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Northwest Chicago Vacation Packages

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Northwest Chicago Flight + Hotel Packages

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

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $320, price is now $169 per person
$169
per person
Jan 23 - Jan 25
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Price was $1,440, price is now $520 per person
$520
per person
Dec 23 - Dec 28
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The French Country Inn Lake Geneva

The French Country Inn Lake Geneva

3 out of 5
Save 100% on your flight
Price was $552, price is now $302 per person
$302
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this hotel in Lake Geneva. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Geneva National Golf Club and Lake Como are located nearby.
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $951, price is now $529 per person
$529
per person
Dec 23 - Dec 28
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $478, price is now $270 per person
$270
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Save 100% on your flight
Price was $310, price is now $178 per person
$178
per person
Jan 23 - Jan 25
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $552, price is now $316 per person
$316
per person
Jan 23 - Jan 25
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 out of 5
Save 100% on your flight
Price was $702, price is now $410 per person
$410
per person
Jan 16 - Jan 23
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Northwest Chicago Vacation Packages 3-4 Night Stays

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

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $418, price is now $215 per person
$215
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,249, price is now $597 per person
$597
per person
Dec 23 - Dec 27
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $841, price is now $443 per person
$443
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $406, price is now $221 per person
$221
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Northwest Chicago Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
Downtown Chicago
Price was $704, price is now $358 per person
$358
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,440, price is now $520 per person
$520
per person
Dec 23 - Dec 28
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was $946, price is now $424 per person
$424
per person
Feb 12 - Feb 17
found 16 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,300, price is now $682 per person
$682
per person
Feb 12 - Feb 17
found 16 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)

Top Flight Deals

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

Frontier Airlines
Fri, Dec 12 - Mon, Dec 15
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$93 Roundtrip, found 1 day ago
$93
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Dec 12 from Los Angeles Intl. to O'Hare Intl., returning Mon, Dec 15, priced at $93 found 1 day ago
Frontier Airlines
Mon, Dec 8 - Thu, Dec 11
LAX
Los Angeles Intl.
MDW
Midway Intl.
$196 Roundtrip, found 2 days ago
$196
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Dec 8 from Los Angeles Intl. to Midway Intl., returning Thu, Dec 11, priced at $196 found 2 days ago
Lufthansa
Thu, Dec 4 - Mon, Dec 15
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$700 Roundtrip, found 1 day ago
$700
Roundtrip
found 1 day ago
Select Lufthansa flight, departing Thu, Dec 4 from Fiumicino - Leonardo da Vinci Intl. to O'Hare Intl., returning Mon, Dec 15, priced at $700 found 1 day ago
Delta
Thu, Dec 4 - Tue, Dec 16
FCO
Fiumicino - Leonardo da Vinci Intl.
MDW
Midway Intl.
$738 Roundtrip, found 3 days ago
$738
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Dec 4 from Fiumicino - Leonardo da Vinci Intl. to Midway Intl., returning Tue, Dec 16, priced at $738 found 3 days ago