Cheap Vacations in Cook County

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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
Downtown Chicago
Price was $555, price is now $383 per person
$383
per person
Oct 23 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,329, price is now $808 per person
$808
per person
Oct 1 - Oct 4
found 1 day 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
Downtown Chicago
Save 100% on your flight
Price was $1,347, price is now $858 per person
$858
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,285, price is now $838 per person
$838
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,098, price is now $736 per person
$736
per person
Oct 13 - Oct 17
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
Downtown Chicago
Save 100% on your flight
Price was $1,436, price is now $978 per person
$978
per person
Oct 1 - Oct 4
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
Downtown Chicago
Save 100% on your flight
Price was $1,003, price is now $689 per person
$689
per person
Oct 1 - Oct 4
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
Lakeview
Save 100% on your flight
Price was $1,431, price is now $996 per person
$996
per person
Oct 13 - Oct 17
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
Downtown Chicago
Save 100% on your flight
Price was $801, price is now $562 per person
$562
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $877, price is now $618 per person
$618
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $755, price is now $552 per person
$552
per person
Oct 1 - Oct 4
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 $1,329, price is now $808 per person
$808
per person
Oct 1 - Oct 4
found 1 day 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 $1,347, price is now $858 per person
$858
per person
Oct 1 - Oct 4
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 $1,436, price is now $978 per person
$978
per person
Oct 1 - Oct 4
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 $1,003, price is now $689 per person
$689
per person
Oct 1 - Oct 4
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 $801, price is now $562 per person
$562
per person
Oct 1 - Oct 4
found 1 day 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 $877, price is now $618 per person
$618
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Wade

The Wade

4.5 out of 5
Save 100% on your flight
Price was $1,215, price is now $865 per person
$865
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Save 100% on your flight
Price was $982, price is now $711 per person
$711
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Price was $870, price is now $636 per person
$636
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,025, price is now $755 per person
$755
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Price was $819, price is now $610 per person
$610
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

4-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 $914, price is now $572 per person
$572
per person
Oct 13 - Oct 17
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 $1,694, price is now $961 per person
$961
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,641, price is now $946 per person
$946
per person
Oct 13 - Oct 17
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 $1,033, price is now $631 per person
$631
per person
Oct 13 - Oct 17
found 1 day 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 $1,489, price is now $931 per person
$931
per person
Oct 13 - Oct 17
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 $1,535, price is now $982 per person
$982
per person
Oct 13 - Oct 17
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 $1,285, price is now $838 per person
$838
per person
Oct 2 - Oct 6
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 $1,966, price is now $1,300 per person
$1,300
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,098, price is now $736 per person
$736
per person
Oct 13 - Oct 17
found 1 day 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 $1,191, price is now $799 per person
$799
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Save 100% on your flight
Price was $1,154, price is now $791 per person
$791
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Save 100% on your flight
Price was $1,064, price is now $734 per person
$734
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

5-night Cook County vacations

Price found within the past 48 hours. Click for updated prices.
Chicago Marriott Southwest at Burr Ridge

Chicago Marriott Southwest at Burr Ridge

4 out of 5
Save 100% on your flight
Price was $991, price is now $745 per person
$745
per person
Oct 7 - Oct 12
found 19 hours 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 $1,945, price is now $1,171 per person
$1,171
per person
Oct 2 - Oct 7
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 $2,258, price is now $1,375 per person
$1,375
per person
Oct 9 - Oct 14
found 21 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 $2,570, price is now $1,725 per person
$1,725
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,674, price is now $1,134 per person
$1,134
per person
Oct 22 - Oct 27
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) 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 $2,197, price is now $1,531 per person
$1,531
per person
Oct 7 - Oct 12
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 $1,722, price is now $1,213 per person
$1,213
per person
Oct 15 - Oct 20
found 21 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 $1,208, price is now $866 per person
$866
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sentral Michigan Avenue

Sentral Michigan Avenue

4 out of 5
Save 100% on your flight
Price was $1,672, price is now $1,223 per person
$1,223
per person
Oct 15 - Oct 20
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Save 100% on your flight
Price was $2,900, price is now $2,156 per person
$2,156
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

3 out of 5
Save 100% on your flight
Price was $1,627, price is now $1,221 per person
$1,221
per person
Oct 3 - Oct 8
found 17 hours 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 $2,473, price is now $1,858 per person
$1,858
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

6-7 night Cook County vacations

Price found within the past 48 hours. Click for updated prices.
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,496, price is now $1,042 per person
$1,042
per person
Oct 20 - Oct 26
found 15 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $2,465, price is now $1,328 per person
$1,328
per person
Oct 20 - Oct 26
found 15 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $2,323, price is now $1,294 per person
$1,294
per person
Oct 20 - Oct 26
found 15 hours ago
Roundtrip flight included
Dallas (DAL) 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 $1,963, price is now $1,229 per person
$1,229
per person
Oct 20 - Oct 26
found 15 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $2,360, price is now $1,509 per person
$1,509
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Save 100% on your flight
Price was $4,163, price is now $2,714 per person
$2,714
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
Save 100% on your flight
Price was $2,004, price is now $1,335 per person
$1,335
per person
Oct 20 - Oct 26
found 15 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
Save 100% on your flight
Price was $1,669, price is now $1,130 per person
$1,130
per person
Oct 20 - Oct 26
found 15 hours ago
Roundtrip flight included
Dallas (DAL) 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 $2,327, price is now $1,582 per person
$1,582
per person
Oct 20 - Oct 26
found 15 hours ago
Roundtrip flight included
Dallas (DAL) 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 $1,786, price is now $1,263 per person
$1,263
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Save 100% on your flight
Price was $2,043, price is now $1,449 per person
$1,449
per person
Oct 20 - Oct 26
found 15 hours ago
Roundtrip flight included
Dallas (DAL) 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 $2,021, price is now $1,443 per person
$1,443
per person
Oct 20 - Oct 26
found 15 hours ago
Roundtrip flight included
Dallas (DAL) 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.

Wed, Oct 21 - Sat, Oct 24
LAX
Los Angeles
ORD
Chicago
$138 Roundtrip, found 1 day ago
$138
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Oct 21 from Los Angeles to Chicago, returning Sat, Oct 24, priced at $138 found 1 day ago
Fri, Nov 6 - Mon, Nov 9
LAX
Los Angeles
MDW
Chicago
$217 Roundtrip, found 15 hours ago
$217
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Fri, Nov 6 from Los Angeles to Chicago, returning Mon, Nov 9, priced at $217 found 15 hours ago
Thu, Nov 5 - Fri, Nov 6
LAX
Los Angeles
ORD
Chicago
$217 Roundtrip, just found
$217
Roundtrip
just found
Select United flight, departing Thu, Nov 5 from Los Angeles to Chicago, returning Fri, Nov 6, priced at $217 just found

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
$115 nightly
The price is $136 total per night
$136 total
Sep 7 - Sep 8
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
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
$122 nightly
The price is $144 total per night
$144 total
Sep 7 - Sep 8
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.
Pet friendly
Free WiFi
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
11.45 mi from city center
Get rates
With a stay at Kasa Magnificent Mile Chicago in Chicago (Downtown Chicago), you'll be a 5-minute walk from Michigan Avenue and 14 minutes by foot from Chicago Riverwalk.
Kitchen
Washer
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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.