Need a last-minute escape from the Windy City? After analyzing weekend flight pricing and availability patterns from Chicago's airports, we've found the top 8 cheapest nonstop roundtrip destinations reachable on a 3-day weekend. All cities on this list are connected by direct, roundtrip flights—no connections, no wasted travel time.
Here's what we found. The top 8 cheapest weekend destinations from Chicago:
- Quincy, IL (UIN)
- Minneapolis, MN (MSP)
- Fort Worth, TX (DFW)
- Fort Lauderdale, FL (FLL)
- San Diego, CA (SAN)
- New York, NY (LGA)
- Cedar Rapids, IA (CID)
- Charleston, WV (CRW)
1) Quincy, IL (UIN) for $100
Our flights study shows that Quincy, IL (UIN) from Chicago, IL surfaced only occasionally. Pricing is essentially equal between both windows. The 7:40 pm Friday departure is the most common time we tracked.
Top things to do: Quincy, IL
Quincy is a charming riverfront town—the historic downtown and Gem City waterfront offer architectural walks and river bluffs, while the Mississippi River setting provides scenic walking. Midwestern hospitality and local character create genuine appeal.
2) Minneapolis, MN (MSP) for $150
Our flights study shows that Minneapolis, MN (MSP) from Chicago, IL appeared with moderate frequency. Thu–Sun tends to be the cheaper option. The 6:08 pm Friday departure is the most common time we tracked.
Top things to do: Minneapolis, MN
Minneapolis punches above its Midwest reputation—the Chain of Lakes system offers kayaking and scenic urban trails. The city combines vibrant neighborhoods with world-class museums and dining. Check out our Weekend Guide to Minneapolis for even more travel ideas.
3) Fort Worth, TX (DFW) for $200
Our flights study shows that Fort Worth, TX (DFW) from Chicago, IL appeared with moderate frequency. Thu–Sun tends to be the cheaper option. The 8:10 pm Friday departure is the most common time we tracked.
Top things to do: Fort Worth, TX
Fort Worth delivers authentic Texas culture—the Stockyards and Western heritage museums showcase cowboy history, while vibrant cultural districts offer dining and nightlife. Rideshares and walking work downtown; the city blends heritage with modern energy. Check out our Weekend Guide to Fort Worth for even more travel ideas.
4) Fort Lauderdale, FL (FLL) for $200
Our flights study shows that Fort Lauderdale, FL (FLL) from Chicago, IL appeared across most of our searches. Fri–Mon tends to be the cheaper option. The 6:10 pm Friday departure is the most common time we tracked.
Top things to do: Fort Lauderdale, FL
Fort Lauderdale offers beach culture and waterfront dining—Las Olas Boulevard and the beach scene deliver upscale coastal appeal, while the downtown revitalization brings galleries and restaurants. Rideshares and walking work; the beach access and water recreation create year-round appeal.
5) San Diego, CA (SAN) for $250
Our flights study shows that San Diego, CA (SAN) from Chicago, IL appeared with moderate frequency. Fri–Mon tends to be the cheaper option. The 7:59 pm Friday departure is the most common time we tracked.
Top things to do: San Diego, CA
San Diego offers year-round sunshine and coastal adventure—Balboa Park delivers museums, gardens, and walkable neighborhoods. The perfect weather, vibrant food scene, and beach access create irresistible appeal. Check out our Weekend Guide to San Diego for even more travel ideas.
6) New York, NY (LGA) for $250
Our flights study shows that New York, NY (LGA) from Chicago, IL appeared with moderate frequency. Fri–Mon tends to be the cheaper option. The 6:20 pm Friday departure is the most common time we tracked.
Top things to do: New York, NY
New York City never sleeps—world-class museums, Broadway shows, and iconic landmarks like the Statue of Liberty create unforgettable experiences. The diverse neighborhoods, exceptional food scene, and cultural institutions deliver endless discovery. Check out our Weekend Guide to New York for even more travel ideas.
7) Cedar Rapids, IA (CID) for $250
Our flights study shows that Cedar Rapids, IA (CID) from Chicago, IL surfaced only occasionally. Fri–Mon tends to be the cheaper option. The 9:35 pm Friday departure is the most common time we tracked.
Top things to do: Cedar Rapids, IA
Cedar Rapids combines cultural attractions with Midwestern charm—the Cedar Rapids Museum of Art offers exceptional collections. Riverfront trails and the vibrant downtown provide weekend exploration with genuine Midwestern character.
8) Charleston, WV (CRW) for $250
Our flights study shows that Charleston, WV (CRW) from Chicago, IL surfaced only occasionally. Thu–Sun tends to be the cheaper option. The 6:00 pm Friday departure is the most common time we tracked.
Top things to do: Charleston, WV
Charleston delivers river culture and creative revival—the New River Gorge and downtown riverside offer outdoor and cultural appeal, while galleries and restaurants showcase revitalization. Walking and rideshares work; the outdoor recreation access creates adventure potential.
Ready to escape Chicago for a weekend?
On Skyweekend, you could find cheap, last-minute weekend flights from Chicago to anywhere across the US. Our flights are roundtrip and perfectly-timed for a weekend getaway. Explore flights.
