🇺🇸 Out Friday, back Sunday
Weekend getaways from Chicago, dated
Real round trips that fit a weekend: leave Thursday, Friday or Saturday and be back by Sunday or Monday. Click a trip to see those exact flights.
From $221 round trip
Weekend of Oct 23 – 25
2 nightsFort Lauderdale
Sat, Oct 24 → Mon, Oct 26
$221round trip
Direct · 3h 8m · Frontier Airlines
3 nights
Ontario
Fri, Oct 23 → Mon, Oct 26
$257round trip
1 stop · 5h 50m · Frontier Airlines
2 nightsTampa
Sat, Oct 24 → Mon, Oct 26
$257round trip
Direct · 5h 50m · Southwest Airlines
2 nightsPhiladelphia
Fri, Oct 23 → Sun, Oct 25
$283round trip
Direct · 2h 23m · Frontier Airlines
2 nightsBoston
Fri, Oct 23 → Sun, Oct 25
$352round trip
1 stop · 6h 14m · Frontier Airlines
1 nightToronto
Sat, Oct 24 → Sun, Oct 25
$521round trip
Direct · 1h 43m · Air Canada
From $189 round trip
Weekend of Oct 30 – Nov 1
From $184 round trip
Weekend of Nov 6 – 8
From $145 round trip
Weekend of Nov 13 – 15
Prices are round trip per person in USD, as last seen by our daily scan. Trips open on our booking partner (affiliate links — we may earn a commission at no cost to you).
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