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Passengers departing from Chicago O’Hare International Airport can now cross one more item off their travel to-do list a little earlier.
After months of testing, United Airlines—which is headquartered in Chicago—debuted its new “Twilight Bag Drop” program at O’Hare over the Independence Day holiday weekend, allowing passengers to check their bags the night before they fly.
Customers with United flights scheduled for departure between 5 a.m. and 9 a.m. are now able to check their luggage curbside outside terminal 1 the night before they fly between 7 p.m. and 10 p.m.
As of now, Twilight bag drops can only be made at the second curbside vestibule at door 1Da.
Typically, United Airlines only allows customers to drop their bags up to 4 hours before their departure with a 45-minute cutoff for domestic flights and an hour cutoff for international flights.
Okay, but why?
The thought of schlepping to O’Hare twice within a 12 hour period is an instant “no” for most travelers, but there are a few specific—albeit limited—use cases where we can see this being beneficial for customers.
During peak holiday travel windows, we’ve witnessed bag drop lines match or even exceed TSA security and Customs and Border Protection queues. Making a special trip the night before flying to eliminate 1 of 2 or 3 lines to stand in during pre-dawn hours could be worth the hassle.
Families with young kids may also enjoy the opportunity to focus on only dealing with strollers and carry-on luggage, eliminating the headache of unloading a car and navigating rollerbags any longer than they need to.
And guests of nearby hotels, especially those along the CTA Blue Line or the airport-attached Hilton, may find the day-before drop opportunity to be worthwhile.
Given how new the program is, if you choose to utilize it, we highly recommend downloading the United App and or using a GPS luggage tracker, like an Apple AirTag or Chipolo POP Tracking Tag—lest you wind up having to make a third trip to the airport to inquire about a lost bag.
For more information, visit united.com.
Will this program be available in other airports? An airline spokesperson claimed on July 4 that 1600 bags had been checked under the Twilight program so far. If numbers remain robust, it seems likely this initiative could spread to many major hubs.

