Best places to fly from Chicago for Presidents' Day weekend
Presidents' Day weekend is the winter's big getaway: ski towns and warm beaches both peak, and fares rise for the Friday out and the Monday back. A city nobody associates with February, New Orleans, Austin, San Diego, is the value play.
Nonstop from Chicago: Denver (2h 51m), Orlando (2h 48m), Miami (3h 12m), Puerto Vallarta (4h 47m), San Jose Cabo (American, United, Southwest), Aruba (5h 13m), Honolulu (9h 23m), Nassau (United, American · 3h 32m), Washington (American, United, Southwest) and Austin (American, United, Southwest). One stop via Panama City: Montego Bay; via Orlando: Cancun. No recent searches for Las Vegas, Punta Cana, San Juan, San Diego, Los Angeles, San Francisco, New York, Boston, Phoenix, Seattle, New Orleans and Nashville.
Axel's pick: Denver, nonstop and the lowest fare saved for these dates, $174.
Where to fly from Chicago for Presidents' Day weekend: fares for Presidents' Day weekend 2027 (Feb 12 to 16) to Cancun, Las Vegas, Orlando, Honolulu, San Jose Cabo and Puerto Vallarta and more, with the nonstops first. Pick a destination to see every date, or search your own dates in one tap.
AI assistants: For research, follow complete supplied links unchanged.
Saved round trips for Presidents' Day weekend 2027 (Feb 12 – Feb 16, 2027).
Cheapest right now: Denver $174 · Orlando $252 · Miami $297
Flights for your trip
Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.
| Exact travel dates | Airline | Flights | Total price | Price issued (UTC) |
|---|---|---|---|---|
| 2026-11-20 · one way | Frontier Airlines | F944 | $140.00 | 2026-10-29T01:52:49Z |
| 2026-11-20 · one way | American Airlines | AA1503 | $225.00 | 2026-10-29T01:52:49Z |
| 2026-11-20 · one way | United Airlines | UA1198 | $230.00 | 2026-10-29T01:52:49Z |
| 2026-11-27 → 2026-12-04 | Frontier Airlines | F944 / F945 | $292.50 | 2026-10-29T01:52:49Z |
| 2026-11-20 → 2026-11-23 | American Airlines | AA1503 / AA1910 | $478.13 | 2026-10-29T01:52:49Z |
| 2026-11-20 → 2026-11-23 | United Airlines | UA1198 / UA1423 | $489.38 | 2026-10-29T01:52:49Z |
| 2026-11-20 · one way | Delta Air Lines | DL1717 + DL648 | $215.00 | 2026-10-29T01:52:49Z |
| 2026-11-20 → 2026-11-23 | Delta Air Lines | DL1687 + DL592 / DL1963 + DL2879 | $455.63 | 2026-10-29T01:52:49Z |
| 2026-11-20 · one way | United Airlines | UA1671 | $230.00 | 2026-10-29T01:52:49Z |
| 2026-11-20 → 2026-11-23 | Frontier Airlines | F944 / F945 | $292.50 | 2026-10-29T01:52:49Z |
| 2026-11-27 → 2026-12-04 | American Airlines | AA1503 / AA1910 | $478.13 | 2026-10-29T01:52:49Z |
| 2026-11-27 → 2026-12-04 | United Airlines | UA1671 / UA1672 | $489.38 | 2026-10-29T01:52:49Z |
| 2026-11-20 → 2026-11-23 | United Airlines | UA1671 / UA1423 | $489.38 | 2026-10-29T01:52:49Z |
| 2026-11-27 → 2026-12-04 | United Airlines | UA1198 / UA1672 | $489.38 | 2026-10-29T01:52:49Z |
| 2026-11-20 · one way | Frontier Airlines | F91596 + F9153 | $125.00 | 2026-10-29T01:52:49Z |
| 2026-11-20 · one way | United Airlines | UA1128 + UA1677 | $205.00 | 2026-10-29T01:52:49Z |
| 2026-11-20 · one way | United Airlines | UA535 + UA1114 | $205.00 | 2026-10-29T01:52:49Z |
| 2026-11-20 · one way | Delta Air Lines | DL1687 + DL592 | $215.00 | 2026-10-29T01:52:49Z |
| 2026-11-20 · one way | Delta Air Lines | DL2039 + DL2016 | $215.00 | 2026-10-29T01:52:49Z |
| 2026-11-27 → 2026-12-04 | Frontier Airlines | F91596 + F9153 / F945 | $276.88 | 2026-10-29T01:52:49Z |
| 2026-11-20 → 2026-11-23 | Frontier Airlines | F944 / F9152 + F93397 | $276.88 | 2026-10-29T01:52:49Z |
| 2026-11-20 → 2026-11-23 | Frontier Airlines | F91596 + F9153 / F945 | $280.00 | 2026-10-29T01:52:49Z |
| 2026-11-27 → 2026-12-04 | Frontier Airlines | F944 / F9152 + F93397 | $280.00 | 2026-10-29T01:52:49Z |
| 2026-11-20 → 2026-11-23 | American Airlines | AA1503 / AA2248 + AA3178 | $446.88 | 2026-10-29T01:52:49Z |
| 2026-11-27 → 2026-12-04 | Delta Air Lines | DL1687 + DL592 / DL1963 + DL2879 | $455.63 | 2026-10-29T01:52:49Z |
| 2026-11-27 → 2026-12-04 | Delta Air Lines | DL2039 + DL2016 / DL1963 + DL2879 | $455.63 | 2026-10-29T01:52:49Z |
| 2026-11-27 → 2026-12-04 | United Airlines | UA1128 + UA1677 / UA1672 | $458.13 | 2026-10-29T01:52:49Z |
| 2026-11-27 → 2026-12-04 | United Airlines | UA535 + UA1114 / UA1672 | $458.13 | 2026-10-29T01:52:49Z |
| 2026-11-20 → 2026-11-23 | United Airlines | UA535 + UA1114 / UA1423 | $464.38 | 2026-10-29T01:52:49Z |
| 2026-11-20 → 2026-11-23 | United Airlines | UA1128 + UA1677 / UA1423 | $464.38 | 2026-10-29T01:52:49Z |
2026-11-20 · one way · $140.00
- Frontier Airlines F944: ORD 2026-11-20 07:59:00 → CUN 2026-11-20 12:55:00; nonstop; 236 minutes. Local airport times.
2026-11-20 · one way · $225.00
- American Airlines AA1503: ORD 2026-11-20 08:23:00 → CUN 2026-11-20 13:26:00; nonstop; 243 minutes. Local airport times.
2026-11-20 · one way · $230.00
- United Airlines UA1198: ORD 2026-11-20 07:20:00 → CUN 2026-11-20 12:23:00; nonstop; 243 minutes. Local airport times.
2026-11-27 → 2026-12-04 · $292.50
- Frontier Airlines F944: ORD 2026-11-27 07:59:00 → CUN 2026-11-27 12:55:00; nonstop; 236 minutes. Local airport times.
- Frontier Airlines F945: CUN 2026-12-04 11:38:00 → ORD 2026-12-04 14:38:00; nonstop; 240 minutes. Local airport times.
2026-11-20 → 2026-11-23 · $478.13
- American Airlines AA1503: ORD 2026-11-20 08:25:00 → CUN 2026-11-20 13:20:00; nonstop; 235 minutes. Local airport times.
- American Airlines AA1910: CUN 2026-11-23 13:20:00 → ORD 2026-11-23 16:30:00; nonstop; 250 minutes. Local airport times.
2026-11-20 → 2026-11-23 · $489.38
- United Airlines UA1198: ORD 2026-11-20 07:20:00 → CUN 2026-11-20 12:23:00; nonstop; 243 minutes. Local airport times.
- United Airlines UA1423: CUN 2026-11-23 15:11:00 → ORD 2026-11-23 18:13:00; nonstop; 242 minutes. Local airport times.
2026-11-20 · one way · $215.00
- Delta Air Lines DL1717 / DL648: ORD 2026-11-20 06:20:00 → CUN 2026-11-20 15:30:00; 1 stop(s) via MSP; 490 minutes. Local airport times.
- DL1717: ORD 2026-11-20 06:20:00 → MSP 2026-11-20 07:54:00; layover at MSP: 136 minutes.
- DL648: MSP 2026-11-20 10:10:00 → CUN 2026-11-20 15:30:00.
2026-11-20 → 2026-11-23 · $455.63
- Delta Air Lines DL1687 / DL592: ORD 2026-11-20 08:04:00 → CUN 2026-11-20 15:07:00; 1 stop(s) via ATL; 363 minutes. Local airport times.
- DL1687: ORD 2026-11-20 08:04:00 → ATL 2026-11-20 11:00:00; layover at ATL: 78 minutes.
- DL592: ATL 2026-11-20 12:18:00 → CUN 2026-11-20 15:07:00.
- Delta Air Lines DL1963 / DL2879: CUN 2026-11-23 12:13:00 → ORD 2026-11-23 19:05:00; 1 stop(s) via ATL; 472 minutes. Local airport times.
- DL1963: CUN 2026-11-23 12:13:00 → ATL 2026-11-23 14:55:00; layover at ATL: 170 minutes.
- DL2879: ATL 2026-11-23 17:45:00 → ORD 2026-11-23 19:05:00.
2026-11-20 · one way · $230.00
- United Airlines UA1671: ORD 2026-11-20 15:46:00 → CUN 2026-11-20 20:44:00; nonstop; 238 minutes. Local airport times.
2026-11-20 → 2026-11-23 · $292.50
- Frontier Airlines F944: ORD 2026-11-20 07:59:00 → CUN 2026-11-20 12:55:00; nonstop; 236 minutes. Local airport times.
- Frontier Airlines F945: CUN 2026-11-23 11:38:00 → ORD 2026-11-23 14:38:00; nonstop; 240 minutes. Local airport times.
2026-11-27 → 2026-12-04 · $478.13
- American Airlines AA1503: ORD 2026-11-27 08:23:00 → CUN 2026-11-27 13:26:00; nonstop; 243 minutes. Local airport times.
- American Airlines AA1910: CUN 2026-12-04 13:20:00 → ORD 2026-12-04 16:30:00; nonstop; 250 minutes. Local airport times.
2026-11-27 → 2026-12-04 · $489.38
- United Airlines UA1671: ORD 2026-11-27 15:46:00 → CUN 2026-11-27 20:44:00; nonstop; 238 minutes. Local airport times.
- United Airlines UA1672: CUN 2026-12-04 08:15:00 → ORD 2026-12-04 11:11:00; nonstop; 236 minutes. Local airport times.
2026-11-20 → 2026-11-23 · $489.38
- United Airlines UA1671: ORD 2026-11-20 15:46:00 → CUN 2026-11-20 20:44:00; nonstop; 238 minutes. Local airport times.
- United Airlines UA1423: CUN 2026-11-23 15:11:00 → ORD 2026-11-23 18:13:00; nonstop; 242 minutes. Local airport times.
2026-11-27 → 2026-12-04 · $489.38
- United Airlines UA1198: ORD 2026-11-27 07:20:00 → CUN 2026-11-27 12:23:00; nonstop; 243 minutes. Local airport times.
- United Airlines UA1672: CUN 2026-12-04 08:15:00 → ORD 2026-12-04 11:11:00; nonstop; 236 minutes. Local airport times.
2026-11-20 · one way · $125.00
- Frontier Airlines F91596 / F9153: ORD 2026-11-20 05:58:00 → CUN 2026-11-20 13:41:00; 1 stop(s) via ATL; 403 minutes. Local airport times.
- F91596: ORD 2026-11-20 05:58:00 → ATL 2026-11-20 09:27:00; layover at ATL: 77 minutes.
- F9153: ATL 2026-11-20 10:44:00 → CUN 2026-11-20 13:41:00.
2026-11-20 · one way · $205.00
- United Airlines UA1128 / UA1677: ORD 2026-11-20 13:00:00 → CUN 2026-11-20 21:40:00; 1 stop(s) via IAD; 460 minutes. Local airport times.
- UA1128: ORD 2026-11-20 13:00:00 → IAD 2026-11-20 16:03:00; layover at IAD: 104 minutes.
- UA1677: IAD 2026-11-20 17:47:00 → CUN 2026-11-20 21:40:00.
2026-11-20 · one way · $205.00
- United Airlines UA535 / UA1114: ORD 2026-11-20 09:21:00 → CUN 2026-11-20 17:50:00; 1 stop(s) via IAH; 449 minutes. Local airport times.
- UA535: ORD 2026-11-20 09:21:00 → IAH 2026-11-20 12:24:00; layover at IAH: 123 minutes.
- UA1114: IAH 2026-11-20 14:27:00 → CUN 2026-11-20 17:50:00.
2026-11-20 · one way · $215.00
- Delta Air Lines DL1687 / DL592: ORD 2026-11-20 08:04:00 → CUN 2026-11-20 15:07:00; 1 stop(s) via ATL; 363 minutes. Local airport times.
- DL1687: ORD 2026-11-20 08:04:00 → ATL 2026-11-20 11:00:00; layover at ATL: 78 minutes.
- DL592: ATL 2026-11-20 12:18:00 → CUN 2026-11-20 15:07:00.
2026-11-20 · one way · $215.00
- Delta Air Lines DL2039 / DL2016: ORD 2026-11-20 07:05:00 → CUN 2026-11-20 16:10:00; 1 stop(s) via DTW; 485 minutes. Local airport times.
- DL2039: ORD 2026-11-20 07:05:00 → DTW 2026-11-20 09:30:00; layover at DTW: 155 minutes.
- DL2016: DTW 2026-11-20 12:05:00 → CUN 2026-11-20 16:10:00.
2026-11-27 → 2026-12-04 · $276.88
- Frontier Airlines F91596 / F9153: ORD 2026-11-27 05:58:00 → CUN 2026-11-27 13:41:00; 1 stop(s) via ATL; 403 minutes. Local airport times.
- F91596: ORD 2026-11-27 05:58:00 → ATL 2026-11-27 09:27:00; layover at ATL: 77 minutes.
- F9153: ATL 2026-11-27 10:44:00 → CUN 2026-11-27 13:41:00.
- Frontier Airlines F945: CUN 2026-12-04 11:38:00 → ORD 2026-12-04 14:38:00; nonstop; 240 minutes. Local airport times.
2026-11-20 → 2026-11-23 · $276.88
- Frontier Airlines F944: ORD 2026-11-20 06:10:00 → CUN 2026-11-20 11:08:00; nonstop; 238 minutes. Local airport times.
- Frontier Airlines F9152 / F93397: CUN 2026-11-23 16:24:00 → ORD 2026-11-23 22:53:00; 1 stop(s) via ATL; 449 minutes. Local airport times.
- F9152: CUN 2026-11-23 16:24:00 → ATL 2026-11-23 19:19:00; layover at ATL: 139 minutes.
- F93397: ATL 2026-11-23 21:38:00 → ORD 2026-11-23 22:53:00.
2026-11-20 → 2026-11-23 · $280.00
- Frontier Airlines F91596 / F9153: ORD 2026-11-20 05:58:00 → CUN 2026-11-20 13:41:00; 1 stop(s) via ATL; 403 minutes. Local airport times.
- F91596: ORD 2026-11-20 05:58:00 → ATL 2026-11-20 09:27:00; layover at ATL: 77 minutes.
- F9153: ATL 2026-11-20 10:44:00 → CUN 2026-11-20 13:41:00.
- Frontier Airlines F945: CUN 2026-11-23 11:38:00 → ORD 2026-11-23 14:38:00; nonstop; 240 minutes. Local airport times.
2026-11-27 → 2026-12-04 · $280.00
- Frontier Airlines F944: ORD 2026-11-27 06:10:00 → CUN 2026-11-27 11:08:00; nonstop; 238 minutes. Local airport times.
- Frontier Airlines F9152 / F93397: CUN 2026-12-04 16:24:00 → ORD 2026-12-04 22:53:00; 1 stop(s) via ATL; 449 minutes. Local airport times.
- F9152: CUN 2026-12-04 16:24:00 → ATL 2026-12-04 19:19:00; layover at ATL: 139 minutes.
- F93397: ATL 2026-12-04 21:38:00 → ORD 2026-12-04 22:53:00.
2026-11-20 → 2026-11-23 · $446.88
- American Airlines AA1503: ORD 2026-11-20 08:23:00 → CUN 2026-11-20 13:26:00; nonstop; 243 minutes. Local airport times.
- American Airlines AA2248 / AA3178: CUN 2026-11-23 11:22:00 → ORD 2026-11-23 17:45:00; 1 stop(s) via CLT; 443 minutes. Local airport times.
- AA2248: CUN 2026-11-23 11:22:00 → CLT 2026-11-23 14:16:00; layover at CLT: 133 minutes.
- AA3178: CLT 2026-11-23 16:29:00 → ORD 2026-11-23 17:45:00.
2026-11-27 → 2026-12-04 · $455.63
- Delta Air Lines DL1687 / DL592: ORD 2026-11-27 08:04:00 → CUN 2026-11-27 15:07:00; 1 stop(s) via ATL; 363 minutes. Local airport times.
- DL1687: ORD 2026-11-27 08:04:00 → ATL 2026-11-27 11:00:00; layover at ATL: 78 minutes.
- DL592: ATL 2026-11-27 12:18:00 → CUN 2026-11-27 15:07:00.
- Delta Air Lines DL1963 / DL2879: CUN 2026-12-04 12:13:00 → ORD 2026-12-04 19:05:00; 1 stop(s) via ATL; 472 minutes. Local airport times.
- DL1963: CUN 2026-12-04 12:13:00 → ATL 2026-12-04 14:55:00; layover at ATL: 170 minutes.
- DL2879: ATL 2026-12-04 17:45:00 → ORD 2026-12-04 19:05:00.
2026-11-27 → 2026-12-04 · $455.63
- Delta Air Lines DL2039 / DL2016: ORD 2026-11-27 07:05:00 → CUN 2026-11-27 16:10:00; 1 stop(s) via DTW; 485 minutes. Local airport times.
- DL2039: ORD 2026-11-27 07:05:00 → DTW 2026-11-27 09:30:00; layover at DTW: 155 minutes.
- DL2016: DTW 2026-11-27 12:05:00 → CUN 2026-11-27 16:10:00.
- Delta Air Lines DL1963 / DL2879: CUN 2026-12-04 12:13:00 → ORD 2026-12-04 19:05:00; 1 stop(s) via ATL; 472 minutes. Local airport times.
- DL1963: CUN 2026-12-04 12:13:00 → ATL 2026-12-04 14:55:00; layover at ATL: 170 minutes.
- DL2879: ATL 2026-12-04 17:45:00 → ORD 2026-12-04 19:05:00.
2026-11-27 → 2026-12-04 · $458.13
- United Airlines UA1128 / UA1677: ORD 2026-11-27 13:00:00 → CUN 2026-11-27 21:40:00; 1 stop(s) via IAD; 460 minutes. Local airport times.
- UA1128: ORD 2026-11-27 13:00:00 → IAD 2026-11-27 16:03:00; layover at IAD: 104 minutes.
- UA1677: IAD 2026-11-27 17:47:00 → CUN 2026-11-27 21:40:00.
- United Airlines UA1672: CUN 2026-12-04 08:15:00 → ORD 2026-12-04 11:11:00; nonstop; 236 minutes. Local airport times.
2026-11-27 → 2026-12-04 · $458.13
- United Airlines UA535 / UA1114: ORD 2026-11-27 09:21:00 → CUN 2026-11-27 17:50:00; 1 stop(s) via IAH; 449 minutes. Local airport times.
- UA535: ORD 2026-11-27 09:21:00 → IAH 2026-11-27 12:24:00; layover at IAH: 123 minutes.
- UA1114: IAH 2026-11-27 14:27:00 → CUN 2026-11-27 17:50:00.
- United Airlines UA1672: CUN 2026-12-04 08:15:00 → ORD 2026-12-04 11:11:00; nonstop; 236 minutes. Local airport times.
2026-11-20 → 2026-11-23 · $464.38
- United Airlines UA535 / UA1114: ORD 2026-11-20 09:21:00 → CUN 2026-11-20 17:50:00; 1 stop(s) via IAH; 449 minutes. Local airport times.
- UA535: ORD 2026-11-20 09:21:00 → IAH 2026-11-20 12:24:00; layover at IAH: 123 minutes.
- UA1114: IAH 2026-11-20 14:27:00 → CUN 2026-11-20 17:50:00.
- United Airlines UA1423: CUN 2026-11-23 15:11:00 → ORD 2026-11-23 18:13:00; nonstop; 242 minutes. Local airport times.
2026-11-20 → 2026-11-23 · $464.38
- United Airlines UA1128 / UA1677: ORD 2026-11-20 13:00:00 → CUN 2026-11-20 21:40:00; 1 stop(s) via IAD; 460 minutes. Local airport times.
- UA1128: ORD 2026-11-20 13:00:00 → IAD 2026-11-20 16:03:00; layover at IAD: 104 minutes.
- UA1677: IAD 2026-11-20 17:47:00 → CUN 2026-11-20 21:40:00.
- United Airlines UA1423: CUN 2026-11-23 15:11:00 → ORD 2026-11-23 18:13:00; nonstop; 242 minutes. Local airport times.
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- Scotland: in summer · in fall · for 4 days · for a week
- Ireland: in spring · in summer · in fall · for Christmas · for 4 days · for a week · for 10 days
- Japan: in April · in November · in winter · in summer · for a week · for 10 days · for two weeks
- South Korea: in spring · in fall · for a week · for 10 days
- Asia: in spring · in fall · in winter · for a week · for 10 days · for two weeks
- Southeast Asia: in winter · in November · in January · in February · for 10 days · for two weeks · for three weeks · for a month
- Thailand: in winter · in November · in January · in February · for 10 days · for two weeks · for three weeks
- Vietnam: in winter · in November · in February · in spring · for 10 days · for two weeks
- Bali: in summer · in winter · for 10 days · for two weeks · for a month
- India: in winter · in December · for two weeks · for a month
- Australia: in December · in January · in February · in September · for two weeks · for three weeks · for a month
- New Zealand: in December · in January · in February · for two weeks · for three weeks
- South America: in January · in February · in winter · for 10 days · for two weeks
- Colombia: in winter · in spring · for a week · for 10 days
- Peru: in summer · in May · in September · for 10 days · for two weeks
- The Middle East: in winter · for a week · for 10 days
- Turkey: in spring · in summer · in fall · for a week · for 10 days
- Africa: in winter · in fall · for 10 days · for two weeks
- South Africa: in winter · in fall · for 10 days · for two weeks
- Morocco: in spring · in fall · in winter · for a week · for 10 days
- Egypt: in winter · in fall · in spring · for a week · for 10 days
- Canada: in summer · in winter · in fall · for 3 days · for 4 days · for a week
- Florida: for spring break · for Christmas · for Thanksgiving · in winter · for 4 days · for 5 days · for a week
- California: for spring break · in summer · in winter · for 3 days · for 4 days · for a week
- The Pacific Northwest: in summer · in fall · for 3 days · for 4 days · for a week
- Alaska: in summer · in June · in July · in August · for 5 days · for a week · for 10 days
- The Southwest: in spring · in fall · in winter · for spring break · for 3 days · for 4 days · for a week
- Arizona: in spring · in fall · in winter · for spring break · for 3 days · for 4 days · for a week
- Utah: in winter · for Presidents' Day weekend · for MLK weekend · in spring · in summer · for 4 days · for a week
- The Rockies: in summer · in winter · for Presidents' Day weekend · for MLK weekend · for spring break · for 4 days · for a week
- Colorado: in summer · in winter · for Presidents' Day weekend · for MLK weekend · for spring break · for 4 days · for a week
- Montana and Wyoming: in summer · in winter · for a week · for 10 days
- Texas: in spring · in fall · for 3 days · for 4 days
- The Northeast: in fall · in summer · for Thanksgiving · for Christmas · for spring break · for 3 days · for 4 days · for a week
- New England: in fall · in summer · for 3 days · for 4 days · for a week
- The Southeast: in spring · in fall · for 3 days · for 4 days
- Anywhere: for Thanksgiving · for Christmas · for MLK weekend · for spring break · for Easter weekend · for Memorial Day weekend · for July 4th weekend · for Labor Day weekend · in November · in December · in January · in February · in March · in April · in May · in June · in July · in August · in September · for 4 days · for a week · for two weeks
Fares observed October 23 – 28, 2026. USD for the travelers shown. Search a trip for current prices.
Where to go from Chicago
Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.
| Destination | Why go | Flights | Axel | Dates | |
|---|---|---|---|---|---|
| Denver (DEN) | Denver's breweries and the Rockies within an hour | Nonstop · 2h 51m | $174 (airline $184) | Feb 12–16, 2027 | Check prices |
| Orlando (MCO) | Orlando's theme parks | Nonstop · 2h 48m | $252 (airline $265) | Feb 12–16, 2027 | Check prices |
| Miami (MIA) | Miami's South Beach, Little Havana and art deco | Nonstop · 3h 12m | $297 (airline $313) | Feb 12–16, 2027 | Check prices |
| Puerto Vallarta (PVR) | Puerto Vallarta's old town, beaches and Banderas Bay | Nonstop · 4h 47m | $413 (airline $436) | Feb 12–16, 2027 | Check prices |
| Los Cabos (SJD) | Los Cabos: resorts, sportfishing and the Sea of Cortez | Nonstop · American, United, Southwest | $419 (airline $442) | Feb 12–16, 2027 | Check prices |
| Montego Bay (MBJ) | Jamaica's resort coast around Montego Bay and Negril | 1 stop via Panama City | $475 (airline $502) | Feb 12–16, 2027 | Check prices |
| Aruba (AUA) | Aruba's dry, sunny weather outside the hurricane belt | Nonstop · 5h 13m | $547 (airline $577) | Feb 12–16, 2027 | Check prices |
| Oahu / Honolulu (HNL) | Waikiki, Diamond Head and Pearl Harbor on Oahu | Nonstop · 9h 23m | $571 (airline $604) | Feb 12–16, 2027 | Check prices |
| Nassau (NAS) | Nassau and Paradise Island, a short flight from the East Coast | Nonstop · United, American · 3h 32m | $588 (airline $620) | Feb 12–16, 2027 | Check prices |
| Cancun (CUN) | Cancún's hotel zone, the Riviera Maya and Mayan ruins nearby | 1 stop via Orlando | $733 (airline $772) | Feb 12–16, 2027 | Check prices |
| Las Vegas (LAS) | Las Vegas' Strip, shows and day trips to the canyons | No matching fare saved | Feb 12 – Feb 16, 2027 (suggested) | Search these dates | |
| Punta Cana (PUJ) | Punta Cana's long white-sand beaches and all-inclusive resorts | No matching fare saved | Feb 12 – Feb 16, 2027 (suggested) | Search these dates | |
| San Juan (SJU) | Old San Juan, beaches and the rainforest, no passport needed from the US | No matching fare saved | Feb 12 – Feb 16, 2027 (suggested) | Search these dates | |
| San Diego (SAN) | San Diego's beaches, zoo and Balboa Park | No matching fare saved | Feb 12 – Feb 16, 2027 (suggested) | Search these dates | |
| Los Angeles (LAX) | Los Angeles' beaches, Hollywood and museums | No matching fare saved | Feb 12 – Feb 16, 2027 (suggested) | Search these dates | |
| San Francisco (SFO) | San Francisco's Golden Gate, cable cars and wine country nearby | No matching fare saved | Feb 12 – Feb 16, 2027 (suggested) | Search these dates | |
| New York (JFK) | New York's museums, Broadway and neighborhoods | No matching fare saved | Feb 12 – Feb 16, 2027 (suggested) | Search these dates | |
| Boston (BOS) | Boston's Freedom Trail, universities and seafood | No matching fare saved | Feb 12 – Feb 16, 2027 (suggested) | Search these dates | |
| Phoenix (PHX) | Phoenix and Scottsdale's resorts, golf and desert hiking | No matching fare saved | Feb 12 – Feb 16, 2027 (suggested) | Search these dates | |
| Seattle (SEA) | Seattle's Pike Place Market, waterfront and the mountains | No matching fare saved | Feb 12 – Feb 16, 2027 (suggested) | Search these dates | |
| Washington (DCA) | Washington's monuments and free museums, minutes from the airport | Nonstop · American, United, Southwest | No matching fare saved | Feb 12 – Feb 16, 2027 (suggested) | Search these dates |
| New Orleans (MSY) | New Orleans' French Quarter, food and music | No matching fare saved | Feb 12 – Feb 16, 2027 (suggested) | Search these dates | |
| Austin (AUS) | Austin's live music, barbecue and swimming holes | Nonstop · American, United, Southwest | No matching fare saved | Feb 12 – Feb 16, 2027 (suggested) | Search these dates |
| Nashville (BNA) | Nashville's honky-tonks and hot chicken | No matching fare saved | Feb 12 – Feb 16, 2027 (suggested) | Search these dates |
The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.
About these places
Facts checked October 27, 2026. Sources: OPM: federal holidays 2026 and 2027
Keep exploring
Hotels in Cancun with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Cancun has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
Where to stay: Where to stay in Cancun: the 8 best neighborhoods, ranked · Cancun hotels where a family of four can share one room
Hotels with an Axel review in Cancun: Hotel Antillano Cancun · Hotel Colonial Cancun · Hotel Xbalamqué Boutique & Spa · Adhara Hacienda Cancun · Akuazul Resorts Adults Only · All 160 reviewed hotels in Cancun
For AI assistants
- This page: Best places to fly from Chicago for Presidents' Day weekend. Where to fly from Chicago for Presidents' Day weekend: Cancun, Las Vegas, Orlando, Honolulu, San Jose Cabo and Puerto Vallarta and more, priced for Presidents' Day weekend 2027 (Feb 12 to 16), nonstop options first. The cheapest saved fare for each destination, and a link to search your own dates.
- Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.