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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.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
Price was $281, price is now $159 per person
$159
per person
Jan 9 - Jan 11
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 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Price was $680, price is now $336 per person
$336
per person
Feb 4 - Feb 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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $365, price is now $196 per person
$196
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $587, price is now $316 per person
$316
per person
Feb 13 - Feb 15
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.
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 $420, price is now $231 per person
$231
per person
Feb 4 - Feb 8
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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $546, price is now $303 per person
$303
per person
Feb 20 - Feb 22
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.
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
Save 100% on your flight
Price was $437, price is now $243 per person
$243
per person
Jan 7 - Jan 10
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (MDW)
Book a stay at this spa resort in Hazel Crest. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Midwest Carvers Museum and Ravisloe Country Club are located nearby.
Arlo Chicago

Arlo Chicago

4 out of 5
Save 100% on your flight
Price was $347, price is now $204 per person
$204
per person
Jan 16 - Jan 19
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.

Chesterton Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $504, price is now $259 per person
$259
per person
Jan 16 - Jan 20
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
Price was $680, price is now $336 per person
$336
per person
Feb 4 - Feb 8
found 1 day ago
Roundtrip 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 $761, price is now $404 per person
$404
per person
Feb 20 - Feb 23
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $511, price is now $275 per person
$275
per person
Feb 4 - Feb 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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $525, price is now $270 per person
$270
per person
Jan 14 - Jan 19
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was $799, price is now $401 per person
$401
per person
Jan 16 - Jan 23
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 $615, price is now $311 per person
$311
per person
Jan 14 - Jan 19
found 15 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 $545, price is now $277 per person
$277
per person
Jan 14 - Jan 19
found 15 hours ago
Roundtrip 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.

Frontier Airlines
Thu, Dec 25 - Mon, Jan 12
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$140 Roundtrip, found 5 days ago
$140
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Dec 25 from Los Angeles Intl. to O'Hare Intl., returning Mon, Jan 12, priced at $140 found 5 days ago
Delta
Thu, Jan 8 - Mon, Jan 12
LAX
Los Angeles Intl.
MDW
Midway Intl.
$208 Roundtrip, found 22 hours ago
$208
Roundtrip
found 22 hours ago
Select Delta flight, departing Thu, Jan 8 from Los Angeles Intl. to Midway Intl., returning Mon, Jan 12, priced at $208 found 22 hours ago
American Airlines
Fri, Jan 9 - Sun, Jan 11
LAX
Los Angeles Intl.
RFD
Greater Rockford
$359 Roundtrip, found 1 day ago
$359
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Jan 9 from Los Angeles Intl. to Greater Rockford, returning Sun, Jan 11, priced at $359 found 1 day ago
American Airlines
Sat, Dec 6 - Tue, Dec 9
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$656 Roundtrip, found 6 days ago
$656
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Dec 6 from Fiumicino - Leonardo da Vinci Intl. to O'Hare Intl., returning Tue, Dec 9, priced at $656 found 6 days ago