Cheap Vacations in Cook County

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Cook County vacations

Price found within the past 48 hours. Click for updated prices.
Grand Geneva Resort & Spa

Grand Geneva Resort & Spa

4 out of 5
Price was $730, price is now $547 per person
$547
per person
Sep 3 - Sep 5
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,829, price is now $1,212 per person
$1,212
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,368, price is now $972 per person
$972
per person
Aug 20 - Aug 23
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 $871, price is now $628 per person
$628
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Albany (ALB) to Chicago (ORD)
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was $940, price is now $701 per person
$701
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Albany (ALB) to Chicago (ORD)
Nobu Hotel Chicago

Nobu Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,952, price is now $1,464 per person
$1,464
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was $906, price is now $700 per person
$700
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Albany (ALB) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,462, price is now $1,129 per person
$1,129
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Albany (ALB) 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 $984, price is now $762 per person
$762
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Albany (ALB) to Chicago (ORD)
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Save 100% on your flight
Price was $950, price is now $736 per person
$736
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)

3-night Cook 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
Price was $871, price is now $628 per person
$628
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Albany (ALB) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,172, price is now $803 per person
$803
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,240, price is now $860 per person
$860
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,067, price is now $740 per person
$740
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,368, price is now $972 per person
$972
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Albany (ALB) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $1,081, price is now $805 per person
$805
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Price was $940, price is now $701 per person
$701
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Albany (ALB) to Chicago (ORD)
The Langham, Chicago

The Langham, Chicago

5 out of 5
Save 100% on your flight
Price was $1,560, price is now $1,175 per person
$1,175
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Price was $906, price is now $700 per person
$700
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Albany (ALB) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,462, price is now $1,129 per person
$1,129
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Albany (ALB) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Price was $984, price is now $762 per person
$762
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Albany (ALB) to Chicago (ORD)
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Save 100% on your flight
Price was $950, price is now $736 per person
$736
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)

4-night Cook County vacations

Price found within the past 48 hours. Click for updated prices.
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

4 out of 5
Price was $823, price is now $631 per person
$631
per person
Aug 23 - Aug 27
found 1 day 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 $1,706, price is now $1,159 per person
$1,159
per person
Aug 26 - Aug 30
found 17 hours 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 $1,563, price is now $1,067 per person
$1,067
per person
Sep 3 - Sep 7
found 22 hours ago
Roundtrip flight included
Albany (ALB) 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 $1,167, price is now $834 per person
$834
per person
Aug 27 - Aug 31
found 17 hours ago
Roundtrip flight included
Albany (ALB) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,401, price is now $1,017 per person
$1,017
per person
Sep 3 - Sep 7
found 22 hours ago
Roundtrip flight included
Albany (ALB) 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 $1,678, price is now $1,226 per person
$1,226
per person
Sep 3 - Sep 7
found 22 hours ago
Roundtrip flight included
Albany (ALB) to Chicago (ORD)
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,067, price is now $798 per person
$798
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $1,385, price is now $1,039 per person
$1,039
per person
Sep 3 - Sep 7
found 22 hours ago
Roundtrip flight included
Albany (ALB) 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 $1,194, price is now $900 per person
$900
per person
Sep 2 - Sep 6
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
Price was $980, price is now $748 per person
$748
per person
Aug 27 - Aug 31
found 17 hours ago
Roundtrip flight included
Albany (ALB) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Save 100% on your flight
Price was $1,021, price is now $781 per person
$781
per person
Sep 3 - Sep 7
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Save 100% on your flight
Price was $1,087, price is now $835 per person
$835
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)

5-night Cook County vacations

Price found within the past 48 hours. Click for updated prices.
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
Save 100% on your flight
Price was $939, price is now $688 per person
$688
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,490, price is now $966 per person
$966
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,521, price is now $989 per person
$989
per person
Aug 17 - Aug 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,829, price is now $1,212 per person
$1,212
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $3,131, price is now $2,079 per person
$2,079
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,685, price is now $1,151 per person
$1,151
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,421, price is now $987 per person
$987
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,213, price is now $870 per person
$870
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
Price was $1,777, price is now $1,301 per person
$1,301
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $2,270, price is now $1,672 per person
$1,672
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,173, price is now $867 per person
$867
per person
Aug 19 - Aug 24
found 8 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
Save 100% on your flight
Price was $1,066, price is now $794 per person
$794
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)

6-7 night Cook 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 $1,094, price is now $716 per person
$716
per person
Aug 28 - Sep 3
found 4 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $2,346, price is now $1,410 per person
$1,410
per person
Sep 1 - Sep 8
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,607, price is now $1,061 per person
$1,061
per person
Aug 28 - Sep 3
found 4 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $1,941, price is now $1,317 per person
$1,317
per person
Aug 28 - Sep 3
found 4 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $1,472, price is now $1,027 per person
$1,027
per person
Aug 28 - Sep 3
found 4 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $1,229, price is now $892 per person
$892
per person
Aug 28 - Sep 3
found 4 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,484, price is now $1,079 per person
$1,079
per person
Sep 1 - Sep 8
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $2,089, price is now $1,541 per person
$1,541
per person
Sep 1 - Sep 8
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,320, price is now $1,004 per person
$1,004
per person
Aug 28 - Sep 3
found 4 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $1,002, price is now $771 per person
$771
per person
Aug 28 - Sep 3
found 4 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $2,007, price is now $1,546 per person
$1,546
per person
Sep 1 - Sep 8
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown Riverwalk

Hilton Garden Inn Chicago Downtown Riverwalk

3 out of 5
Save 100% on your flight
Price was $1,151, price is now $900 per person
$900
per person
Aug 28 - Sep 3
found 4 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

Top places to visit in Cook County

A river flowing through a forest with autumn-colored trees and fallen leaves.
FlightsFlightsHotelsHotels

Tinley Park

Tinley Park

Flight deals to Cook County

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

Mon, Aug 31 - Fri, Sep 4
LAX
Los Angeles
ORD
Chicago
$129 Roundtrip, found 8 hours ago
$129
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Mon, Aug 31 from Los Angeles to Chicago, returning Fri, Sep 4, priced at $129 found 8 hours ago
Fri, Sep 18 - Tue, Sep 22
LAX
Los Angeles
MDW
Chicago
$237 Roundtrip, found 4 hours ago
$237
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Fri, Sep 18 from Los Angeles to Chicago, returning Tue, Sep 22, priced at $237 found 4 hours ago
Thu, Oct 15 - Wed, Oct 21
LAX
Los Angeles
ORD
Chicago
$237 Roundtrip, found 10 hours ago
$237
Roundtrip
found 10 hours ago
Select United flight, departing Thu, Oct 15 from Los Angeles to Chicago, returning Wed, Oct 21, priced at $237 found 10 hours ago

Top rated hotels for your Cook County vacation

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
18.76 mi from city center
$189 nightly
The price is $215 total per night
$215 total
Aug 6 - Aug 7
Total with taxes and fees
With a stay at Hyatt Regency O'Hare Chicago in Rosemont, you'll be connected to the convention center, a 5-minute walk from Donald E. Stephens Convention Center and 9 minutes by foot from Rosemont Theatre.
Free airport shuttle
Pet friendly
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Free Cancellation
Reserve now, pay when you stay
12.15 mi from city center
$190 nightly
The price is $226 total per night
$226 total
Jul 19 - Jul 20
Total with taxes and fees
You'll be centrally located in Chicago with a stay at The Chicago Hotel Collection Ambassador Gold Coast, within a 15-minute walk of Oak Street Beach and Chicago History Museum.
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
11.59 mi from city center
$254 nightly
The price is $302 total per night
$302 total
Aug 9 - Aug 10
Total with taxes and fees
Located in Chicago (Downtown Chicago), The Wade is within a 10-minute walk of Lake Michigan and Michigan Avenue.
Pool
Pet friendly
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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.