Cheap Vacations in Northwest Chicago

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3-night Northwest Chicago vacations

Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
per person
May 24 - May 27
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Save 100% on your flight
per person
May 24 - May 27
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
per person
May 24 - May 27
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Wingate by Wyndham - Joliet

Wingate by Wyndham - Joliet

2.5 out of 5
Save 100% on your flight
per person
May 23 - May 26
Roundtrip flight included
Miami (MIA) to Chicago (CHI)
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Save 100% on your flight
per person
May 24 - May 27
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Save 100% on your flight
per person
May 24 - May 27
Roundtrip flight included
Fort Lauderdale (FLL) 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
per person
May 24 - May 27
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Save 100% on your flight
per person
May 24 - May 27
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
per person
May 24 - May 27
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
per person
May 24 - May 27
Roundtrip flight included
Fort Lauderdale (FLL) 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
per person
May 24 - May 27
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Ramada by Wyndham Glendale Heights/Lombard

Ramada by Wyndham Glendale Heights/Lombard

2.5 out of 5
per person
May 23 - May 26
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Prices and availability subject to change. Additional terms may apply.

4-night Northwest Chicago vacations

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Save 100% on your flight
per person
May 28 - Jun 1
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
per person
May 28 - Jun 1
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
per person
May 28 - Jun 1
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
per person
May 28 - Jun 1
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
per person
Jun 1 - Jun 5
Roundtrip non-stop flight included
Ontario (ONT) to Chicago (ORD)
Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop

3 out of 5
Save 100% on your flight
per person
May 28 - Jun 1
Roundtrip flight included
Fort Lauderdale (FLL) 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
per person
May 23 - May 27
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Save 100% on your flight
per person
May 28 - Jun 1
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
The Glen Club

The Glen Club

3.5 out of 5
per person
Jun 1 - Jun 5
Roundtrip non-stop flight included
Ontario (ONT) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
per person
May 28 - Jun 1
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
voco Chicago Downtown, an IHG Hotel

voco Chicago Downtown, an IHG Hotel

3.5 out of 5
Save 100% on your flight
per person
May 28 - Jun 1
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
per person
May 23 - May 27
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Prices and availability subject to change. Additional terms may apply.

5-night Northwest Chicago vacations

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Save 100% on your flight
per person
May 23 - May 28
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Save 100% on your flight
per person
Jun 13 - Jun 18
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
per person
May 23 - May 28
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
per person
May 23 - May 28
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
per person
May 23 - May 28
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Hotel Arista

Hotel Arista

4.5 out of 5
Save 100% on your flight
per person
May 30 - Jun 4
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Bluegreen Vacations Hotel Blake, Ascend Resort Collection

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

3.5 out of 5
Save 100% on your flight
per person
Jun 8 - Jun 13
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
InterContinental Chicago Magnificent Mile, an IHG Hotel

InterContinental Chicago Magnificent Mile, an IHG Hotel

4.5 out of 5
Save 100% on your flight
per person
May 23 - May 28
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
per person
May 30 - Jun 4
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
Save 100% on your flight
per person
May 23 - May 28
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Save 100% on your flight
per person
May 23 - May 28
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Hampton Inn by Hilton Chicago-Midway Airport

Hampton Inn by Hilton Chicago-Midway Airport

2.5 out of 5
Save 100% on your flight
per person
May 30 - Jun 4
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Prices and availability subject to change. Additional terms may apply.

Flight deals to Northwest Chicago

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

Sat, Jun 8 - Tue, Jun 11
LAX
Los Angeles
ORD
Chicago
$126 Roundtrip, found 1 day ago
$126
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, Jun 8 from Los Angeles to Chicago, returning Tue, Jun 11, priced at $126 found 1 day ago
Sat, May 4 - Mon, May 13
LAX
Los Angeles
MDW
Chicago
$128 Roundtrip, found 8 hours ago
$128
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sat, May 4 from Los Angeles to Chicago, returning Mon, May 13, priced at $128 found 8 hours ago
Tue, May 14 - Sat, May 18
LAX
Los Angeles
ORD
Chicago
$128 Roundtrip, found 21 hours ago
$128
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Tue, May 14 from Los Angeles to Chicago, returning Sat, May 18, priced at $128 found 21 hours ago

Top rated hotels for your Northwest Chicago vacation

Eaglewood Resort and Spa

Eaglewood Resort and Spa

4 out of 5
1401 Nordic Rd, Itasca, IL
Free Cancellation
Reserve now, pay when you stay
7.96 mi from city center
The price is $116 per night
$116
per night
Apr 21 - Apr 22
When you stay at Eaglewood Resort and Spa in Itasca, you'll be near the airport, within a 5-minute drive of Bloomingdale Park District Museum and The Oasis Water Park.
Hot Tub
Pool
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
13.51 mi from city center
The price is $185 per night
$185
per night
May 11 - May 12
With a stay at Hilton Chicago O'Hare Airport in Chicago (O'Hare), you'll be within a 10-minute drive of Donald E. Stephens Convention Center and Allstate Arena.
Pet friendly
Breakfast available
Best Western At O'Hare

Best Western At O'Hare

2.5 out of 5
10300 W Higgins Road, Rosemont, IL
Free Cancellation
Reserve now, pay when you stay
14.08 mi from city center
The price is $78 per night
$78
per night
Apr 25 - Apr 26
Located in Rosemont (O'Hare), Best Western At O'Hare is within a 5-minute drive of Allstate Arena and Rivers Casino.
Breakfast included
Parking available
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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.