Labor Day trips from Chicago

Where can you actually afford to go for Labor Day (2027-09-03–2027-09-06) from Chicago? Ask TripThatFits and get ranked destinations with numbers that bind.

Popular from Chicago

• Albuquerque, NM
• Anchorage, AK
• Aspen, CO
• Baltimore, MD
• Birmingham, AL
• Boise, ID
• Boston, MA
• Bozeman, MT
• Buffalo & Niagara Falls, NY
• Burlington, VT
• Charleston, SC
• Charlotte, NC
• Chattanooga, TN
• Cincinnati, OH
• Cleveland, OH
• Colorado Springs, CO
• Columbus, OH
• Dallas–Fort Worth, TX
• Denver, CO
• Destin & 30A, FL
• Detroit, MI
• El Paso, TX
• Gatlinburg & the Smokies, TN
• Hilton Head, SC
• Houston, TX
• Indianapolis, IN
• Jackson Hole, WY
• Kansas City, MO
• Lake Geneva, WI
• Little Rock, AR
• Louisville, KY
• Madison, WI
• Memphis, TN
• Milwaukee, WI
• Minneapolis–St. Paul, MN
• Moab & Arches, UT
• Myrtle Beach, SC
• New Orleans, LA
• Oklahoma City, OK
• Omaha, NE
• Pensacola, FL
• Pittsburgh, PA
• Portland, ME
• Providence, RI
• Raleigh-Durham, NC
• Richmond, VA
• Sacramento, CA
• San Juan, PR
• Saugatuck, MI
• Seattle, WA
• Spokane, WA
• St. Louis, MO
• Traverse City, MI
• Tulsa, OK
• Virginia Beach, VA