago, IL → Rutland, VT | 895 | $1,020 | $770–$1,270 | 1–20 hours | 2–3 days | 895 mi · 2–3 days · truck in 1–20 hours |
| Chicago, IL → Gulfport, MS | 899 | $980 | $795–$1,170 | 1–27 hours | 2–3 days | 899 mi · 2–3 days · truck in 1–27 hours |
| Chicago, IL → Charleston, SC | 916 | $895 | $780–$1,010 | 1–26 hours | 2–3 days | 916 mi · 2–3 days · truck in 1–26 hours |
| Decatur, IL → Hempstead, NY | 926 | $795 | $450–$1,140 | 1–3 days | 2–3 days | 926 mi · 2–3 days · truck in 1–3 days |
| Chicago, IL → New Orleans, LA | 927 | $995 | $745–$1,240 | 1–27 hours | 2–3 days | 927 mi · 2–3 days · truck in 1–27 hours |
| Springfield, IL → New York, NY | 943 | $600 | $475–$720 | 1–3 days | 2–3 days | 943 mi · 2–3 days · truck in 1–3 days |
| Chicago, IL → Worcester, MA | 947 | $945 | $680–$1,210 | 1–16 hours | 2–3 days | 947 mi · 2–3 days · truck in 1–16 hours |
| Chicago, IL → Savannah, GA | 953 | $810 | $640–$985 | 1–4 days | 2–3 days | 953 mi · 2–3 days · truck in 1–4 days |
| Chicago, IL → Dallas, TX | 960 | $945 | $805–$1,080 | 1–3 days | 2–3 days | 960 mi · 2–3 days · truck in 1–3 days |
| Chicago, IL → Tallahassee, FL | 966 | $995 | $670–$1,315 | 1–22 hours | 2–3 days | 966 mi · 2–3 days · truck in 1–22 hours |
| Chicago, IL → Cheyenne, WY | 967 | $965 | $745–$1,180 | 1–3 days | 2–3 days | 967 mi · 2–3 days · truck in 1–3 days |
| Chicago, IL → Warwick, RI | 969 | $950 | $730–$1,170 | 1–6 hours | 2–3 days | 969 mi · 2–3 days · truck in 1–6 hours |
| Chicago, IL → Nashua, NH | 993 | $985 | $790–$1,180 | 1–18 hours | 2–3 days | 993 mi · 2–3 days · truck in 1–18 hours |
| Chicago, IL → Colorado Springs, CO | 1,074 | $960 | $790–$1,125 | 1–15 hours | 3 days | 1,074 mi · 3 days · truck in 1–15 hours |
| Chicago, IL → Orlando, FL | 1,130 | $850 | $745–$955 | 1–21 hours | 3 days | 1,130 mi · 3 days · truck in 1–21 hours |
| Chicago, IL → Austin, TX | 1,155 | $870 | $750–$985 | 1–4 days | 3 days | 1,155 mi · 3 days · truck in 1–4 days |
| Chicago, IL → Bangor, ME | 1,220 | $1,095 | $860–$1,330 | 1–18 hours | 3–4 days | 1,220 mi · 3–4 days · truck in 1–18 hours |
| Springfield, IL → Miami, FL | 1,294 | $815 | $665–$970 | 1–48 hours | 3–4 days | 1,294 mi · 3–4 days · truck in 1–48 hours |
| Chicago, IL → Albuquerque, NM | 1,337 | $1,170 | $1,020–$1,320 | 1–5 days | 3–4 days | 1,337 mi · 3–4 days · truck in 1–5 days |
| Chicago, IL → Missoula, MT | 1,589 | $1,470 | $1,170–$1,770 | 1–2 days | 4 days | 1,589 mi · 4 days · truck in 1–2 days |
| Springfield, IL → Phoenix, AZ | 1,599 | $1,115 | $915–$1,310 | 1–24 hours | 4 days | 1,599 mi · 4 days · truck in 1–24 hours |
| Chicago, IL → St. George, UT | 1,633 | $1,090 | $830–$1,345 | 1–47 hours | 4–5 days | 1,633 mi · 4–5 days · truck in 1–47 hours |
| Aurora, IL → Sierra Vista, AZ | 1,706 | $1,050 | $840–$1,260 | 1–26 hours | 4–5 days | 1,706 mi · 4–5 days · truck in 1–26 hours |
| Chicago, IL → Coeur d'Alene, ID | 1,754 | $1,360 | $1,155–$1,565 | 1–6 days | 4–5 days | 1,754 mi · 4–5 days · truck in 1–6 days |
| Chicago, IL → Tucson, AZ | 1,783 | $1,050 | $865–$1,235 | 1–26 hours | 4–5 days | 1,783 mi · 4–5 days · truck in 1–26 hours |
| Markham, IL → Phoenix, AZ | 1,786 | $1,025 | $800–$1,250 | 1–4 days | 4–5 days | 1,786 mi · 4–5 days · truck in 1–4 days |
| Chicago, IL → Spokane, WA | 1,788 | $1,360 | $1,155–$1,565 | 1–6 days | 4–5 days | 1,788 mi · 4–5 days · truck in 1–6 days |
| Chicago, IL → Phoenix, AZ | 1,799 | $1,060 | $825–$1,270 | 1–4 days | 4–5 days | 1,799 mi · 4–5 days · truck in 1–4 days |
| Chicago, IL → Reno, NV | 1,914 | $1,255 | $940–$1,570 | 1–18 hours | 4–5 days | 1,914 mi · 4–5 days · truck in 1–18 hours |
| Chicago, IL → Los Angeles, CA | 2,017 | $1,050 | $935–$1,165 | 1–5 days | 5–6 days | 2,017 mi · 5–6 days · truck in 1–5 days |
| Chicago, IL → Seattle, WA | 2,065 | $1,330 | $1,100–$1,565 | 1–14 hours | 5–6 days | 2,065 mi · 5–6 days · truck in 1–14 hours |
| Chicago, IL → San Francisco, CA | 2,131 | $1,185 | $520–$1,845 | 1–42 hours | 5–6 days | 2,131 mi · 5–6 days · truck in 1–42 hours |
| Chicago, IL → Eugene, OR | 2,167 | $1,330 | $1,130–$1,535 | 1–7 days | 5–6 days | 2,167 mi · 5–6 days · truck in 1–7 days |