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: 20
Weekends covered: 8
Weekend of Sat 24 Oct
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| New Orleans | $348 | Sat 24 Oct 06:00 | Mon 26 Oct 10:37 | 1 weekday | ORD → MSY | out 1 stop, back 1 stop | Frontier Airlines | found yesterday | See prices for these dates | Check today's price |
| Dallas | $321 | Fri 23 Oct 12:26 | Mon 26 Oct 09:30 | 2 weekdays | ORD → DFW | out nonstop, back 1 stop | Frontier Airlines | found 5 days ago | See prices for these dates | Check today's price |
| Ontario | $321 | Sat 24 Oct 06:15 | Sun 25 Oct 23:55 | None | MDW → ONT | out 1 stop, back nonstop | Southwest Airlines | found 4 days ago | See prices for these dates | Check today's price |
Weekend of Sat 31 Oct
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| Fort Lauderdale | $245 | Thu 29 Oct 08:00 | Mon 2 Nov 13:05 | 3 weekdays | ORD → FLL | out nonstop, back nonstop | Frontier Airlines | found today | See prices for these dates | Check today's price |
| New York | $353 | Sat 31 Oct 07:15 | Mon 2 Nov 11:35 | 1 weekday | ORD → LGA | out 1 stop, back 1 stop | Frontier Airlines | found today | See prices for these dates | Check today's price |
| Orlando | $239 | Fri 30 Oct 08:44 | Mon 2 Nov 08:10 | 2 weekdays | RFD → SFB | out nonstop, back nonstop | Allegiant Air | found 3 days ago | See prices for these dates | Check today's price |
| Denver | $272 | Sat 31 Oct 06:30 | Sun 1 Nov 20:55 | None | ORD → DEN | out nonstop, back nonstop | Frontier Airlines | found 2 days ago | See prices for these dates | Check today's price |
| Atlanta | $220 | Fri 30 Oct 18:42 | Mon 2 Nov 22:48 | 1 weekday | MDW → ATL | out nonstop, back nonstop | Frontier Airlines | found 4 days ago | See prices for these dates | Check today's price |
| Phoenix | $276 | Fri 30 Oct 12:17 | Mon 2 Nov 07:30 | 2 weekdays | RFD → AZA | out nonstop, back nonstop | Allegiant Air | found 5 days ago | See prices for these dates | Check today's price |
| Boston | $308 | Fri 30 Oct 14:26 | Sun 1 Nov 12:39 | 1 weekday | MDW → BOS | out 1 stop, back 1 stop | Allegiant Air | found 6 days ago | See prices for these dates | Check today's price |
| Puebla | $409 | Sat 31 Oct 14:11 | Mon 2 Nov 20:50 | 1 weekday | ORD → PBC | out 1 stop, back nonstop | Frontier Airlines | found 5 days ago | See prices for these dates | Check today's price |
1 more place this weekend
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| Los Angeles | $449 | Fri 30 Oct 08:29 | Mon 2 Nov 18:37 | 2 weekdays | ORD → LAX | out nonstop, back nonstop | American Airlines | found 4 days ago | See prices for these dates | Check today's price |
Weekend of Sat 7 Nov
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| Raleigh | $374 | Thu 5 Nov 09:30 | Sun 8 Nov 21:30 | 2 weekdays | RFD → RDU | out 2 stops, back 1 stop | Allegiant Air | found yesterday | See prices for these dates | Check today's price |
| Philadelphia | $235 | Sat 7 Nov 07:05 | Mon 9 Nov 21:09 | 1 weekday | ORD → PHL | out 1 stop, back nonstop | Frontier Airlines | found 3 days ago | See prices for these dates | Check today's price |
| Las Vegas | $286 | Sat 7 Nov 12:20 | Mon 9 Nov 07:22 | 1 weekday | MDW → LAS | out 1 stop, back 1 stop | Frontier Airlines | found 3 days ago | See prices for these dates | Check today's price |
| Orlando | $432 | Thu 5 Nov 13:08 | Mon 9 Nov 08:00 | 3 weekdays | RFD → MCO | out 1 stop, back nonstop | Allegiant Air | found 3 days ago | See prices for these dates | Check today's price |
| Nashville | $493 | Fri 6 Nov 19:58 | Sun 8 Nov 10:46 | None | RFD → BNA | out 2 stops, back nonstop | Allegiant Air | found 2 days ago | See prices for these dates | Check today's price |
| Atlanta | $133 | Thu 5 Nov 19:50 | Mon 9 Nov 17:15 | 2 weekdays | ORD → ATL | out nonstop, back nonstop | Frontier Airlines | found 5 days ago | See prices for these dates | Check today's price |
| New York | $254 | Thu 5 Nov 21:48 | Sun 8 Nov 10:45 | 1 weekday | ORD → EWR | out nonstop, back nonstop | United Airlines | found 7 days ago | See prices for these dates | Check today's price |
Weekend of Sat 14 Nov
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| New York | $283 | Thu 12 Nov 19:43 | Mon 16 Nov 19:50 | 2 weekdays | ORD → EWR | out nonstop, back nonstop | American Airlines | found 2 days ago | See prices for these dates | Check today's price |
| Baltimore | $215 | Thu 12 Nov 06:00 | Sun 15 Nov 09:53 | 2 weekdays | ORD → BWI | out nonstop, back nonstop | Frontier Airlines | found 4 days ago | See prices for these dates | Check today's price |
| Washington | $283 | Thu 12 Nov 06:08 | Sun 15 Nov 21:59 | 2 weekdays | MDW → IAD | out 1 stop, back 2 stops | 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 | $402 | Fri 20 Nov 13:16 | Mon 23 Nov 08:20 | 2 weekdays | RFD → AZA | out nonstop, back nonstop | Allegiant Air | found today | See prices for these dates | Check today's price |
| Dallas | $247 | Thu 19 Nov 10:29 | Sun 22 Nov 05:15 | 2 weekdays | ORD → DFW | out nonstop, back nonstop | Frontier Airlines | found 2 days ago | See prices for these dates | Check today's price |
| Fort Lauderdale | $198 | Thu 19 Nov 07:55 | Mon 23 Nov 21:02 | 3 weekdays | ORD → FLL | out nonstop, back nonstop | Frontier Airlines | found 6 days ago | See prices for these dates | Check today's price |
| Las Vegas | $276 | Fri 20 Nov 06:40 | Sun 22 Nov 23:26 | 1 weekday | ORD → LAS | out 1 stop, back nonstop | Frontier Airlines | found 6 days ago | See prices for these dates | Check today's price |
| New Orleans | $284 | Thu 19 Nov 06:30 | Sun 22 Nov 09:18 | 2 weekdays | ORD → MSY | out 1 stop, back 1 stop | 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 | ||
|---|---|---|---|---|---|---|---|---|---|---|
| Phoenix | $411 | Fri 27 Nov 13:16 | Sun 29 Nov 15:58 | 1 weekday | RFD → AZA | out nonstop, back nonstop | Allegiant Air | found today | See prices for these dates | Check today's price |
| Baltimore | $213 | Thu 26 Nov 14:52 | Mon 30 Nov 14:29 | 3 weekdays | ORD → BWI | out nonstop, back nonstop | Frontier Airlines | found 6 days ago | See prices for these dates | Check today's price |
| Washington | $299 | Thu 26 Nov 09:09 | Mon 30 Nov 06:50 | 3 weekdays | MDW → IAD | out 1 stop, back 1 stop | Frontier Airlines | found 6 days ago | See prices for these dates | Check today's price |
| Buffalo | $328 | Thu 26 Nov 17:12 | Sun 29 Nov 21:20 | 1 weekday | ORD → BUF | out 1 stop, back 1 stop | Frontier Airlines | found 5 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 | ||
|---|---|---|---|---|---|---|---|---|---|---|
| New York | $284 | Thu 3 Dec 17:02 | Sun 6 Dec 06:00 | 1 weekday | MDW → EWR | out 1 stop, back 1 stop | Frontier Airlines | found 19 hours ago | See prices for these dates | Check today's price |
| Las Vegas | $179 | Sat 5 Dec 06:21 | Mon 7 Dec 23:15 | 1 weekday | ORD → LAS | out nonstop, back nonstop | Frontier Airlines | found 4 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 | $202 | Fri 11 Dec 15:50 | Sun 13 Dec 09:15 | 1 weekday | MDW → MCO | out 1 stop, back 1 stop | Frontier Airlines | found 5 days ago | See prices for these dates | Check today's price |
| Miami | $430 | Fri 11 Dec 13:20 | Mon 14 Dec 07:05 | 2 weekdays | MDW → MIA | out 1 stop, back 1 stop | Southwest Airlines | found 4 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