The Cheapest Tourist-Friendly US City To Fly To Out Of Chicago In January
After an undoubtedly busy holiday period, why not escape from the hustle and bustle of Chicago with a spontaneous trip? Even just a quick weekend getaway is warranted before returning to the day-to-day grind. It's generally recommended to avoid flying on the worst days of the year, such as over the holidays, but you may be surprised to know you can fly to popular U.S. cities from central hub Chicago O'Hare International Airport (ORD) for under $100 this January. In fact, right now New York City is the cheapest tourist-friendly city you can visit this January if you're flying out of Chicago.
It should be noted we landed on NYC thanks in part to our distinction of the destination being "popular" and "tourist-friendly." It could be cheaper to fly to remote towns with regional carriers, but you want to live the good life, right? Luckily, after comparing flights and fares from Kayak, Skyscanner, and Google Flights, the Big Apple consistently appeared as the least expensive destination to fly to out of Chicago O'Hare. At the time of writing, round-trip tickets for the last week of January are listed as low as $58 on Google Flights. Talk about a sweet deal!
Fly to New York and Atlanta for less than $100
The first week of January is always an expensive time to fly, but prices drop significantly once the New Year's Eve traffic has passed. When it comes to flying out from one of the world's busiest airports later in January, New York boasted attractive low prices, ranging from $58 to $95. Even with affordable airfare, however, New York tends to be a not-so-affordable destination. Accommodations, restaurants, and shopping are some areas you'll want to carefully research to keep overall travel costs low.
Travelers on a stricter budget may want to consider Atlanta. The Georgia city is the second-cheapest destination you can fly to from O'Hare International Airport, according to Google flights and the other sources mentioned above. As of the end of December, flights throughout January average around the $70 mark. Atlanta offers more free and inexpensive activities that won't break the bank, and dining on a budget is possible if you follow a local's recommendations. After all, you'll want to save some of your travel funds for your second trip of 2026.