Cheap Vacations in Kendall County

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Kendall County vacations

Price found within the past 48 hours. Click for updated prices.
Motel Edgebrook Chicago North Shore by OYO

Motel Edgebrook Chicago North Shore by OYO

2 out of 5
Forest Glen
Save 100% on your flight
Price was $923, price is now $651 per person
$651
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,054, price is now $706 per person
$706
per person
Sep 9 - Sep 12
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was $1,063, price is now $766 per person
$766
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Albuquerque (ABQ) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,134, price is now $835 per person
$835
per person
Aug 28 - Aug 31
found 20 hours ago
Roundtrip flight included
Charlotte (CLT) 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 $1,420, price is now $1,063 per person
$1,063
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Albuquerque (ABQ) to Chicago (ORD)

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,046, price is now $1,579 per person
$1,579
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Price was $1,114, price is now $887 per person
$887
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Albuquerque (ABQ) to Chicago (ORD)
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,820, price is now $1,450 per person
$1,450
per person
Sep 10 - Sep 13
found 11 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,256, price is now $1,010 per person
$1,010
per person
Sep 16 - Sep 19
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Price was $1,057, price is now $854 per person
$854
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Albuquerque (ABQ) to Chicago (ORD)

3-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 $1,054, price is now $706 per person
$706
per person
Sep 9 - Sep 12
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $1,028, price is now $735 per person
$735
per person
Sep 10 - Sep 13
found 11 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Price was $1,063, price is now $766 per person
$766
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Albuquerque (ABQ) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,134, price is now $835 per person
$835
per person
Aug 28 - Aug 31
found 20 hours ago
Roundtrip flight included
Charlotte (CLT) 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 $1,420, price is now $1,063 per person
$1,063
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Albuquerque (ABQ) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,473, price is now $1,110 per person
$1,110
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)

The Langham, Chicago

5 out of 5
Save 100% on your flight
Price was $1,725, price is now $1,328 per person
$1,328
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Price was $1,114, price is now $887 per person
$887
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Albuquerque (ABQ) to Chicago (ORD)
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Save 100% on your flight
Price was $1,820, price is now $1,450 per person
$1,450
per person
Sep 10 - Sep 13
found 11 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $1,256, price is now $1,010 per person
$1,010
per person
Sep 16 - Sep 19
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Price was $1,057, price is now $854 per person
$854
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Albuquerque (ABQ) to Chicago (ORD)
ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments

2 out of 5
Save 100% on your flight
Price was $1,725, price is now $1,400 per person
$1,400
per person
Sep 10 - Sep 13
found 11 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)

4-night Kendall County vacations

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Price was $1,074, price is now $833 per person
$833
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,485, price is now $950 per person
$950
per person
Sep 9 - Sep 13
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,757, price is now $1,215 per person
$1,215
per person
Sep 12 - Sep 16
found 6 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $1,292, price is now $944 per person
$944
per person
Aug 27 - Aug 31
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $2,581, price is now $1,971 per person
$1,971
per person
Sep 12 - Sep 16
found 6 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
Price was $1,470, price is now $1,123 per person
$1,123
per person
Sep 12 - Sep 16
found 6 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)

The Langham, Chicago

5 out of 5
Save 100% on your flight
Price was $2,046, price is now $1,579 per person
$1,579
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,555, price is now $1,231 per person
$1,231
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,421, price is now $1,148 per person
$1,148
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
Price was $1,164, price is now $942 per person
$942
per person
Sep 3 - Sep 7
found 13 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG

3.5 out of 5
Price was $1,088, price is now $881 per person
$881
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,583, price is now $1,283 per person
$1,283
per person
Aug 27 - Aug 31
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

5-night Kendall County vacations

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Save 100% on your flight
Price was $1,086, price is now $832 per person
$832
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $2,296, price is now $1,443 per person
$1,443
per person
Sep 17 - Sep 22
found 10 hours ago
Roundtrip flight included
Philadelphia (PHL) 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 $1,330, price is now $871 per person
$871
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 $1,620, price is now $1,145 per person
$1,145
per person
Sep 17 - Sep 22
found 10 hours ago
Roundtrip flight included
Philadelphia (PHL) 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 $1,597, price is now $1,146 per person
$1,146
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 $1,369, price is now $1,024 per person
$1,024
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Save 100% on your flight
Price was $1,318, price is now $992 per person
$992
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Save 100% on your flight
Price was $1,244, price is now $944 per person
$944
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,280, price is now $976 per person
$976
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Save 100% on your flight
Price was $1,215, price is now $932 per person
$932
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Save 100% on your flight
Price was $1,338, price is now $1,053 per person
$1,053
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
River Hotel

River Hotel

4 out of 5
Price was $1,138, price is now $906 per person
$906
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

6-7 night Kendall County vacations

Price found within the past 48 hours. Click for updated prices.
Motel Edgebrook Chicago North Shore by OYO

Motel Edgebrook Chicago North Shore by OYO

2 out of 5
Save 100% on your flight
Price was $923, price is now $651 per person
$651
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $2,643, price is now $1,548 per person
$1,548
per person
Sep 8 - Sep 15
found 10 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,679, price is now $1,102 per person
$1,102
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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 $1,817, price is now $1,250 per person
$1,250
per person
Sep 8 - Sep 15
found 10 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
Save 100% on your flight
Price was $1,234, price is now $851 per person
$851
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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 $1,776, price is now $1,236 per person
$1,236
per person
Sep 8 - Sep 15
found 10 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
River Hotel

River Hotel

4 out of 5
Save 100% on your flight
Price was $1,477, price is now $1,040 per person
$1,040
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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 $2,050, price is now $1,445 per person
$1,445
per person
Sep 8 - Sep 15
found 10 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Save 100% on your flight
Price was $1,330, price is now $939 per person
$939
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
Save 100% on your flight
Price was $1,478, price is now $1,046 per person
$1,046
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Holiday Inn Chicago North-Evanston by IHG

Holiday Inn Chicago North-Evanston by IHG

3 out of 5
Save 100% on your flight
Price was $1,429, price is now $1,024 per person
$1,024
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
Save 100% on your flight
Price was $1,518, price is now $1,088 per person
$1,088
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)

Top places to visit in Kendall County

A calm lake with reflections of trees and sky, surrounded by greenery and a clear blue sky.
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Yorkville

Yorkville

Flight deals to Kendall County

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

Mon, Aug 31 - Sat, Sep 5
LAX
Los Angeles
ORD
Chicago
$163 Roundtrip, found 9 hours ago
$163
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Mon, Aug 31 from Los Angeles to Chicago, returning Sat, Sep 5, priced at $163 found 9 hours ago
Sat, Sep 12 - Sat, Sep 26
LAX
Los Angeles
MDW
Chicago
$237 Roundtrip, found 6 days ago
$237
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Sep 12 from Los Angeles to Chicago, returning Sat, Sep 26, priced at $237 found 6 days ago
Wed, Aug 5 - Sat, Sep 12
FCO
Rome
ORD
Chicago
$810 Roundtrip, found 1 day ago
$810
Roundtrip
found 1 day ago
Select British Airways flight, departing Wed, Aug 5 from Rome to Chicago, returning Sat, Sep 12, priced at $810 found 1 day 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
Aug 2 - Aug 3
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
Red Roof Inn PLUS+ Chicago - Willowbrook

Red Roof Inn PLUS+ Chicago - Willowbrook

2.5 out of 5
7535 Kingery Highway Willowbrook IL
Free Cancellation
Reserve now, pay when you stay
27.07 mi from city center
$59 nightly
The price is $66 total per night
$66 total
Aug 2 - Aug 3
Total with taxes and fees
With a stay at Red Roof Inn PLUS+ Chicago - Willowbrook in Willowbrook, you'll be in the suburbs, within a 10-minute drive of Oakbrook Center Mall and Willowbrook Community Park.
Pet friendly
Parking included
Embassy Suites by Hilton Chicago Lombard Oak Brook

Embassy Suites by Hilton Chicago Lombard Oak Brook

3.5 out of 5
707 E Butterfield Road Lombard IL
Free Cancellation
Reserve now, pay when you stay
26.83 mi from city center
$130 nightly
The price is $145 total per night
$145 total
Aug 2 - Aug 3
Total with taxes and fees
With a stay at Embassy Suites by Hilton Chicago Lombard Oak Brook in Lombard, you'll be in the business district, within a 5-minute drive of Oakbrook Center Mall and Yorktown Shopping Center.
Pool
Breakfast included
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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.