Flight options

KelseyKelsey 🐨ORD · MDW
⭐ Sat 2/6 - Thu 2/11 · Top reco
5 nights · 4 PTO days
Everyone lands 8:34–8:59pm
Everyone leaves 6am

ORD

⭐ RecoAmerican $676
To GUA1:44pm → 8:34pm
Stop: 🤠 Dallas · 41m · 6h 50m total
Travel buddy: 🦒 Gina (same flight)
Home6am ☀️ → 3:50pm
Stop: 🌴 Miami · 3h 31m · 9h 50m total
⚠️ Tight connection
Only option for Feb 6–11 that met criteria!
AA1362 · AA2455 / AA352 · AA323 🔗 Round trip ↗
Fri 2/19 - Wed 2/24
5 nights · 4 PTO days
Everyone lands 11:54am–7:39pm
Everyone leaves 6am–2:48pm

ORD

American $619
To GUA6am ☀️ → 3:12pm
Stop: 🌴 Miami · 3h 03m · 9h 12m total
Travel buddy: 🦒 Gina (same flight)
Home1:20pm → 10:05pm 🌙
Stop: 🤠 Dallas · 2h 26m · 8h 45m total
AA3216 · AA2395 / AA1486 · AA1362 🔗 Round trip ↗
Fri 2/19 - Tue 2/23
4 nights · 3 PTO days
Everyone lands 12:16–3:12pm
Everyone leaves 6am–1:20pm

ORD

American $690
To GUA6am ☀️ → 3:12pm
Stop: 🌴 Miami · 3h 03m · 9h 12m total
Travel buddy: 🦒 Gina (same flight)
Home1:20pm → 10:05pm 🌙
Stop: 🤠 Dallas · 2h 26m · 8h 45m total
AA3216 · AA2395 / AA1486 · AA1362 🔗 Round trip ↗
Fri 2/19 - Thu 2/25
6 nights · 5 PTO days
Everyone lands 12:16–3:12pm
Everyone leaves 6am–1:20pm

ORD

American $655
To GUA6am ☀️ → 3:12pm
Stop: 🌴 Miami · 3h 03m · 9h 12m total
Travel buddy: 🦒 Gina (same flight)
Home1:20pm → 10:05pm 🌙
Stop: 🤠 Dallas · 2h 26m · 8h 45m total
AA3216 · AA2395 / AA1486 · AA1362 🔗 Round trip ↗
Sat 2/20 - Thu 2/25
5 nights · 4 PTO days
Everyone lands 11:54am–8:52pm
Everyone leaves 6am–3:01pm

ORD

American $672
To GUA8:10am → 12:38pm
Nonstop · 4h 28m total
Home3:01pm → 11:59pm 🌙
Stop: 🌴 Miami · 2h 30m · 8h 58m total
Nonstop out
AA599 / AA1620 · AA1918 🔗 Round trip ↗
Sat 2/20 - Wed 2/24
4 nights · 3 PTO days
Everyone lands 12:38–8:52pm
Everyone leaves 6am–1:20pm

ORD

American $672
To GUA8:10am → 12:38pm
Nonstop · 4h 28m total
Home1:20pm → 10:05pm 🌙
Stop: 🤠 Dallas · 2h 26m · 8h 45m total
AA599 / AA1486 · AA1362 🔗 Round trip ↗
Sat 2/20 - Fri 2/26
6 nights · 5 PTO days
Everyone lands 3:12–8:52pm
Everyone leaves 6am–1:20pm

ORD

American $676
To GUA7am ☀️ → 3:12pm
Stop: 🌴 Miami · 2h · 8h 12m total
Travel buddy: 🐆 CC (same flight)
Home1:20pm → 10:05pm 🌙
Stop: 🤠 Dallas · 2h 26m · 8h 45m total
AA1875 · AA2395 / AA1486 · AA1362 🔗 Round trip ↗