Let Us Take You Away from Chicago with These Vacation Packages
Collapsed Enter the origin city of the trip.
Collapsed Enter the destination city of the trip.
Number of Stars
Carousel. Best fares on flights
1/30
3Night(s) Trip
FromChicago
ToCancun
-
Flights+Hotel
From
$550* Price subject to change
Viewed:a day ago
2/30
3Night(s) Trip
FromChicago
ToLas Vegas
-
Flights+Hotel
From
$271* Price subject to change
Viewed:13 hours ago
3/30
4Night(s) Trip
FromChicago
ToPunta Cana
-
Flights+Hotel
From
$641* Price subject to change
Viewed:a day ago
4/30
4Night(s) Trip
FromChicago
ToHonolulu
-
Flights+Hotel
From
$1,390* Price subject to change
Viewed:a day ago
5/30
4Night(s) Trip
FromChicago
ToCozumel
-
Flights+Hotel
From
$746* Price subject to change
Viewed:a day ago
6/30
2Night(s) Trip
FromChicago
ToLos Angeles
-
Flights+Hotel
From
$438* Price subject to change
Viewed:14 hours ago
7/30
6Night(s) Trip
FromChicago
ToCharleston
-
Flights+Hotel
From
$1,376* Price subject to change
Viewed:19 hours ago
8/30
5Night(s) Trip
FromChicago
ToLondon
-
Flights+Hotel
From
$1,050* Price subject to change
Viewed:a day ago
9/30
4Night(s) Trip
FromChicago
ToCabo San Lucas
-
Flights+Hotel
From
$1,054* Price subject to change
Viewed:a day ago
10/30
5Night(s) Trip
FromChicago
ToMiami
-
Flights+Hotel
From
$519* Price subject to change
Viewed:16 hours ago
11/30
4Night(s) Trip
FromChicago
ToPuerto Vallarta
-
Flights+Hotel
From
$913* Price subject to change
Viewed:a day ago
12/30
3Night(s) Trip
FromChicago
ToOranjestad, Aruba
-
Flights+Hotel
From
$873* Price subject to change
Viewed:a day ago
13/30
4Night(s) Trip
FromChicago
ToSan Juan
-
Flights+Hotel
From
$906* Price subject to change
Viewed:20 hours ago
14/30
3Night(s) Trip
FromChicago
ToFort Lauderdale
-
Flights+Hotel
From
$489* Price subject to change
Viewed:2 hours ago
15/30
3Night(s) Trip
FromChicago
ToKey West
-
Flights+Hotel
From
$925* Price subject to change
Viewed:14 hours ago
16/30
3Night(s) Trip
FromChicago
ToNassau
-
Flights+Hotel
From
$912* Price subject to change
Viewed:an hour ago
17/30
5Night(s) Trip
FromChicago
ToPhoenix
-
Flights+Hotel
From
$538* Price subject to change
Viewed:13 hours ago
18/30
8Night(s) Trip
FromChicago
ToFort Myers
-
Flights+Hotel
From
$1,139* Price subject to change
Viewed:10 hours ago
19/30
4Night(s) Trip
FromChicago
ToBoston
-
Flights+Hotel
From
$954* Price subject to change
Viewed:14 hours ago
20/30
2Night(s) Trip
FromChicago
ToSan Francisco
-
Flights+Hotel
From
$405* Price subject to change
Viewed:22 hours ago
21/30
2Night(s) Trip
FromChicago
ToNewark
-
Flights+Hotel
From
$417* Price subject to change
Viewed:12 hours ago
22/30
3Night(s) Trip
FromChicago
ToParis
-
Flights+Hotel
From
$1,031* Price subject to change
Viewed:23 hours ago
23/30
3Night(s) Trip
FromChicago
ToAustin
-
Flights+Hotel
From
$517* Price subject to change
Viewed:14 hours ago
24/30
5Night(s) Trip
FromChicago
ToReno
-
Flights+Hotel
From
$937* Price subject to change
Viewed:a day ago
25/30
8Night(s) Trip
FromChicago
ToPanama City
-
Flights+Hotel
From
$561* Price subject to change
Viewed:3 hours ago
26/30
3Night(s) Trip
FromChicago
ToTampa
-
Flights+Hotel
From
$533* Price subject to change
Viewed:13 hours ago
27/30
8Night(s) Trip
FromChicago
ToOrlando
-
Flights+Hotel
From
$478* Price subject to change
Viewed:a day ago
28/30
3Night(s) Trip
FromChicago
ToMontego Bay
-
Flights+Hotel
From
$662* Price subject to change
Viewed:14 hours ago
29/30
13Night(s) Trip
FromChicago
ToTokyo
-
Flights+Hotel
From
$1,951* Price subject to change
Viewed:a day ago
30/30
4Night(s) Trip
FromChicago
ToNew York
-
Flights+Hotel
From
$560* Price subject to change
Viewed:a day ago
Slide 1 of 8
*Average total price per person based on round trip flights and double occupancy hotel stays. Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply.