Cheap Vacations in Kendall County

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Kendall County vacations

Price found within the past 48 hours. Click for updated prices.
Eaglewood Resort and Spa

Eaglewood Resort and Spa

4 out of 5
Save 100% on your flight
Price was $559, price is now $403 per person
$403
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,325, price is now $818 per person
$818
per person
Nov 4 - Nov 9
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $953, price is now $635 per person
$635
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,037, price is now $701 per person
$701
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Grand Geneva Resort & Spa

Grand Geneva Resort & Spa

4 out of 5
Save 100% on your flight
Price was $749, price is now $517 per person
$517
per person
Oct 16 - Oct 18
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $730, price is now $508 per person
$508
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,183, price is now $828 per person
$828
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $788, price is now $554 per person
$554
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel 55 Chicago Downtown

Hotel 55 Chicago Downtown

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,339, price is now $988 per person
$988
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Chicago Hotel Collection River North

The Chicago Hotel Collection River North

3 out of 5
Downtown Chicago
Save 100% on your flight
Price was $581, price is now $429 per person
$429
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

3-night Kendall County vacations

Price found within the past 48 hours. Click for updated prices.
Eaglewood Resort and Spa

Eaglewood Resort and Spa

4 out of 5
Save 100% on your flight
Price was $559, price is now $403 per person
$403
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,365, price is now $866 per person
$866
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $927, price is now $616 per person
$616
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,037, price is now $701 per person
$701
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,181, price is now $814 per person
$814
per person
Oct 22 - Oct 25
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Save 100% on your flight
Price was $730, price is now $508 per person
$508
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $1,183, price is now $828 per person
$828
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $640, price is now $462 per person
$462
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Chicago Hotel Collection River North

The Chicago Hotel Collection River North

3 out of 5
Save 100% on your flight
Price was $581, price is now $429 per person
$429
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Save 100% on your flight
Price was $877, price is now $654 per person
$654
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

4 out of 5
Save 100% on your flight
Price was $767, price is now $573 per person
$573
per person
Oct 15 - Oct 18
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $712, price is now $534 per person
$534
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

4-night Kendall County vacations

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $794, price is now $549 per person
$549
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,525, price is now $936 per person
$936
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,872, price is now $1,168 per person
$1,168
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,555, price is now $1,005 per person
$1,005
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Save 100% on your flight
Price was $1,360, price is now $920 per person
$920
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $1,502, price is now $1,028 per person
$1,028
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Save 100% on your flight
Price was $1,373, price is now $950 per person
$950
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Save 100% on your flight
Price was $1,511, price is now $1,057 per person
$1,057
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $853, price is now $604 per person
$604
per person
Oct 21 - Oct 25
found 12 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3 out of 5
Save 100% on your flight
Price was $1,349, price is now $977 per person
$977
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $1,203, price is now $871 per person
$871
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay One Chicago

Stay One Chicago

4 out of 5
Save 100% on your flight
Price was $1,336, price is now $975 per person
$975
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

5-night Kendall County vacations

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $794, price is now $506 per person
$506
per person
Nov 4 - Nov 9
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,316, price is now $773 per person
$773
per person
Nov 4 - Nov 9
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,354, price is now $810 per person
$810
per person
Oct 28 - Nov 2
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,325, price is now $818 per person
$818
per person
Nov 4 - Nov 9
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $2,286, price is now $1,452 per person
$1,452
per person
Nov 6 - Nov 11
found 12 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $1,279, price is now $822 per person
$822
per person
Oct 28 - Nov 2
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $1,325, price is now $854 per person
$854
per person
Nov 4 - Nov 9
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Save 100% on your flight
Price was $1,291, price is now $844 per person
$844
per person
Oct 28 - Nov 2
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Save 100% on your flight
Price was $979, price is now $649 per person
$649
per person
Nov 4 - Nov 9
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Wade

The Wade

4.5 out of 5
Save 100% on your flight
Price was $924, price is now $621 per person
$621
per person
Nov 4 - Nov 9
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Save 100% on your flight
Price was $1,730, price is now $1,184 per person
$1,184
per person
Nov 6 - Nov 11
found 12 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Save 100% on your flight
Price was $901, price is now $621 per person
$621
per person
Nov 4 - Nov 9
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

6-7 night Kendall County vacations

Price found within the past 48 hours. Click for updated prices.
Sonesta Chicago O'Hare Airport Rosemont

Sonesta Chicago O'Hare Airport Rosemont

3 out of 5
Save 100% on your flight
Price was $796, price is now $555 per person
$555
per person
Nov 2 - Nov 9
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,650, price is now $970 per person
$970
per person
Nov 2 - Nov 9
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Save 100% on your flight
Price was $1,805, price is now $1,094 per person
$1,094
per person
Nov 2 - Nov 9
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $2,848, price is now $1,764 per person
$1,764
per person
Oct 20 - Oct 27
found 10 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $2,077, price is now $1,334 per person
$1,334
per person
Nov 2 - Nov 9
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $955, price is now $614 per person
$614
per person
Nov 2 - Nov 9
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $2,649, price is now $1,731 per person
$1,731
per person
Nov 2 - Nov 9
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Save 100% on your flight
Price was $1,793, price is now $1,187 per person
$1,187
per person
Nov 2 - Nov 9
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Save 100% on your flight
Price was $2,148, price is now $1,440 per person
$1,440
per person
Nov 2 - Nov 9
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay One Chicago

Stay One Chicago

4 out of 5
Save 100% on your flight
Price was $2,601, price is now $1,819 per person
$1,819
per person
Oct 20 - Oct 27
found 10 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Save 100% on your flight
Price was $1,204, price is now $846 per person
$846
per person
Nov 2 - Nov 9
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
Price was $1,448, price is now $1,018 per person
$1,018
per person
Nov 2 - Nov 9
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Top places to visit in Kendall County

A stone bridge over a calm river, surrounded by lush greenery and buildings.
FlightsFlightsHotelsHotels

Oswego

Oswego

Flight deals to Kendall County

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Tue, Oct 20 - Sat, Oct 24
LAX
Los Angeles
ORD
Chicago
$130 Roundtrip, found 13 hours ago
$130
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Tue, Oct 20 from Los Angeles to Chicago, returning Sat, Oct 24, priced at $130 found 13 hours ago
Fri, Oct 16 - Sun, Oct 18
LAX
Los Angeles
ORD
Chicago
$217 Roundtrip, found 2 days ago
$217
Roundtrip
found 2 days ago
Select United flight, departing Fri, Oct 16 from Los Angeles to Chicago, returning Sun, Oct 18, priced at $217 found 2 days ago
Tue, Oct 27 - Tue, Oct 27
LAX
Los Angeles
ORD
Chicago
$217 Roundtrip, found 12 hours ago
$217
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Tue, Oct 27 from Los Angeles to Chicago, returning Tue, Oct 27, priced at $217 found 12 hours ago

Top rated hotels for your Kendall County vacation

DoubleTree by Hilton Lisle Naperville

DoubleTree by Hilton Lisle Naperville

4 out of 5
3003 Corporate West Dr Naperville IL
Free Cancellation
Reserve now, pay when you stay
20.82 mi from city center
$86 nightly
The price is $96 total per night
$96 total
Oct 1 - Oct 2
Total with taxes and fees
Located in Naperville, DoubleTree by Hilton Lisle Naperville is in the business district, a 2-minute drive from Morton Arboretum and 6 minutes from College of Dupage.
Pool
Hot Tub
Chicago Club Inn & Suites

Chicago Club Inn & Suites

3 out of 5
630 Pasquinelli Dr Westmont IL
Free Cancellation
Reserve now, pay when you stay
28.13 mi from city center
$60 nightly
The price is $67 total per night
$67 total
Oct 13 - Oct 14
Total with taxes and fees
Located in Westmont, Chicago Club Inn & Suites is in the suburbs, a 5-minute drive from Oakbrook Center Mall and 8 minutes from Yorktown Shopping Center.
Pool
Breakfast included
SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard

2.5 out of 5
222 E 22nd Street Lombard IL
Free Cancellation
Reserve now, pay when you stay
26.63 mi from city center
$101 nightly
The price is $112 total per night
$112 total
Sep 28 - Sep 29
Total with taxes and fees
With a stay at SureStay Plus Hotel by Best Western Chicago Lombard in Lombard (Highland Hills), you'll be within a 10-minute drive of Oakbrook Center Mall and Yorktown Shopping Center.
Breakfast included
Parking included
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See all available properties in Kendall County
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.