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Northwest Indiana Vacation Packages

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Northwest Indiana Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Dorothy's

Dorothy's

2 out of 5
Save 100% on your flight
Price was $377, price is now $266 per person
$266
per person
Dec 15 - Dec 19
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this B&B in Chicago. Enjoy free breakfast, free WiFi, and housekeeping. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
Dorothy's is a nice place for people wanting easy access to a clean, SRO-style room in a good location with an invisible staff (online checkin). Specific complaints: my room lacked both trash can and bedside light. And the self-serve breakfast provided nice individual portions of yogurt and bags of nuts, but on neither morning was coffee available (happily there are places only blocks away to buy some). Plus, charging extra for checking in 1-3-hours earlier than the 4pm check-in seems a little tacky (I've been traveling for many decades and never confronted this add-on).

Reviewed on Oct 12, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $739, price is now $461 per person
$461
per person
Dec 8 - Dec 12
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 a fitness center. 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 $1,217, price is now $761 per person
$761
per person
Dec 31 - Jan 5
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.
The stay was all good as represented on the site!

Reviewed on Oct 12, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $670, price is now $461 per person
$461
per person
Dec 23 - Dec 27
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.
The staff is super nice and great amenities

Reviewed on Oct 11, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,150, price is now $796 per person
$796
per person
Dec 18 - Dec 21
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.
Great location

Reviewed on Oct 12, 2026

The Wade

The Wade

4.5 out of 5
Save 100% on your flight
Price was $470, price is now $330 per person
$330
per person
Dec 3 - Dec 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, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.
Great location for those that want to be downtown with easy access to everything!

Reviewed on Oct 13, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $934, price is now $675 per person
$675
per person
Nov 12 - Nov 15
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 Peninsula Chicago

The Peninsula Chicago

5 out of 5
Save 100% on your flight
Price was $2,568, price is now $1,868 per person
$1,868
per person
Dec 20 - Dec 26
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 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Northwest Indiana Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $408, price is now $246 per person
$246
per person
Dec 3 - Dec 6
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 $664, price is now $407 per person
$407
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $739, price is now $461 per person
$461
per person
Dec 8 - Dec 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $571, price is now $367 per person
$367
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Northwest Indiana Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $946, price is now $590 per person
$590
per person
Dec 31 - Jan 5
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 $2,023, price is now $1,152 per person
$1,152
per person
Nov 14 - Nov 21
found 8 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,023, price is now $626 per person
$626
per person
Dec 31 - Jan 5
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 $2,116, price is now $1,325 per person
$1,325
per person
Nov 14 - Nov 21
found 8 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)

Top Flight Deals

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

American Airlines
Thu, Nov 12 - Fri, Nov 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 10 hours ago
$197
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Thu, Nov 12 from Los Angeles Intl. to O'Hare Intl., returning Fri, Nov 13, priced at $197 found 10 hours ago
Southwest Airlines
Wed, Nov 11 - Fri, Nov 13
LAX
Los Angeles Intl.
MDW
Midway Intl.
$197 Roundtrip, found 19 hours ago
$197
Roundtrip
found 19 hours ago
Select Southwest Airlines flight, departing Wed, Nov 11 from Los Angeles Intl. to Midway Intl., returning Fri, Nov 13, priced at $197 found 19 hours ago
United
Wed, Nov 4 - Mon, Nov 9
LAX
Los Angeles Intl.
SBN
South Bend Intl.
$437 Roundtrip, just found
$437
Roundtrip
just found
Select United flight, departing Wed, Nov 4 from Los Angeles Intl. to South Bend Intl., returning Mon, Nov 9, priced at $437 just found
Philippine Airlines
Fri, Nov 13 - Wed, Dec 2
PVG
Pudong Intl.
ORD
O'Hare Intl.
$998 Roundtrip, found 1 day ago
$998
Roundtrip
found 1 day ago
Select Philippine Airlines flight, departing Fri, Nov 13 from Pudong Intl. to O'Hare Intl., returning Wed, Dec 2, priced at $998 found 1 day ago