Looking for a quick escape from Chicago? Weekend getaways are totally doable, especially if you know where to look. We focus on trips that let you fly out Friday evening and be back by Sunday, keeping your costs down and your packing light – think carry-on only!
When planning your weekend adventure, keep an eye on the total round-trip price. For example, in late October, you could fly to Dallas for as low as $134 with Frontier Airlines, or Ontario for $258. Early November offers Ontario for $143 or Dallas for $144. Mid-November brings options like Miami for $177 or Fort Lauderdale for $196. These prices are for the flight only, so factor in any extra costs like seat selection or baggage if you can't stick to a personal item.
The key to a budget-friendly weekend trip is flexibility with your destination and sticking to the essentials. We highlight the cheapest and closest options to help you maximize your two free days without breaking the bank.
FAQ
What are the cheapest weekend destinations from Chicago?
For the weekend of October 30 – November 1, 2026, Dallas is the cheapest at $134 with Frontier Airlines. For November 6 – November 8, 2026, Ontario is $143 with Frontier Airlines, and for November 13 – November 15, 2026, Miami is $177 with Frontier Airlines.
Which airlines offer the lowest fares for weekend trips from Chicago?
Frontier Airlines frequently offers the lowest fares for weekend getaways from Chicago, with options like Dallas, Ontario, Houston, Washington, and Miami appearing in the top deals.
Are there any West Coast destinations affordable for a weekend from Chicago?
Yes, for the weekend of November 6 – November 8, 2026, you could fly to Los Angeles for $175 with Frontier Airlines. For October 30 – November 1, 2026, Ontario is $258 with Frontier Airlines.