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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.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Save 100% on your flight
Price was $775, price is now $502 per person
$502
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3.5-star boutique hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Save 100% on your flight
Price was $1,031, price is now $663 per person
$663
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, room service, 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.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Save 100% on your flight
Price was $2,210, price is now $1,427 per person
$1,427
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,024, price is now $664 per person
$664
per person
Nov 28 - Dec 3
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $2,035, price is now $1,326 per person
$1,326
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 5-star 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.
Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

3 out of 5
Save 100% on your flight
Price was $801, price is now $527 per person
$527
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Grant Park and Soldier Field 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 $1,165, price is now $771 per person
$771
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3.5-star 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.
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Save 100% on your flight
Price was $1,139, price is now $763 per person
$763
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

Chesterton Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $529, price is now $360 per person
$360
per person
Nov 1 - Nov 4
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 $1,236, price is now $800 per person
$800
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,868, price is now $1,323 per person
$1,323
per person
Oct 21 - Oct 25
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $528, price is now $381 per person
$381
per person
Nov 1 - Nov 4
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 Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,025, price is now $572 per person
$572
per person
Nov 21 - Nov 28
found 19 hours ago
Roundtrip non-stop 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 $1,170, price is now $671 per person
$671
per person
Nov 21 - Nov 28
found 19 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 $1,084, price is now $674 per person
$674
per person
Nov 21 - Nov 28
found 19 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,211, price is now $759 per person
$759
per person
Nov 21 - Nov 28
found 19 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)

Top Flight Deals

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

Spirit Airlines
Tue, Sep 30 - Wed, Oct 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$172 Roundtrip, found 4 days ago
$172
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Tue, Sep 30 from Los Angeles Intl. to O'Hare Intl., returning Wed, Oct 1, priced at $172 found 4 days ago
Frontier Airlines
Thu, Oct 16 - Mon, Oct 20
LAX
Los Angeles Intl.
MDW
Midway Intl.
$178 Roundtrip, found 1 day ago
$178
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Oct 16 from Los Angeles Intl. to Midway Intl., returning Mon, Oct 20, priced at $178 found 1 day ago
EVA Airways
Mon, Sep 22 - Sat, Oct 4
HKG
Hong Kong Intl.
ORD
O'Hare Intl.
$856 Roundtrip, found 10 hours ago
$856
Roundtrip
found 10 hours ago
Select EVA Airways flight, departing Mon, Sep 22 from Hong Kong Intl. to O'Hare Intl., returning Sat, Oct 4, priced at $856 found 10 hours ago
All Nippon Airways
Wed, Nov 5 - Mon, Nov 24
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,000 Roundtrip, found 14 hours ago
$1,000
Roundtrip
found 14 hours ago
Select All Nippon Airways flight, departing Wed, Nov 5 from Pudong Intl. to O'Hare Intl., returning Mon, Nov 24, priced at $1,000 found 14 hours ago