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 $410, price is now $340 per person
$340
per person
Dec 11 - Dec 13
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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 $1,922, price is now $1,359 per person
$1,359
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $958, price is now $721 per person
$721
per person
Nov 25 - Nov 28
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $1,002, price is now $768 per person
$768
per person
Nov 27 - Nov 29
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $860, price is now $663 per person
$663
per person
Nov 27 - Nov 30
found 11 hours ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was $853, price is now $662 per person
$662
per person
Nov 25 - Nov 28
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $930, price is now $744 per person
$744
per person
Nov 25 - Nov 28
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was $720, price is now $580 per person
$580
per person
Nov 25 - Nov 28
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was $1,277, price is now $1,040 per person
$1,040
per person
Nov 27 - Nov 29
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Sonesta Chicago O'Hare Airport Rosemont

Sonesta Chicago O'Hare Airport Rosemont

3 out of 5
Price was $471, price is now $388 per person
$388
per person
Nov 26 - Nov 29
found 24 hours ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)

3-night Cook County vacations

Price found within the past 48 hours. Click for updated prices.
The Chicago Hotel Collection River North

The Chicago Hotel Collection River North

3 out of 5
Price was $470, price is now $381 per person
$381
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,527, price is now $1,078 per person
$1,078
per person
Nov 18 - Nov 21
found 1 day ago
Roundtrip flight included
Washington (DCA) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Price was $1,055, price is now $756 per person
$756
per person
Dec 3 - Dec 6
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
The Glen Club

The Glen Club

4 out of 5
Price was $620, price is now $458 per person
$458
per person
Dec 7 - Dec 10
found 9 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
Price was $958, price is now $721 per person
$721
per person
Nov 25 - Nov 28
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Price was $860, price is now $663 per person
$663
per person
Nov 27 - Nov 30
found 11 hours ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Price was $853, price is now $662 per person
$662
per person
Nov 25 - Nov 28
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Price was $930, price is now $744 per person
$744
per person
Nov 25 - Nov 28
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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 $720, price is now $580 per person
$580
per person
Nov 25 - Nov 28
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Sentral Michigan Avenue

Sentral Michigan Avenue

4 out of 5
Price was $740, price is now $602 per person
$602
per person
Nov 27 - Nov 30
found 11 hours ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Price was $844, price is now $687 per person
$687
per person
Nov 27 - Nov 30
found 11 hours ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Price was $901, price is now $734 per person
$734
per person
Nov 18 - Nov 21
found 1 day ago
Roundtrip flight included
Washington (DCA) to Chicago (ORD)

4-night Cook County vacations

Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Price was $507, price is now $399 per person
$399
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $953, price is now $653 per person
$653
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
The Glen Club

The Glen Club

4 out of 5
Save 100% on your flight
Price was $629, price is now $431 per person
$431
per person
Dec 4 - Dec 8
found 10 hours ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,922, price is now $1,359 per person
$1,359
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was $1,124, price is now $816 per person
$816
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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 $1,083, price is now $795 per person
$795
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Price was $1,120, price is now $859 per person
$859
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
Price was $626, price is now $482 per person
$482
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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 $840, price is now $657 per person
$657
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,062, price is now $846 per person
$846
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Price was $1,023, price is now $823 per person
$823
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Price was $538, price is now $435 per person
$435
per person
Dec 10 - Dec 14
found 2 days ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)

5-night Cook County vacations

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

Kinzie Hotel

4 out of 5
Save 100% on your flight
Price was $796, price is now $568 per person
$568
per person
Dec 11 - Dec 16
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $2,466, price is now $1,747 per person
$1,747
per person
Nov 24 - Nov 29
found 8 hours ago
Roundtrip flight included
Washington (DCA) to Chicago (ORD)
Hotel Chicago Downtown, Autograph Collection by Marriott

Hotel Chicago Downtown, Autograph Collection by Marriott

4 out of 5
Price was $1,094, price is now $955 per person
$955
per person
Nov 24 - Nov 29
found 8 hours ago
Roundtrip flight included
Washington (DCA) to Chicago (ORD)
The Inn on Sheridan

The Inn on Sheridan

3.5 out of 5
Price was $845, price is now $765 per person
$765
per person
Nov 24 - Nov 29
found 8 hours ago
Roundtrip flight included
Washington (DCA) to Chicago (ORD)
William Tell Hotel MOD Collection by Sonesta

William Tell Hotel MOD Collection by Sonesta

3.5 out of 5
Price was $782, price is now $714 per person
$714
per person
Nov 24 - Nov 29
found 8 hours ago
Roundtrip flight included
Washington (DCA) to Chicago (ORD)
Country Inn & Suites by Radisson, Schaumburg, IL

Country Inn & Suites by Radisson, Schaumburg, IL

3 out of 5
Price was $833, price is now $762 per person
$762
per person
Nov 24 - Nov 29
found 8 hours ago
Roundtrip flight included
Washington (DCA) 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 $1,343, price is now $994 per person
$994
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Price was $1,118, price is now $875 per person
$875
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Price was $1,372, price is now $1,109 per person
$1,109
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile

4.5 out of 5
Price was $1,111, price is now $902 per person
$902
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4 out of 5
Price was $1,030, price is now $847 per person
$847
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG

3.5 out of 5
Price was $815, price is now $684 per person
$684
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)

Top places to visit in Cook County

A wooden boardwalk over a river, surrounded by trees and greenery.
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, Jan 4 - Mon, Jan 11
LAX
Los Angeles
ORD
Chicago
$158 Roundtrip, found 1 day ago
$158
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Jan 4 from Los Angeles to Chicago, returning Mon, Jan 11, priced at $158 found 1 day ago
Sat, Feb 27 - Mon, Mar 1
LAX
Los Angeles
ORD
Chicago
$164 Roundtrip, found 15 hours ago
$164
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Sat, Feb 27 from Los Angeles to Chicago, returning Mon, Mar 1, priced at $164 found 15 hours ago
Sun, Nov 15 - Wed, Nov 18
LAX
Los Angeles
MDW
Chicago
$207 Roundtrip, found 5 days ago
$207
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sun, Nov 15 from Los Angeles to Chicago, returning Wed, Nov 18, priced at $207 found 5 days 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
$129 nightly
The price is $153 total per night
$153 total
Nov 10 - Nov 11
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
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
11.01 mi from city center
$152 nightly
The price is $181 total per night
$181 total
Nov 1 - Nov 2
Total with taxes and fees
A stay at River Hotel places you in the heart of Chicago, steps from Michigan Avenue and Chicago Riverwalk.
Pet friendly
Free WiFi
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
11.58 mi from city center
$142 nightly
The price is $169 total per night
$169 total
Nov 1 - Nov 2
Total with taxes and fees
With a stay at The Chicago Hotel Collection - Magnificent Mile in Chicago (Downtown Chicago), you'll be steps from Ann and Robert H. Lurie Children's Hospital and 5 minutes by foot from Museum of Contemporary Art Chicago.
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.