Cheap Vacations in Cook County

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Cook County vacations

Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Chicago-Vernon Hills by IHG

Hotel Indigo Chicago-Vernon Hills by IHG

3.5 out of 5
Save 100% on your flight
Price was $682, price is now $482 per person
$482
per person
Jul 15 - Jul 22
found 11 hours ago
Roundtrip flight included
Columbus (CMH) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,239, price is now $1,401 per person
$1,401
per person
Jul 15 - Jul 22
found 11 hours ago
Roundtrip flight included
Columbus (CMH) to Chicago (ORD)
Holiday Inn Chicago North-Evanston by IHG

Holiday Inn Chicago North-Evanston by IHG

3 out of 5
Downtown Evanston
Save 100% on your flight
Price was $1,153, price is now $762 per person
$762
per person
Jul 15 - Jul 22
found 11 hours ago
Roundtrip flight included
Columbus (CMH) to Chicago (ORD)
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,422, price is now $1,614 per person
$1,614
per person
Jul 15 - Jul 22
found 11 hours ago
Roundtrip flight included
Columbus (CMH) 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 $2,174, price is now $1,479 per person
$1,479
per person
Jul 15 - Jul 22
found 11 hours ago
Roundtrip flight included
Columbus (CMH) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,303, price is now $895 per person
$895
per person
Jul 2 - Jul 6
found 9 hours ago
Roundtrip non-stop flight included
Amarillo (AMA) to Chicago (ORD)
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
West Lawn
Save 100% on your flight
Price was $988, price is now $687 per person
$687
per person
Jul 15 - Jul 22
found 11 hours ago
Roundtrip flight included
Columbus (CMH) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,089, price is now $765 per person
$765
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Chicago (ORD)
Chez Hotel Arlington Heights

Chez Hotel Arlington Heights

4 out of 5
Save 100% on your flight
Price was $1,128, price is now $797 per person
$797
per person
Jul 15 - Jul 22
found 11 hours ago
Roundtrip flight included
Columbus (CMH) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was $1,200, price is now $849 per person
$849
per person
Jul 2 - Jul 6
found 9 hours ago
Roundtrip non-stop flight included
Amarillo (AMA) to Chicago (ORD)

3-night Cook County vacations

Price found within the past 48 hours. Click for updated prices.
La Banque Hotel

La Banque Hotel

4 out of 5
Price was $794, price is now $597 per person
$597
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Price was $972, price is now $678 per person
$678
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Save 100% on your flight
Price was $1,089, price is now $765 per person
$765
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,265, price is now $901 per person
$901
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Price was $952, price is now $679 per person
$679
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) 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 $1,197, price is now $875 per person
$875
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Price was $867, price is now $674 per person
$674
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Price was $929, price is now $722 per person
$722
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Price was $1,256, price is now $984 per person
$984
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,507, price is now $1,187 per person
$1,187
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Chicago (ORD)
Hollywood Casino Aurora

Hollywood Casino Aurora

2 out of 5
Price was $879, price is now $697 per person
$697
per person
Jul 6 - Jul 9
found 20 hours ago
Roundtrip non-stop flight included
Columbus (CMH) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Price was $927, price is now $750 per person
$750
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Chicago (ORD)

4-night Cook County vacations

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Price was $1,054, price is now $752 per person
$752
per person
Jul 2 - Jul 6
found 9 hours ago
Roundtrip non-stop flight included
Amarillo (AMA) to Chicago (ORD)
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,423, price is now $956 per person
$956
per person
Jul 6 - Jul 10
found 1 hour ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was $1,303, price is now $895 per person
$895
per person
Jul 2 - Jul 6
found 9 hours ago
Roundtrip non-stop flight included
Amarillo (AMA) 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 $1,499, price is now $1,039 per person
$1,039
per person
Jul 9 - Jul 13
found 24 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Price was $1,200, price is now $849 per person
$849
per person
Jul 2 - Jul 6
found 9 hours ago
Roundtrip non-stop flight included
Amarillo (AMA) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,920, price is now $1,380 per person
$1,380
per person
Jul 9 - Jul 13
found 24 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
The Langham, Chicago

The Langham, Chicago

5 out of 5
Save 100% on your flight
Price was $2,066, price is now $1,491 per person
$1,491
per person
Jul 9 - Jul 13
found 24 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Price was $1,262, price is now $924 per person
$924
per person
Jul 6 - Jul 10
found 2 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Price was $1,078, price is now $803 per person
$803
per person
Jul 2 - Jul 6
found 9 hours ago
Roundtrip non-stop flight included
Amarillo (AMA) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Price was $1,130, price is now $844 per person
$844
per person
Jul 2 - Jul 6
found 9 hours ago
Roundtrip non-stop flight included
Amarillo (AMA) to Chicago (ORD)
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Price was $1,907, price is now $1,432 per person
$1,432
per person
Jul 6 - Jul 10
found 2 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Save 100% on your flight
Price was $2,184, price is now $1,641 per person
$1,641
per person
Jul 6 - Jul 10
found 1 hour ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)

5-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
Price was $1,078, price is now $816 per person
$816
per person
Jun 30 - Jul 5
found 13 hours ago
Roundtrip non-stop flight included
San Juan (SJU) 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 $1,625, price is now $1,207 per person
$1,207
per person
Jul 15 - Jul 20
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Price was $1,402, price is now $1,046 per person
$1,046
per person
Jul 15 - Jul 20
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,437, price is now $940 per person
$940
per person
Jun 30 - Jul 5
found 13 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,514, price is now $996 per person
$996
per person
Jun 30 - Jul 5
found 13 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,408, price is now $960 per person
$960
per person
Jun 30 - Jul 5
found 13 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Price was $1,299, price is now $957 per person
$957
per person
Jun 30 - Jul 5
found 13 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Price was $1,237, price is now $943 per person
$943
per person
Jun 30 - Jul 5
found 13 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Price was $1,210, price is now $930 per person
$930
per person
Jun 30 - Jul 5
found 13 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Price was $1,196, price is now $931 per person
$931
per person
Jun 30 - Jul 5
found 13 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
Price was $1,059, price is now $835 per person
$835
per person
Jun 30 - Jul 5
found 13 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Holiday Inn Express Chicago - Magnificent Mile by IHG

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 out of 5
Price was $1,058, price is now $849 per person
$849
per person
Jun 30 - Jul 5
found 13 hours ago
Roundtrip non-stop flight included
San Juan (SJU) 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 $1,158, price is now $751 per person
$751
per person
Jul 15 - Jul 22
found 11 hours ago
Roundtrip flight included
Columbus (CMH) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,947, price is now $1,088 per person
$1,088
per person
Jul 15 - Jul 22
found 11 hours ago
Roundtrip flight included
Columbus (CMH) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,731, price is now $991 per person
$991
per person
Jul 15 - Jul 22
found 11 hours ago
Roundtrip flight included
Columbus (CMH) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $2,016, price is now $1,193 per person
$1,193
per person
Jul 15 - Jul 22
found 11 hours ago
Roundtrip flight included
Columbus (CMH) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $2,239, price is now $1,401 per person
$1,401
per person
Jul 15 - Jul 22
found 11 hours ago
Roundtrip flight included
Columbus (CMH) 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 $1,905, price is now $1,197 per person
$1,197
per person
Jul 15 - Jul 22
found 11 hours ago
Roundtrip flight included
Columbus (CMH) 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 $1,850, price is now $1,166 per person
$1,166
per person
Jul 15 - Jul 22
found 11 hours ago
Roundtrip flight included
Columbus (CMH) to Chicago (ORD)
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
Save 100% on your flight
Price was $1,510, price is now $985 per person
$985
per person
Jul 15 - Jul 22
found 11 hours ago
Roundtrip flight included
Columbus (CMH) 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 $1,848, price is now $1,212 per person
$1,212
per person
Jul 15 - Jul 22
found 11 hours ago
Roundtrip flight included
Columbus (CMH) to Chicago (ORD)
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Save 100% on your flight
Price was $2,585, price is now $1,705 per person
$1,705
per person
Jul 15 - Jul 22
found 11 hours ago
Roundtrip flight included
Columbus (CMH) 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 $1,153, price is now $762 per person
$762
per person
Jul 15 - Jul 22
found 11 hours ago
Roundtrip flight included
Columbus (CMH) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $2,937, price is now $1,952 per person
$1,952
per person
Jul 15 - Jul 22
found 11 hours ago
Roundtrip flight included
Columbus (CMH) to Chicago (ORD)

Top places to visit in Cook County

649-36 Hammel Creek Dusted in Snow
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.

Fri, Jul 3 - Wed, Jul 8
LAX
Los Angeles
ORD
Chicago
$209 Roundtrip, found 3 days ago
$209
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Jul 3 from Los Angeles to Chicago, returning Wed, Jul 8, priced at $209 found 3 days ago
Wed, Sep 9 - Tue, Sep 15
LAX
Los Angeles
ORD
Chicago
$219 Roundtrip, found 1 hour ago
$219
Roundtrip
found 1 hour ago
Select United flight, departing Wed, Sep 9 from Los Angeles to Chicago, returning Tue, Sep 15, priced at $219 found 1 hour ago
Wed, Sep 9 - Tue, Sep 15
LAX
Los Angeles
ORD
Chicago
$219 Roundtrip, found 1 hour ago
$219
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Wed, Sep 9 from Los Angeles to Chicago, returning Tue, Sep 15, priced at $219 found 1 hour ago

Top rated hotels for your Cook County vacation

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
10.22 mi from city center
$135 nightly
The price is $161 total per night
$161 total
May 26 - May 27
Total with taxes and fees
With a stay at Congress Plaza Hotel, you'll be centrally located in Chicago, steps from Columbia College Chicago and Museum of Contemporary Photography.
Free WiFi
Restaurant
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
11.42 mi from city center
$199 nightly
The price is $236 total per night
$236 total
May 27 - May 28
Total with taxes and fees
With a stay at Hotel Riu Plaza Chicago, you'll be centrally located in Chicago, steps from Michigan Avenue and 10 minutes by foot from Chicago Riverwalk.
Breakfast included
Free WiFi
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Free Cancellation
Reserve now, pay when you stay
11.36 mi from city center
$138 nightly
The price is $164 total per night
$164 total
May 27 - May 28
Total with taxes and fees
Hotel Felix River North/Magnificent Mile is centrally located in Chicago, a 5-minute walk from Holy Name Cathedral and 10 minutes by foot from Chicago Water Tower.
Pet friendly
Free WiFi
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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.