Flights from San Juan to the Midwest in summer
Summer is the Midwest's season: Chicago's lakefront and festivals, Minneapolis's lakes, Milwaukee's beer gardens, all warm and bright from June to September. Fares peak in July and August.
Nonstop from San Juan: Chicago (American, United, Frontier), Chicago (Southwest), Minneapolis (Delta, Sun Country), Detroit (Delta), Saint Louis (Southwest), Kansas City (Southwest) and Columbus (Southwest). One stop via Houston: Cleveland and Cincinnati. No nonstop seen to Indianapolis, Milwaukee and Pittsburgh on the dates searched recently.
Axel's pick: Columbus, nonstop on Southwest and the lowest fare saved for these dates, $413.
Where to fly from San Juan to the Midwest in summer: saved round trips within June, July and August to Chicago, Minneapolis, Detroit, Saint Louis, Kansas City and Cleveland and more. 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 5–14 nights, entirely within Jun, Jul, Aug.
Cheapest right now: Cleveland $411 · Columbus $413 · Cincinnati $662
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 | F94789 | $130.00 | 2026-10-29T01:23:44Z |
| 2026-11-20 · one way | American Airlines | AA2279 | $215.00 | 2026-10-29T01:23:44Z |
| 2026-11-20 · one way | United Airlines | UA2089 | $220.00 | 2026-10-29T01:23:44Z |
| 2026-11-27 → 2026-12-04 | Frontier Airlines | F94789 / F93346 | $281.25 | 2026-10-29T01:23:44Z |
| 2026-11-20 → 2026-11-23 | American Airlines | AA2279 / AA2571 | $461.25 | 2026-10-29T01:23:44Z |
| 2026-11-20 → 2026-11-23 | United Airlines | UA2088 / UA695 | $472.50 | 2026-10-29T01:23:44Z |
| 2026-11-20 · one way | DM | DM1003 + DM5420 | $165.00 | 2026-10-29T01:23:44Z |
| 2026-11-20 · one way | Delta Air Lines | DL1780 + DL2804 | $210.00 | 2026-10-29T01:23:44Z |
| 2026-11-20 → 2026-11-23 | DM | DM1003 + DM5420 / DM5481 + DM1002 | $360.00 | 2026-10-29T01:23:44Z |
| 2026-11-20 · one way | American Airlines | AA2436 | $215.00 | 2026-10-29T01:23:44Z |
| 2026-11-20 · one way | United Airlines | UA2088 | $220.00 | 2026-10-29T01:23:44Z |
| 2026-11-20 → 2026-11-23 | American Airlines | AA2436 / AA2571 | $461.25 | 2026-10-29T01:23:44Z |
| 2026-11-27 → 2026-12-04 | American Airlines | AA2279 / AA2571 | $461.25 | 2026-10-29T01:23:44Z |
| 2026-11-27 → 2026-12-04 | American Airlines | AA2436 / AA2571 | $461.25 | 2026-10-29T01:23:44Z |
| 2026-11-27 → 2026-12-04 | United Airlines | UA2088 / UA1996 | $472.50 | 2026-10-29T01:23:44Z |
| 2026-11-27 → 2026-12-04 | United Airlines | UA2089 / UA1996 | $472.50 | 2026-10-29T01:23:44Z |
| 2026-11-20 → 2026-11-23 | United Airlines | UA2089 / UA695 | $472.50 | 2026-10-29T01:23:44Z |
| 2026-11-20 · one way | Frontier Airlines | F91015 + F92113 | $120.00 | 2026-10-29T01:23:44Z |
| 2026-11-20 · one way | Frontier Airlines | F92871 + F91441 | $120.00 | 2026-10-29T01:23:44Z |
| 2026-11-20 · one way | American Airlines | AA508 + AA595 | $195.00 | 2026-10-29T01:23:44Z |
| 2026-11-20 · one way | United Airlines | UA2022 + UA2331 | $200.00 | 2026-10-29T01:23:44Z |
| 2026-11-20 → 2026-11-23 | Frontier Airlines | F91015 + F92113 / F92112 + F91726 | $258.75 | 2026-10-29T01:23:44Z |
| 2026-11-20 → 2026-11-23 | Frontier Airlines | F92871 + F91441 / F92112 + F91726 | $258.75 | 2026-10-29T01:23:44Z |
| 2026-11-27 → 2026-12-04 | Frontier Airlines | F92871 + F91441 / F93346 | $268.75 | 2026-10-29T01:23:44Z |
| 2026-11-20 → 2026-11-23 | Frontier Airlines | F94789 / F92112 + F91726 | $268.75 | 2026-10-29T01:23:44Z |
| 2026-11-27 → 2026-12-04 | Frontier Airlines | F91015 + F92113 / F93346 | $268.75 | 2026-10-29T01:23:44Z |
| 2026-11-27 → 2026-12-04 | DM | DM1003 + DM5420 / DM5481 + DM1002 | $360.00 | 2026-10-29T01:23:44Z |
| 2026-11-27 → 2026-12-04 | American Airlines | AA508 + AA595 / AA2571 | $439.38 | 2026-10-29T01:23:44Z |
| 2026-11-20 → 2026-11-23 | American Airlines | AA508 + AA595 / AA2571 | $443.75 | 2026-10-29T01:23:44Z |
| 2026-11-27 → 2026-12-04 | United Airlines | UA2022 + UA2331 / UA1996 | $450.63 | 2026-10-29T01:23:44Z |
| 2026-11-27 → 2026-12-04 | United Airlines | UA2089 / UA1128 + UA2025 | $455.00 | 2026-10-29T01:23:44Z |
| 2026-11-20 → 2026-11-23 | United Airlines | UA2022 + UA2331 / UA695 | $455.00 | 2026-10-29T01:23:44Z |
2026-11-20 · one way · $130.00
- Frontier Airlines F94789: SJU 2026-11-20 22:26:00 → ORD 2026-11-21 01:33:00; nonstop; 307 minutes. Local airport times.
2026-11-20 · one way · $215.00
- American Airlines AA2279: SJU 2026-11-20 15:52:00 → ORD 2026-11-20 19:30:00; nonstop; 338 minutes. Local airport times.
2026-11-20 · one way · $220.00
- United Airlines UA2089: SJU 2026-11-20 08:25:00 → ORD 2026-11-20 11:47:00; nonstop; 322 minutes. Local airport times.
2026-11-27 → 2026-12-04 · $281.25
- Frontier Airlines F94789: SJU 2026-11-27 22:26:00 → ORD 2026-11-28 01:33:00; nonstop; 307 minutes. Local airport times.
- Frontier Airlines F93346: ORD 2026-12-04 23:53:00 → SJU 2026-12-05 06:32:00; nonstop; 279 minutes. Local airport times.
2026-11-20 → 2026-11-23 · $461.25
- American Airlines AA2279: SJU 2026-11-20 15:52:00 → ORD 2026-11-20 19:30:00; nonstop; 338 minutes. Local airport times.
- American Airlines AA2571: ORD 2026-11-23 23:00:00 → SJU 2026-11-24 05:36:00; nonstop; 276 minutes. Local airport times.
2026-11-20 → 2026-11-23 · $472.50
- United Airlines UA2088: SJU 2026-11-20 16:55:00 → ORD 2026-11-20 20:26:00; nonstop; 331 minutes. Local airport times.
- United Airlines UA695: ORD 2026-11-23 14:16:00 → SJU 2026-11-23 21:00:00; nonstop; 284 minutes. Local airport times.
2026-11-20 · one way · $165.00
- DM DM1003 / DM5420: SJU 2026-11-20 16:24:00 → ORD 2026-11-20 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
- DM1003: SJU 2026-11-20 16:24:00 → PUJ 2026-11-20 17:25:00; layover at PUJ: 105 minutes.
- DM5420: PUJ 2026-11-20 19:10:00 → ORD 2026-11-20 22:20:00.
2026-11-20 · one way · $210.00
- Delta Air Lines DL1780 / DL2804: SJU 2026-11-20 14:55:00 → ORD 2026-11-20 22:36:00; 1 stop(s) via BOS; 581 minutes. Local airport times.
- DL1780: SJU 2026-11-20 14:55:00 → BOS 2026-11-20 18:11:00; layover at BOS: 149 minutes.
- DL2804: BOS 2026-11-20 20:40:00 → ORD 2026-11-20 22:36:00.
2026-11-20 → 2026-11-23 · $360.00
- DM DM1003 / DM5420: SJU 2026-11-20 16:24:00 → ORD 2026-11-20 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
- DM1003: SJU 2026-11-20 16:24:00 → PUJ 2026-11-20 17:25:00; layover at PUJ: 105 minutes.
- DM5420: PUJ 2026-11-20 19:10:00 → ORD 2026-11-20 22:20:00.
- DM DM5481 / DM1002: ORD 2026-11-23 05:45:00 → SJU 2026-11-23 15:03:00; 1 stop(s) via PUJ; 438 minutes. Local airport times.
- DM5481: ORD 2026-11-23 05:45:00 → PUJ 2026-11-23 12:30:00; layover at PUJ: 88 minutes.
- DM1002: PUJ 2026-11-23 13:58:00 → SJU 2026-11-23 15:03:00.
2026-11-20 · one way · $215.00
- American Airlines AA2436: SJU 2026-11-20 05:00:00 → ORD 2026-11-20 08:39:00; nonstop; 339 minutes. Local airport times.
2026-11-20 · one way · $220.00
- United Airlines UA2088: SJU 2026-11-20 16:55:00 → ORD 2026-11-20 20:26:00; nonstop; 331 minutes. Local airport times.
2026-11-20 → 2026-11-23 · $461.25
- American Airlines AA2436: SJU 2026-11-20 05:00:00 → ORD 2026-11-20 08:39:00; nonstop; 339 minutes. Local airport times.
- American Airlines AA2571: ORD 2026-11-23 23:00:00 → SJU 2026-11-24 05:36:00; nonstop; 276 minutes. Local airport times.
2026-11-27 → 2026-12-04 · $461.25
- American Airlines AA2279: SJU 2026-11-27 15:52:00 → ORD 2026-11-27 19:30:00; nonstop; 338 minutes. Local airport times.
- American Airlines AA2571: ORD 2026-12-04 23:00:00 → SJU 2026-12-05 05:36:00; nonstop; 276 minutes. Local airport times.
2026-11-27 → 2026-12-04 · $461.25
- American Airlines AA2436: SJU 2026-11-27 05:00:00 → ORD 2026-11-27 08:39:00; nonstop; 339 minutes. Local airport times.
- American Airlines AA2571: ORD 2026-12-04 23:00:00 → SJU 2026-12-05 05:36:00; nonstop; 276 minutes. Local airport times.
2026-11-27 → 2026-12-04 · $472.50
- United Airlines UA2088: SJU 2026-11-27 16:55:00 → ORD 2026-11-27 20:26:00; nonstop; 331 minutes. Local airport times.
- United Airlines UA1996: ORD 2026-12-04 08:52:00 → SJU 2026-12-04 15:40:00; nonstop; 288 minutes. Local airport times.
2026-11-27 → 2026-12-04 · $472.50
- United Airlines UA2089: SJU 2026-11-27 08:25:00 → ORD 2026-11-27 11:47:00; nonstop; 322 minutes. Local airport times.
- United Airlines UA1996: ORD 2026-12-04 08:52:00 → SJU 2026-12-04 15:40:00; nonstop; 288 minutes. Local airport times.
2026-11-20 → 2026-11-23 · $472.50
- United Airlines UA2089: SJU 2026-11-20 08:25:00 → ORD 2026-11-20 11:47:00; nonstop; 322 minutes. Local airport times.
- United Airlines UA695: ORD 2026-11-23 14:16:00 → SJU 2026-11-23 21:00:00; nonstop; 284 minutes. Local airport times.
2026-11-20 · one way · $120.00
- Frontier Airlines F91015 / F92113: SJU 2026-11-20 07:28:00 → ORD 2026-11-20 14:12:00; 1 stop(s) via PHL; 524 minutes. Local airport times.
- F91015: SJU 2026-11-20 07:28:00 → PHL 2026-11-20 10:36:00; layover at PHL: 123 minutes.
- F92113: PHL 2026-11-20 12:39:00 → ORD 2026-11-20 14:12:00.
2026-11-20 · one way · $120.00
- Frontier Airlines F92871 / F91441: SJU 2026-11-20 05:19:00 → ORD 2026-11-20 12:00:00; 1 stop(s) via ATL; 521 minutes. Local airport times.
- F92871: SJU 2026-11-20 05:19:00 → ATL 2026-11-20 08:26:00; layover at ATL: 131 minutes.
- F91441: ATL 2026-11-20 10:37:00 → ORD 2026-11-20 12:00:00.
2026-11-20 · one way · $195.00
- American Airlines AA508 / AA595: SJU 2026-11-20 08:30:00 → ORD 2026-11-20 15:34:00; 1 stop(s) via PHL; 544 minutes. Local airport times.
- AA508: SJU 2026-11-20 08:30:00 → PHL 2026-11-20 11:39:00; layover at PHL: 135 minutes.
- AA595: PHL 2026-11-20 13:54:00 → ORD 2026-11-20 15:34:00.
2026-11-20 · one way · $200.00
- United Airlines UA2022 / UA2331: SJU 2026-11-20 08:05:00 → ORD 2026-11-20 14:38:00; 1 stop(s) via IAD; 513 minutes. Local airport times.
- UA2022: SJU 2026-11-20 08:05:00 → IAD 2026-11-20 11:09:00; layover at IAD: 126 minutes.
- UA2331: IAD 2026-11-20 13:15:00 → ORD 2026-11-20 14:38:00.
2026-11-20 → 2026-11-23 · $258.75
- Frontier Airlines F91015 / F92113: SJU 2026-11-20 07:28:00 → ORD 2026-11-20 14:12:00; 1 stop(s) via PHL; 524 minutes. Local airport times.
- F91015: SJU 2026-11-20 07:28:00 → PHL 2026-11-20 10:36:00; layover at PHL: 123 minutes.
- F92113: PHL 2026-11-20 12:39:00 → ORD 2026-11-20 14:12:00.
- Frontier Airlines F92112 / F91726: ORD 2026-11-23 16:42:00 → SJU 2026-11-24 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
- F92112: ORD 2026-11-23 16:42:00 → PHL 2026-11-23 20:04:00; layover at PHL: 95 minutes.
- F91726: PHL 2026-11-23 21:39:00 → SJU 2026-11-24 02:27:00.
2026-11-20 → 2026-11-23 · $258.75
- Frontier Airlines F92871 / F91441: SJU 2026-11-20 05:19:00 → ORD 2026-11-20 12:00:00; 1 stop(s) via ATL; 521 minutes. Local airport times.
- F92871: SJU 2026-11-20 05:19:00 → ATL 2026-11-20 08:26:00; layover at ATL: 131 minutes.
- F91441: ATL 2026-11-20 10:37:00 → ORD 2026-11-20 12:00:00.
- Frontier Airlines F92112 / F91726: ORD 2026-11-23 16:42:00 → SJU 2026-11-24 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
- F92112: ORD 2026-11-23 16:42:00 → PHL 2026-11-23 20:04:00; layover at PHL: 95 minutes.
- F91726: PHL 2026-11-23 21:39:00 → SJU 2026-11-24 02:27:00.
2026-11-27 → 2026-12-04 · $268.75
- Frontier Airlines F92871 / F91441: SJU 2026-11-27 05:19:00 → ORD 2026-11-27 12:00:00; 1 stop(s) via ATL; 521 minutes. Local airport times.
- F92871: SJU 2026-11-27 05:19:00 → ATL 2026-11-27 08:26:00; layover at ATL: 131 minutes.
- F91441: ATL 2026-11-27 10:37:00 → ORD 2026-11-27 12:00:00.
- Frontier Airlines F93346: ORD 2026-12-04 23:53:00 → SJU 2026-12-05 06:32:00; nonstop; 279 minutes. Local airport times.
2026-11-20 → 2026-11-23 · $268.75
- Frontier Airlines F94789: SJU 2026-11-20 22:26:00 → ORD 2026-11-21 01:33:00; nonstop; 307 minutes. Local airport times.
- Frontier Airlines F92112 / F91726: ORD 2026-11-23 16:42:00 → SJU 2026-11-24 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
- F92112: ORD 2026-11-23 16:42:00 → PHL 2026-11-23 20:04:00; layover at PHL: 95 minutes.
- F91726: PHL 2026-11-23 21:39:00 → SJU 2026-11-24 02:27:00.
2026-11-27 → 2026-12-04 · $268.75
- Frontier Airlines F91015 / F92113: SJU 2026-11-27 07:28:00 → ORD 2026-11-27 14:12:00; 1 stop(s) via PHL; 524 minutes. Local airport times.
- F91015: SJU 2026-11-27 07:28:00 → PHL 2026-11-27 10:36:00; layover at PHL: 123 minutes.
- F92113: PHL 2026-11-27 12:39:00 → ORD 2026-11-27 14:12:00.
- Frontier Airlines F93346: ORD 2026-12-04 23:53:00 → SJU 2026-12-05 06:32:00; nonstop; 279 minutes. Local airport times.
2026-11-27 → 2026-12-04 · $360.00
- DM DM1003 / DM5420: SJU 2026-11-27 16:24:00 → ORD 2026-11-27 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
- DM1003: SJU 2026-11-27 16:24:00 → PUJ 2026-11-27 17:25:00; layover at PUJ: 105 minutes.
- DM5420: PUJ 2026-11-27 19:10:00 → ORD 2026-11-27 22:20:00.
- DM DM5481 / DM1002: ORD 2026-12-04 05:45:00 → SJU 2026-12-04 15:03:00; 1 stop(s) via PUJ; 438 minutes. Local airport times.
- DM5481: ORD 2026-12-04 05:45:00 → PUJ 2026-12-04 12:30:00; layover at PUJ: 88 minutes.
- DM1002: PUJ 2026-12-04 13:58:00 → SJU 2026-12-04 15:03:00.
2026-11-27 → 2026-12-04 · $439.38
- American Airlines AA508 / AA595: SJU 2026-11-27 08:30:00 → ORD 2026-11-27 15:34:00; 1 stop(s) via PHL; 544 minutes. Local airport times.
- AA508: SJU 2026-11-27 08:30:00 → PHL 2026-11-27 11:39:00; layover at PHL: 135 minutes.
- AA595: PHL 2026-11-27 13:54:00 → ORD 2026-11-27 15:34:00.
- American Airlines AA2571: ORD 2026-12-04 23:00:00 → SJU 2026-12-05 05:36:00; nonstop; 276 minutes. Local airport times.
2026-11-20 → 2026-11-23 · $443.75
- American Airlines AA508 / AA595: SJU 2026-11-20 08:30:00 → ORD 2026-11-20 15:34:00; 1 stop(s) via PHL; 544 minutes. Local airport times.
- AA508: SJU 2026-11-20 08:30:00 → PHL 2026-11-20 11:39:00; layover at PHL: 135 minutes.
- AA595: PHL 2026-11-20 13:54:00 → ORD 2026-11-20 15:34:00.
- American Airlines AA2571: ORD 2026-11-23 23:00:00 → SJU 2026-11-24 05:36:00; nonstop; 276 minutes. Local airport times.
2026-11-27 → 2026-12-04 · $450.63
- United Airlines UA2022 / UA2331: SJU 2026-11-27 08:05:00 → ORD 2026-11-27 14:38:00; 1 stop(s) via IAD; 513 minutes. Local airport times.
- UA2022: SJU 2026-11-27 08:05:00 → IAD 2026-11-27 11:09:00; layover at IAD: 126 minutes.
- UA2331: IAD 2026-11-27 13:15:00 → ORD 2026-11-27 14:38:00.
- United Airlines UA1996: ORD 2026-12-04 08:52:00 → SJU 2026-12-04 15:40:00; nonstop; 288 minutes. Local airport times.
2026-11-27 → 2026-12-04 · $455.00
- United Airlines UA2089: SJU 2026-11-27 08:25:00 → ORD 2026-11-27 11:49:00; nonstop; 324 minutes. Local airport times.
- United Airlines UA1128 / UA2025: ORD 2026-12-04 13:00:00 → SJU 2026-12-04 22:22:00; 1 stop(s) via IAD; 442 minutes. Local airport times.
- UA1128: ORD 2026-12-04 13:00:00 → IAD 2026-12-04 16:03:00; layover at IAD: 86 minutes.
- UA2025: IAD 2026-12-04 17:29:00 → SJU 2026-12-04 22:22:00.
2026-11-20 → 2026-11-23 · $455.00
- United Airlines UA2022 / UA2331: SJU 2026-11-20 08:05:00 → ORD 2026-11-20 14:38:00; 1 stop(s) via IAD; 513 minutes. Local airport times.
- UA2022: SJU 2026-11-20 08:05:00 → IAD 2026-11-20 11:09:00; layover at IAD: 126 minutes.
- UA2331: IAD 2026-11-20 13:15:00 → ORD 2026-11-20 14:38:00.
- United Airlines UA695: ORD 2026-11-23 14:16:00 → SJU 2026-11-23 21:00:00; nonstop; 284 minutes. Local airport times.
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- Hawaii: for Christmas · for Thanksgiving · for spring break · for Presidents' Day weekend · in summer · for 4 days · for 5 days · for a week · for 10 days
- Mexico: for Christmas · for Thanksgiving · for spring break · for Presidents' Day weekend · for MLK weekend · in winter · in February · for 4 days · for 5 days · for a week
- The Caribbean: for Christmas · for spring break · for Presidents' Day weekend · in winter · in February · for 4 days · for 5 days · for a week
- Costa Rica: for Christmas · for spring break · in winter · for a week · for 10 days
- Central America: for Christmas · for spring break · in winter · for a week · for 10 days
- Europe: in summer · in May · in September · in December · for spring break · for Christmas · for a week · for 10 days · for two weeks
- Italy: in summer · in May · in June · in September · for Christmas · for a week · for 10 days · for two weeks
- Spain: in summer · in May · in September · for spring break · for a week · for 10 days
- Greece: in summer · in May · in June · in September · for a week · for 10 days · for two weeks
- Portugal: in summer · in May · in September · in winter · for 4 days · for a week · for 10 days
- Croatia: in summer · in June · in September · for a week · for 10 days
- Iceland: in summer · in winter · in September · for 4 days · for a week
- Scandinavia: in summer · in winter · in September · for 4 days · for a week · for 10 days
- Eastern Europe: in summer · in May · in September · in December · for a week · for 10 days
- England: in spring · in summer · in fall · for Christmas · for 4 days · for a week · for 10 days
- Scotland: in summer · in fall · for 4 days · for a week
- Japan: in April · in November · in winter · in summer · for a week · for 10 days · for two weeks
- 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
- 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
- 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
- The Midwest: for 3 days · for 4 days
- Anywhere: for Thanksgiving · for Christmas · for MLK weekend · for Presidents' Day 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 28, 2026. USD for the travelers shown. Search a trip for current prices.
Where to go from San Juan
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 | |
|---|---|---|---|---|---|
| Chicago (ORD) | Chicago's architecture, lakefront and deep-dish | Nonstop · American, United, Frontier | No matching fare saved | Jun 26 – Jul 3, 2027 (suggested) | Search these dates |
| Chicago (MDW) | Chicago Midway, the close-in airport | Nonstop · Southwest | No matching fare saved | Jun 26 – Jul 3, 2027 (suggested) | Search these dates |
| Minneapolis (MSP) | Minneapolis and St. Paul's lakes and the Mall of America | Nonstop · Delta, Sun Country | No matching fare saved | Jun 26 – Jul 3, 2027 (suggested) | Search these dates |
| Detroit (DTW) | Detroit's music history and the Motor City's comeback | Nonstop · Delta | No matching fare saved | Jun 26 – Jul 3, 2027 (suggested) | Search these dates |
| Saint Louis (STL) | St. Louis' Gateway Arch and barbecue | Nonstop · Southwest | No matching fare saved | Jun 26 – Jul 3, 2027 (suggested) | Search these dates |
| Kansas City (MCI) | Kansas City's barbecue and jazz | Nonstop · Southwest | No matching fare saved | Jun 26 – Jul 3, 2027 (suggested) | Search these dates |
| Cleveland (CLE) | Cleveland's Rock and Roll Hall of Fame and lakefront | 1 stop via Houston | $411 (airline $434) | Jun 26–Jul 3, 2027 | Check prices |
| Columbus (CMH) | Columbus' breweries and Short North arts district | Nonstop · Southwest | $413 (airline $436) | Jun 26–Jul 3, 2027 | Check prices |
| Cincinnati (CVG) | Cincinnati's riverfront and chili | 1 stop via Houston | $662 (airline $699) | Jun 26–Jul 3, 2027 | Check prices |
| Indianapolis (IND) | Indianapolis' speedway and canal walk | No nonstop seen | No matching fare saved | Jun 26 – Jul 3, 2027 (suggested) | Search these dates |
| Milwaukee (MKE) | Milwaukee's breweries and lakefront festivals | No nonstop seen | No matching fare saved | Jun 26 – Jul 3, 2027 (suggested) | Search these dates |
| Pittsburgh (PIT) | Pittsburgh's rivers, inclines and museums | No nonstop seen | No matching fare saved | Jun 26 – Jul 3, 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.
Keep exploring
Hotels in Chicago with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Chicago 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 Chicago: the 10 best neighborhoods, ranked · Chicago hotels where a family of four can share one room
Hotels with an Axel review in Chicago: Claridge House Chicago, Tapestry Collection by Hilton · Freehand Chicago · Warwick Allerton - Chicago · The Chicago Hotel Collection - Wrigleyville · The Chicago Hotel Collection Magnificent Mile Hotel & Suites · All 165 reviewed hotels in Chicago
For AI assistants
- This page: Flights from San Juan to the Midwest in summer. Round-trip fares from San Juan to the Midwest in summer: Chicago, Minneapolis, Detroit, Saint Louis, Kansas City and Cleveland and more. Saved fares for trips within June, July and August, with the cheapest 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.