Cheap Vacations in Kendall County

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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 $349, price is now $273 per person
$273
per person
Dec 14 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $2,268, price is now $831 per person
$831
per person
Dec 21 - Dec 24
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $654, price is now $462 per person
$462
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $800, price is now $573 per person
$573
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was $504, price is now $378 per person
$378
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was $768, price is now $579 per person
$579
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Houston (IAH) 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
Downtown Chicago
Save 100% on your flight
Price was $1,916, price is now $1,498 per person
$1,498
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was $483, price is now $379 per person
$379
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
Downtown Chicago
Price was $351, price is now $278 per person
$278
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Stay One Chicago

Stay One Chicago

4 out of 5
Downtown Chicago
Price was $785, price is now $626 per person
$626
per person
Dec 1 - Dec 3
found 12 hours ago
Roundtrip flight included
Houston (IAH) 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 $349, price is now $273 per person
$273
per person
Dec 14 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Price was $2,268, price is now $831 per person
$831
per person
Dec 21 - Dec 24
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $654, price is now $462 per person
$462
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $800, price is now $573 per person
$573
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Price was $435, price is now $325 per person
$325
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Price was $504, price is now $378 per person
$378
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Price was $577, price is now $435 per person
$435
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Eaglewood Resort and Spa

Eaglewood Resort and Spa

4 out of 5
Price was $428, price is now $325 per person
$325
per person
Dec 9 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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 $1,916, price is now $1,498 per person
$1,498
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Price was $483, price is now $379 per person
$379
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel

The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel

4 out of 5
Price was $427, price is now $335 per person
$335
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
Price was $351, price is now $278 per person
$278
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)

4-night Kendall County vacations

Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Price was $543, price is now $415 per person
$415
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Price was $1,771, price is now $693 per person
$693
per person
Dec 19 - Dec 23
found 10 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was $990, price is now $640 per person
$640
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Price was $863, price is now $589 per person
$589
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Price was $641, price is now $481 per person
$481
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Price was $768, price is now $579 per person
$579
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Price was $1,547, price is now $1,181 per person
$1,181
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Price was $699, price is now $539 per person
$539
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Save 100% on your flight
Price was $1,585, price is now $1,226 per person
$1,226
per person
Dec 23 - Dec 27
found 10 hours ago
Roundtrip flight included
Minneapolis (MSP) 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
Price was $749, price is now $587 per person
$587
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Price was $990, price is now $778 per person
$778
per person
Dec 19 - Dec 23
found 10 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Price was $655, price is now $515 per person
$515
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)

5-night Kendall County vacations

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $660, price is now $444 per person
$444
per person
Dec 17 - Dec 22
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $973, price is now $588 per person
$588
per person
Dec 17 - Dec 22
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Save 100% on your flight
Price was $725, price is now $492 per person
$492
per person
Dec 17 - Dec 22
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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 $681, price is now $472 per person
$472
per person
Dec 17 - Dec 22
found 1 day 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 $1,063, price is now $744 per person
$744
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $944, price is now $671 per person
$671
per person
Dec 10 - Dec 15
found 1 day 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 $740, price is now $527 per person
$527
per person
Dec 17 - Dec 22
found 1 day 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 $946, price is now $674 per person
$674
per person
Dec 17 - Dec 22
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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 $822, price is now $590 per person
$590
per person
Dec 17 - Dec 22
found 1 day 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 $831, price is now $609 per person
$609
per person
Dec 17 - Dec 22
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Price was $1,194, price is now $876 per person
$876
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
New Orleans (MSY) 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 $993, price is now $729 per person
$729
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)

6-7 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
Price was $646, price is now $452 per person
$452
per person
Dec 8 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was $1,143, price is now $664 per person
$664
per person
Dec 8 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Price was $1,096, price is now $703 per person
$703
per person
Dec 8 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Price was $934, price is now $644 per person
$644
per person
Dec 8 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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 $1,024, price is now $729 per person
$729
per person
Dec 10 - Dec 16
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Price was $1,383, price is now $998 per person
$998
per person
Dec 14 - Dec 21
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Price was $654, price is now $475 per person
$475
per person
Dec 8 - Dec 14
found 1 day ago
Roundtrip non-stop 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
Price was $998, price is now $734 per person
$734
per person
Dec 8 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
Price was $866, price is now $645 per person
$645
per person
Dec 8 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Price was $825, price is now $624 per person
$624
per person
Dec 8 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Price was $764, price is now $579 per person
$579
per person
Dec 8 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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.

Tue, Dec 8 - Sat, Dec 12
LAX
Los Angeles
ORD
Chicago
$139 Roundtrip, found 1 hour ago
$139
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Dec 8 from Los Angeles to Chicago, returning Sat, Dec 12, priced at $139 found 1 hour ago
Sat, Nov 21 - Tue, Nov 24
LAX
Los Angeles
ORD
Chicago
$212 Roundtrip, found 1 day ago
$212
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Nov 21 from Los Angeles to Chicago, returning Tue, Nov 24, priced at $212 found 1 day ago
Wed, Feb 24 - Sat, Feb 27
LAX
Los Angeles
MDW
Chicago
$237 Roundtrip, found 1 hour ago
$237
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Feb 24 from Los Angeles to Chicago, returning Sat, Feb 27, priced at $237 found 1 hour ago

Top rated hotels for your Kendall County vacation

Best Western Oswego Hotel

Best Western Oswego Hotel

2.5 out of 5
2055 Wiesbrook Dr Oswego IL
Free Cancellation
Reserve now, pay when you stay
8.87 mi from city center
$79 nightly
The price is $86 total per night
$86 total
Nov 8 - Nov 9
Total with taxes and fees
Located in Oswego, Best Western Oswego Hotel is within a 5-minute drive of Parkside Lanes and Aurora Skate Center.
Pool
Breakfast included
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
$64 nightly
The price is $71 total per night
$71 total
Nov 29 - Nov 30
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
$97 nightly
The price is $107 total per night
$107 total
Nov 4 - Nov 5
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
Don't see what you're looking for?
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.