🐨 KelseyORD · MDW
⭐ Sat 2/6 - Thu 2/11 · Top recommendation · 5 nights · 4 PTO days · Group land: 8:34–8:59pm · Group leave: 6am

ORD

⭐ RecoAmerican $676
To GUA1:44pm → 8:34pm
Stop: 🤠 Dallas · 41m · 6h50m total
Travel buddy: 🦒 Gina (same flight)
Home6am ☀️ → 3:50pm
Stop: 🌴 Miami · 3h31m · 9h50m total
Why this flight: Top pick — lands with the group at 8:34pm, same Dallas–Guatemala flight as Gina, shortest Dallas layover at 41m, under $700 with carry-on included.
AA1362 · AA2455 / AA352 · AA323 Round trip ↗
💲 Cheaper
Thu 2/18 - Tue 2/23
5 nights · 4 PTO days
Group land: 11:55am–11:25pm
Group leave: 6am–3pm

ORD

American $794
To GUA6:59am ☀️ → 2:01pm
Stop: 🤠 Dallas · 50m · 7h02m total
Home1:20pm → 10:05pm 🌙
Stop: 🤠 Dallas · 2h25m · 8h45m total
Higher price
AA377 · AA1013 / AA1486 · AA1362 Round trip ↗
Fri 2/19 - Wed 2/24
5 nights · 4 PTO days
Group land: 12:15–3:10pm
Group leave: 6am–4:10pm

ORD

American $619
To GUA6am ☀️ → 3:12pm
Stop: 🌴 Miami · 3h03m · 9h12m total
Travel buddy: 🦒 Gina (same flight)
Home1:20pm → 10:05pm 🌙
Stop: 🤠 Dallas · 2h25m · 8h45m total
Why this flight: Lowest Kelsey Feb 19 price at $605, with a 1:20pm home departure.
AA3216 · AA2395 / AA1486 · AA1362 Round trip ↗
Sat 2/20 - Thu 2/25
5 nights · 4 PTO days
Group land: 11:55am–8:50pm
Group leave: 6am–3:20pm

ORD

Delta $676
To GUA5:30am ☀️ → 12:45pm
Stop: 🍑 Atlanta · 1h35m · 7h15m total
Home2:15pm → 9:10pm
Stop: 🍑 Atlanta · 1h25m · 6h55m total
Why this flight: Only Delta option for Kelsey on Feb 20, via Atlanta, lands 12:45pm.
DL1264 · DL1830 / DL1831 · DL1139 Round trip ↗
⚡ Faster
Thu 2/18 - Tue 2/23
5 nights · 4 PTO days
Group land: 11:55am–11:25pm
Group leave: 6am–3pm

ORD

American $794
To GUA5am ☀️ → 12:16pm
Stop: 🌴 Miami · 1h · 7h16m total
Home1:20pm → 10:05pm 🌙
Stop: 🤠 Dallas · 2h25m · 8h45m total
Higher price; Early departure at 5am — at 5am or earlier; Not faster in total than Cheaper Feb 18 — 16h01m vs 15h47m
AA2984 · AA2241 / AA1486 · AA1362 Round trip ↗
Fri 2/19 - Wed 2/24
5 nights · 4 PTO days
Group land: 12:15–3:10pm
Group leave: 6am–4:10pm

ORD

Delta $754
To GUA7:10am ☀️ → 1:50pm
Stop: 🍑 Atlanta · 1h · 6h40m total
Home3:20pm → 10:20pm 🌙
Stop: 🍑 Atlanta · 1h25m · 7h total
Higher price
Why this flight: Faster Delta option at 6h40m total out, lands 1:50pm via Atlanta.
DL1247 · DL1776 / DL1821 · DL1139 Round trip ↗
Other options
Thu 2/18 - Tue 2/23
5 nights · 4 PTO days
Group land: 11:55am–11:25pm
Group leave: 6am–3pm

ORD

American $607
To GUA4pm → 11:23pm 🌙
Stop: 🤠 Dallas · 1h20m · 7h23m total
Home3:01pm → 11:59pm 🌙
Stop: 🌴 Miami · 2h30m · 8h58m total
Not lined up: lands 11:23pm + 11:59pm; $187 less
Why this flight: $187 less than the $794 Feb 18 options, afternoon departure; note the 11:23pm Guatemala arrival and 11:59pm home arrival.
AA353 · AA2455 / AA1620 · AA1918 Round trip ↗
Fri 2/19 - Wed 2/24
5 nights · 4 PTO days
Group land: 12:15–3:10pm
Group leave: 6am–4:10pm

ORD

American $619
To GUA6am ☀️ → 3:12pm
Stop: 🌴 Miami · 3h · 9h12m total
Home4:12pm → 12:47am 🌙
Stop: 🌴 Miami · 2h10m · 8h35m total
Not lined up: lands home 12:47am; later 4:12pm leave
AA3216 · AA2395 / AA1774 · AA2113 Round trip ↗
Sat 2/20 - Thu 2/25
5 nights · 4 PTO days
Group land: 11:55am–8:50pm
Group leave: 6am–3:20pm

ORD

American $672
To GUA8:10am → 12:38pm
Nonstop · 4h28m total
Home3:01pm → 11:59pm 🌙
Stop: 🌴 Miami · 2h30m · 8h58m total
Not lined up: lands home 11:59pm; nonstop out
Why this flight: Only nonstop flight for Kelsey on Feb 20 at 4h28m, lands 12:38pm.
AA599 / AA1620 · AA1918 Round trip ↗
📅 More dates – shorter / longer stay
Fri 2/19 - Thu 2/25
6 nights · 5 PTO days
6 nights

ORD

American $655
To GUA6am ☀️ → 3:12pm
Stop: 🌴 Miami · 3h · 9h12m total
Travel buddy: 🦒 Gina (same flight)
Home1:20pm → 10:05pm 🌙
Stop: 🤠 Dallas · 2h25m · 8h45m total
AA3216 · AA2395 / AA1486 · AA1362 Round trip ↗
Fri 2/19 - Tue 2/23
4 nights · 3 PTO days
4 nights

ORD

American $690
To GUA6am ☀️ → 3:12pm
Stop: 🌴 Miami · 3h · 9h12m total
Travel buddy: 🦒 Gina (same flight)
Home1:20pm → 10:05pm 🌙
Stop: 🤠 Dallas · 2h25m · 8h45m total
AA3216 · AA2395 / AA1486 · AA1362 Round trip ↗
Sat 2/20 - Wed 2/24
4 nights · 3 PTO days
4 nights

ORD

American $672
To GUA8:10am → 12:38pm
Nonstop · 4h28m total
Home1:20pm → 10:05pm 🌙
Stop: 🤠 Dallas · 2h25m · 8h45m total
Why this flight: Only nonstop flight for Kelsey on Feb 20 at 4h28m, lands 12:38pm, 1:20pm home departure via Dallas.
AA599 / AA1486 · AA1362 Round trip ↗
Sat 2/20 - Fri 2/26
6 nights · 5 PTO days
6 nights

ORD

American $688
To GUA7am ☀️ → 3:12pm
Stop: 🌴 Miami · 2h · 8h12m total
Travel buddy: 🦒 Gina (same flight)
Home1:20pm → 10:05pm 🌙
Stop: 🤠 Dallas · 2h25m · 8h45m total
Why this flight: 6-night version of the Feb 20 trip, 7am departure, lands 3:12pm.
AA1875 · AA2395 / AA1486 · AA1362 Round trip ↗