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Chesterton Vacation Packages

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Chesterton Flight + Hotel Packages

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

Arlo Chicago

4 out of 5
Save 100% on your flight
Price was $328, price is now $211 per person
$211
per person
Feb 18 - Feb 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Save 100% on your flight
Price was $409, price is now $240 per person
$240
per person
Feb 3 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Zion. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Illinois Beach State Park and Carmel Park are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $390, price is now $234 per person
$234
per person
Feb 18 - Feb 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. 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 $1,016, price is now $615 per person
$615
per person
Mar 5 - Mar 8
found 1 day 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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,002, price is now $620 per person
$620
per person
Feb 10 - Feb 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $633, price is now $396 per person
$396
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $632, price is now $401 per person
$401
per person
Mar 5 - Mar 8
found 1 day 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 Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $724, price is now $479 per person
$479
per person
Mar 20 - Mar 23
found 1 day 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.

Chesterton Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $390, price is now $234 per person
$234
per person
Feb 18 - Feb 21
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 $1,016, price is now $615 per person
$615
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $633, price is now $396 per person
$396
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $632, price is now $401 per person
$401
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Chesterton Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Blackstone, Autograph Collection

The Blackstone, Autograph Collection

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $854, price is now $493 per person
$493
per person
Feb 10 - Feb 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $980, price is now $518 per person
$518
per person
Feb 10 - Feb 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,107, price is now $610 per person
$610
per person
Feb 10 - Feb 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $896, price is now $504 per person
$504
per person
Feb 10 - Feb 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)

Top Flight Deals

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

Frontier Airlines
Tue, Feb 10 - Wed, Feb 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$163 Roundtrip, found 2 hours ago
$163
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, Feb 10 from Los Angeles Intl. to O'Hare Intl., returning Wed, Feb 18, priced at $163 found 2 hours ago
Frontier Airlines
Tue, Jan 13 - Thu, Jan 15
LAX
Los Angeles Intl.
MDW
Midway Intl.
$196 Roundtrip, found 4 days ago
$196
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Jan 13 from Los Angeles Intl. to Midway Intl., returning Thu, Jan 15, priced at $196 found 4 days ago
American Airlines
Fri, Jan 9 - Sun, Jan 11
LAX
Los Angeles Intl.
RFD
Greater Rockford
$347 Roundtrip, found 4 days ago
$347
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Jan 9 from Los Angeles Intl. to Greater Rockford, returning Sun, Jan 11, priced at $347 found 4 days ago
Hong Kong Airlines
Mon, May 11 - Wed, May 27
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,128 Roundtrip, found 8 hours ago
$1,128
Roundtrip
found 8 hours ago
Select Hong Kong Airlines flight, departing Mon, May 11 from Pudong Intl. to O'Hare Intl., returning Wed, May 27, priced at $1,128 found 8 hours ago