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Boston (BOS)
Chicago
Wed 12/13
Sat 12/16
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Chicago vacation information
Top vacation (Flight+Hotel)
$312
Family vacation (Flight+Hotel)
$302
Romantic vacation (Flight+Hotel)
$332
Luxury vacation (Flight+Hotel)
$320
Budget vacation (Flight+Hotel)
$237
Cheap Chicago package deals
Ideal River North 1BR w/ Gym, Pool, W/D, near MM, by Blueground
$801
3 nights + flight
View Deal
Loftium | Peaceful Guest Suite/Garden Unit/Small kitchenette
$94
3 nights + flight
View Deal
Private Apartment With A Private Entrance To Our Cozy Newly Renovated Apartment
9.0
Excellent
2 reviews
$1,095
3 nights + flight
View Deal
Ukrainian Village 3 Bedroom Apartment
$1,735
3 nights + flight
View Deal
Full of Charm Studio Apartment Nearby Shops - Ashland 04
10.0
Excellent
1 review
$1,009
3 nights + flight
View Deal
Featured on the Travel Channel, 4 Bedroom 2 Bath in Wrigley Rooftop Building
10.0
Excellent
2 reviews
$5,918
3 nights + flight
View Deal
Lowest Rates! Spacious Duplex with Free Parking!
10.0
Excellent
6 reviews
$1,697
3 nights + flight
View Deal
Deluxe Oak Park 1BR w/ Lounge & Roof, nr Downtown, by Blueground
$773
3 nights + flight
View Deal
A Gem on Crystal Street
9.3
Excellent
3 reviews
$1,160
3 nights + flight
View Deal
Spacious Jr. Two Bedroom Suite with luxurious amenities and epicurian kitchen.
9.3
Excellent
3 reviews
$4,616
3 nights + flight
View Deal
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Chicago
Wed 12/13
Sat 12/16
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Wed 12/13
Wed 12/20
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2 travelers
Travelers
Unfortunately our partners limit offers to 6 travelers total. Please adjust your selection to continue.
Adults
2 adults selected
Children
0 children selected
Age Child 1
Under 2 years
Under 2 years
2 years
3 years
4 years
5 years
6 years
7 years
8 years
9 years
10 years
11 years
12 years
13 years
14 years
15 years
16 years
17 years
Age Child 2
Under 2 years
Under 2 years
2 years
3 years
4 years
5 years
6 years
7 years
8 years
9 years
10 years
11 years
12 years
13 years
14 years
15 years
16 years
17 years
Age Child 3
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Boston (BOS)
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Wed 12/13
Wed 12/20
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