Cheap Vacations in Kendall County

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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
Downtown Chicago
Price was $670, price is now $493 per person
$493
per person
Sep 8 - Sep 10
found 1 day ago
Roundtrip flight included
Albany (ALB) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,049, price is now $781 per person
$781
per person
Aug 27 - Aug 30
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
Price was $1,052, price is now $789 per person
$789
per person
Sep 14 - Sep 16
found 1 day ago
Roundtrip flight included
Albany (ALB) to Chicago (ORD)
The Chicago Hotel Collection - Wrigleyville

The Chicago Hotel Collection - Wrigleyville

3.5 out of 5
Lakeview
Save 100% on your flight
Price was $824, price is now $621 per person
$621
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,463, price is now $1,123 per person
$1,123
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,044, price is now $803 per person
$803
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Albany (ALB) to Chicago (ORD)
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Price was $987, price is now $760 per person
$760
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Albany (ALB) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was $1,150, price is now $890 per person
$890
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Albany (ALB) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was $970, price is now $752 per person
$752
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Albany (ALB) to Chicago (ORD)
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Price was $853, price is now $666 per person
$666
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Albany (ALB) to Chicago (ORD)

3-night Kendall County vacations

Price found within the past 48 hours. Click for updated prices.
Riverview Inn & Suites, an Ascend Collection Hotel

Riverview Inn & Suites, an Ascend Collection Hotel

3 out of 5
Price was $384, price is now $296 per person
$296
per person
Sep 13 - Sep 16
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 $843, price is now $506 per person
$506
per person
Sep 6 - Sep 9
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 $1,311, price is now $909 per person
$909
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
Price was $1,276, price is now $931 per person
$931
per person
Sep 14 - Sep 17
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 $1,049, price is now $781 per person
$781
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Chicago Hotel Collection - Wrigleyville

The Chicago Hotel Collection - Wrigleyville

3.5 out of 5
Save 100% on your flight
Price was $824, price is now $621 per person
$621
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
Price was $668, price is now $507 per person
$507
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Price was $579, price is now $441 per person
$441
per person
Sep 6 - Sep 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Save 100% on your flight
Price was $1,970, price is now $1,507 per person
$1,507
per person
Sep 16 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

The Langham, Chicago

5 out of 5
Save 100% on your flight
Price was $1,463, price is now $1,123 per person
$1,123
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Price was $1,044, price is now $803 per person
$803
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Albany (ALB) to Chicago (ORD)
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Price was $987, price is now $760 per person
$760
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Albany (ALB) to Chicago (ORD)

4-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 $631, price is now $417 per person
$417
per person
Aug 29 - Sep 2
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 $1,025, price is now $600 per person
$600
per person
Aug 29 - Sep 2
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 $2,590, price is now $1,684 per person
$1,684
per person
Aug 27 - Aug 31
found 19 hours 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 $1,008, price is now $676 per person
$676
per person
Aug 29 - Sep 2
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 $880, price is now $626 per person
$626
per person
Aug 29 - Sep 2
found 1 day 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 $873, price is now $627 per person
$627
per person
Aug 29 - Sep 2
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 $1,149, price is now $833 per person
$833
per person
Aug 27 - Aug 31
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $827, price is now $600 per person
$600
per person
Aug 29 - Sep 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $904, price is now $661 per person
$661
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $620, price is now $457 per person
$457
per person
Aug 29 - Sep 2
found 1 day 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 $2,724, price is now $2,016 per person
$2,016
per person
Sep 15 - Sep 19
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Save 100% on your flight
Price was $772, price is now $572 per person
$572
per person
Aug 29 - Sep 2
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 $739, price is now $469 per person
$469
per person
Aug 29 - Sep 3
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 $1,228, price is now $693 per person
$693
per person
Aug 29 - Sep 3
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 $1,477, price is now $885 per person
$885
per person
Sep 3 - Sep 8
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

The Langham, Chicago

5 out of 5
Save 100% on your flight
Price was $2,323, price is now $1,497 per person
$1,497
per person
Sep 4 - Sep 9
found 17 hours ago
Roundtrip flight included
New York (LGA) 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 $1,429, price is now $922 per person
$922
per person
Aug 29 - Sep 3
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 $1,723, price is now $1,113 per person
$1,113
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $994, price is now $684 per person
$684
per person
Sep 19 - Sep 24
found 1 day 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 $1,351, price is now $941 per person
$941
per person
Aug 29 - Sep 3
found 1 day 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 $1,007, price is now $722 per person
$722
per person
Aug 29 - Sep 3
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 $1,081, price is now $781 per person
$781
per person
Aug 29 - Sep 3
found 1 day 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 $2,277, price is now $1,656 per person
$1,656
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel 55 Chicago Downtown

Hotel 55 Chicago Downtown

4 out of 5
Save 100% on your flight
Price was $1,240, price is now $906 per person
$906
per person
Sep 19 - Sep 24
found 1 day 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.
The Westin Chicago Lombard

The Westin Chicago Lombard

4 out of 5
Save 100% on your flight
Price was $1,018, price is now $731 per person
$731
per person
Sep 1 - Sep 7
found 12 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $2,273, price is now $1,395 per person
$1,395
per person
Sep 1 - Sep 7
found 11 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $2,290, price is now $1,452 per person
$1,452
per person
Sep 1 - Sep 7
found 11 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,637, price is now $1,098 per person
$1,098
per person
Aug 28 - Sep 3
found 13 hours ago
Roundtrip flight included
New York (NYC) 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 $2,043, price is now $1,373 per person
$1,373
per person
Aug 28 - Sep 3
found 13 hours ago
Roundtrip flight included
New York (NYC) 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 $1,094, price is now $735 per person
$735
per person
Aug 28 - Sep 3
found 13 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)

The Langham, Chicago

5 out of 5
Save 100% on your flight
Price was $2,921, price is now $2,003 per person
$2,003
per person
Sep 1 - Sep 7
found 11 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $2,781, price is now $1,919 per person
$1,919
per person
Sep 1 - Sep 7
found 11 hours ago
Roundtrip flight included
New York (NYC) 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 $1,541, price is now $1,079 per person
$1,079
per person
Aug 28 - Sep 3
found 13 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $2,232, price is now $1,588 per person
$1,588
per person
Sep 1 - Sep 7
found 11 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Hilton Rosemont Chicago O'Hare

Hilton Rosemont Chicago O'Hare

3.5 out of 5
Save 100% on your flight
Price was $1,136, price is now $845 per person
$845
per person
Sep 1 - Sep 7
found 12 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
Price was $1,703, price is now $1,268 per person
$1,268
per person
Sep 1 - Sep 7
found 11 hours ago
Roundtrip flight included
New York (NYC) 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 4 hours ago
$163
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Mon, Aug 31 from Los Angeles to Chicago, returning Sat, Sep 5, priced at $163 found 4 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 20 hours ago
$810
Roundtrip
found 20 hours ago
Select British Airways flight, departing Wed, Aug 5 from Rome to Chicago, returning Sat, Sep 12, priced at $810 found 20 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
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.