Weekend trips from Chicago under $500
For each of the coming weekends, the cheapest return we hold from Chicago to each place: out on a Thursday, Friday or Saturday and back on the Sunday or Monday, with at least a full day there.
Places with a weekend trip: 16
Weekends covered: 9
Weekend of Sat 14 Nov
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| Dallas | $286 | Sat 14 Nov 12:20 | Mon 16 Nov 08:54 | 1 weekday | MDW → DFW | out nonstop, back nonstop | Frontier Airlines | found 4 days ago | See prices for these dates | Check today's price |
Weekend of Sat 21 Nov
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| Phoenix | $317 | Fri 20 Nov 13:16 | Mon 23 Nov 08:20 | 2 weekdays | RFD → AZA | out nonstop, back nonstop | Allegiant Air | found 2 days ago | See prices for these dates | Check today's price |
| Atlanta | $277 | Sat 21 Nov 14:40 | Sun 22 Nov | None | MDW → ATL | out nonstop, back nonstop | Frontier Airlines | found 4 days ago | See prices for these dates | Check today's price |
Weekend of Sat 28 Nov
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| Orlando | $323 | Fri 27 Nov 18:04 | Sun 29 Nov 06:10 | None | RFD → SFB | out nonstop, back nonstop | Allegiant Air | found 2 days ago | See prices for these dates | Check today's price |
| New Orleans | $344 | Fri 27 Nov 05:40 | Mon 30 Nov 18:55 | 2 weekdays | ORD → MSY | out 1 stop, back 1 stop | Frontier Airlines | found 3 days ago | See prices for these dates | Check today's price |
| Miami | $449 | Thu 26 Nov 13:16 | Sun 29 Nov 22:59 | 2 weekdays | MDW → MIA | out 1 stop, back 1 stop | Frontier Airlines | found 2 days ago | See prices for these dates | Check today's price |
| Baltimore | $224 | Thu 26 Nov 14:52 | Mon 30 Nov 14:29 | 3 weekdays | ORD → BWI | out nonstop, back nonstop | Frontier Airlines | found 4 days ago | See prices for these dates | Check today's price |
| Charlotte | $329 | Thu 26 Nov 16:00 | Sun 29 Nov 22:42 | 2 weekdays | ORD → CLT | out 1 stop, back 1 stop | Frontier Airlines | found 6 days ago | See prices for these dates | Check today's price |
| Phoenix | $362 | Fri 27 Nov 12:05 | Mon 30 Nov 20:59 | 2 weekdays | ORD → PHX | out nonstop, back 1 stop | Frontier Airlines | found 4 days ago | See prices for these dates | Check today's price |
| Washington | $429 | Thu 26 Nov 07:49 | Mon 30 Nov 01:01 | 3 weekdays | ORD → IAD | out 1 stop, back nonstop | Frontier Airlines | found 4 days ago | See prices for these dates | Check today's price |
| Las Vegas | $485 | Fri 27 Nov 11:10 | Mon 30 Nov 20:00 | 2 weekdays | MDW → LAS | out nonstop, back nonstop | Southwest Airlines | found 4 days ago | See prices for these dates | Check today's price |
Weekend of Sat 5 Dec
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| Las Vegas | $184 | Sat 5 Dec 07:25 | Sun 6 Dec 23:15 | None | ORD → LAS | out 1 stop, back nonstop | Frontier Airlines | found 2 days ago | See prices for these dates | Check today's price |
| Ontario | $242 | Sat 5 Dec 06:21 | Mon 7 Dec 11:30 | 1 weekday | ORD → ONT | out 1 stop, back 1 stop | Frontier Airlines | found 3 days ago | See prices for these dates | Check today's price |
| New York | $253 | Sat 5 Dec 12:28 | Mon 7 Dec 06:00 | 1 weekday | MDW → EWR | out 1 stop, back 1 stop | Frontier Airlines | found 2 days ago | See prices for these dates | Check today's price |
| Los Angeles | $326 | Sat 5 Dec 10:40 | Mon 7 Dec 00:12 | 1 weekday | MDW → LAX | out 1 stop, back 1 stop | Frontier Airlines | found 3 days ago | See prices for these dates | Check today's price |
| Dallas | $163 | Fri 4 Dec 08:59 | Mon 7 Dec 09:45 | 2 weekdays | ORD → DFW | out nonstop, back nonstop | Frontier Airlines | found 5 days ago | See prices for these dates | Check today's price |
| Tampa | $219 | Fri 4 Dec 07:59 | Mon 7 Dec 10:26 | 2 weekdays | ORD → TPA | out nonstop, back nonstop | Allegiant Air | found 4 days ago | See prices for these dates | Check today's price |
| Miami | $282 | Sat 5 Dec 08:30 | Sun 6 Dec 20:48 | None | ORD → MIA | out 1 stop, back 1 stop | Frontier Airlines | found 6 days ago | See prices for these dates | Check today's price |
Weekend of Sat 12 Dec
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| Orlando | $176 | Fri 11 Dec 17:02 | Mon 14 Dec 11:27 | 1 weekday | MDW → MCO | out 1 stop, back nonstop | Allegiant Air | found 2 days ago | See prices for these dates | Check today's price |
| Miami | $341 | Sat 12 Dec 12:28 | Mon 14 Dec 22:33 | 1 weekday | MDW → MIA | out 1 stop, back 1 stop | United Airlines | found 2 days ago | See prices for these dates | Check today's price |
| Tampa | $216 | Thu 10 Dec 17:02 | Mon 14 Dec 08:20 | 2 weekdays | MDW → TPA | out 1 stop, back 1 stop | Frontier Airlines | found 5 days ago | See prices for these dates | Check today's price |
Weekend of Sat 19 Dec
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| Tampa | $249 | Fri 18 Dec 06:08 | Sun 20 Dec 01:01 | 1 weekday | ORD → TPA | out nonstop, back 1 stop | Frontier Airlines | found 2 days ago | See prices for these dates | Check today's price |
| Baltimore | $260 | Fri 18 Dec 13:10 | Sun 20 Dec 10:52 | 1 weekday | ORD → BWI | out nonstop, back 1 stop | Frontier Airlines | found 3 days ago | See prices for these dates | Check today's price |
| Fort Lauderdale | $238 | Thu 17 Dec 08:59 | Sun 20 Dec 14:17 | 2 weekdays | ORD → FLL | out nonstop, back nonstop | Frontier Airlines | found 6 days ago | See prices for these dates | Check today's price |
| Charlotte | $244 | Fri 18 Dec 07:35 | Mon 21 Dec 07:56 | 2 weekdays | ORD → CLT | out 1 stop, back 1 stop | Frontier Airlines | found 4 days ago | See prices for these dates | Check today's price |
| Las Vegas | $278 | Thu 17 Dec 12:27 | Sun 20 Dec 06:20 | 2 weekdays | RFD → LAS | out nonstop, back nonstop | Allegiant Air | found 4 days ago | See prices for these dates | Check today's price |
| Miami | $278 | Thu 17 Dec 06:43 | Sun 20 Dec 21:36 | 2 weekdays | MDW → MIA | out 1 stop, back 1 stop | Frontier Airlines | found 6 days ago | See prices for these dates | Check today's price |
| New York | $314 | Fri 18 Dec 06:59 | Sun 20 Dec 08:10 | 1 weekday | ORD → LGA | out nonstop, back nonstop | American Airlines | found 5 days ago | See prices for these dates | Check today's price |
Weekend of Sat 26 Dec
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| New York | $243 | Thu 24 Dec 07:00 | Mon 28 Dec 20:30 | 3 weekdays | ORD → EWR | out nonstop, back nonstop | United Airlines | found 5 days ago | See prices for these dates | Check today's price |
| Orlando | $287 | Thu 24 Dec 13:11 | Mon 28 Dec 01:56 | 3 weekdays | MDW → MCO | out 1 stop, back nonstop | Frontier Airlines | found 4 days ago | See prices for these dates | Check today's price |
Weekend of Sat 2 Jan 2027
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| Miami | $357 | Thu 31 Dec 13:25 | Mon 4 Jan 2027 13:00 | 3 weekdays | MDW → MIA | out nonstop, back 1 stop | Southwest Airlines | found 6 days ago | See prices for these dates | Check today's price |
Weekend of Sat 23 Jan 2027
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| San Francisco | $303 | Thu 21 Jan 2027 06:21 | Sun 24 Jan 2027 18:30 | 2 weekdays | ORD → SFO | out 1 stop, back 1 stop | Frontier Airlines | found 3 days ago | See prices for these dates | Check today's price |
Every trip here gives at least 24 hours at the destination and gets you home by 6 am on the Tuesday. Times are local to each airport. "Weekdays off" counts Monday to Friday days the trip takes; a flight leaving at 5 pm or later does not take that day.
1 traveler · Economy
Prices are what travelers' searches on Aviasales found in the last 7 days, in US dollars: the price the seller showed on Aviasales; bags may cost extra. Fares change, so check today's price before you book. How our prices work