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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.
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Save 100% on your flight
Price was $698, price is now $497 per person
$497
per person
Aug 28 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,000, price is now $636 per person
$636
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms 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 $1,074, price is now $699 per person
$699
per person
Sep 3 - Sep 6
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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,216, price is now $797 per person
$797
per person
Sep 13 - Sep 16
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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,374, price is now $914 per person
$914
per person
Jul 31 - Aug 2
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.
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 $1,524, price is now $1,016 per person
$1,016
per person
Aug 27 - Aug 30
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, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $957, price is now $683 per person
$683
per person
Aug 20 - Aug 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.
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
Save 100% on your flight
Price was $905, price is now $646 per person
$646
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this family-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue 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 Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,000, price is now $636 per person
$636
per person
Aug 27 - Aug 30
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 $1,236, price is now $796 per person
$796
per person
Aug 27 - Aug 30
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 $1,074, price is now $699 per person
$699
per person
Sep 3 - Sep 6
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 $1,216, price is now $797 per person
$797
per person
Sep 13 - Sep 16
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 Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,043, price is now $621 per person
$621
per person
Sep 3 - Sep 8
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was $1,583, price is now $869 per person
$869
per person
Sep 3 - Sep 8
found 22 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,843, price is now $1,105 per person
$1,105
per person
Aug 20 - Aug 25
found 24 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was $2,582, price is now $1,626 per person
$1,626
per person
Sep 3 - Sep 8
found 22 hours ago
Roundtrip 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
Sat, Aug 15 - Sat, Aug 29
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$202 Roundtrip, just found
$202
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Aug 15 from Los Angeles Intl. to O'Hare Intl., returning Sat, Aug 29, priced at $202 just found
Frontier Airlines
Tue, Aug 18 - Sat, Sep 12
LAX
Los Angeles Intl.
MDW
Midway Intl.
$269 Roundtrip, found 6 hours ago
$269
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Tue, Aug 18 from Los Angeles Intl. to Midway Intl., returning Sat, Sep 12, priced at $269 found 6 hours ago
American Airlines
Sat, Jul 18 - Sat, Jul 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$419 Roundtrip, found 1 day ago
$419
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Jul 18 from Los Angeles Intl. to Greater Rockford, returning Sat, Jul 25, priced at $419 found 1 day ago
Icelandair
Sat, Jul 4 - Sat, Jul 18
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$728 Roundtrip, found 2 days ago
$728
Roundtrip
found 2 days ago
Select Icelandair flight, departing Sat, Jul 4 from Fiumicino - Leonardo da Vinci Intl. to O'Hare Intl., returning Sat, Jul 18, priced at $728 found 2 days ago