Vacation Packages to Indiana for 2026
Indiana Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago Dwtn - The Mart by IHG
Downtown Chicago
Save 100% on your flight
Price was $1,702, price is now $1,225 per person
$1,225
per person
Jul 22 - Jul 28
found 5 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, 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.
Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,844, price is now $1,257 per person
$1,257
per person
Jul 22 - Jul 28
found 5 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, 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.
Hilton Garden Inn Chicago Downtown Riverwalk
Downtown Chicago
Save 100% on your flight
Price was $1,965, price is now $1,375 per person
$1,375
per person
Jul 22 - Jul 28
found 5 hours ago
Roundtrip flight included
San Juan (SJU) 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.
Holiday Inn & Suites Chicago - Downtown by IHG
Downtown Chicago
Save 100% on your flight
Price was $1,970, price is now $1,416 per person
$1,416
per person
Jul 22 - Jul 28
found 5 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,720, price is now $1,245 per person
$1,245
per person
Jul 22 - Jul 28
found 5 hours ago
Roundtrip flight included
San Juan (SJU) 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.
Kinzie Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,769, price is now $1,288 per person
$1,288
per person
Jul 22 - Jul 28
found 5 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Top Hotel Deals
Blue Chip Casino Hotel and Spa
777 Blue Chip Drive Michigan City IN
173.52 km from city center
Book a stay at this spa hotel in Michigan City. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff and the clean rooms ...
Ironworks Hotel Indy
2721 E 86th Street Indianapolis IN
39.57 km from city center
Book a stay at this business-friendly hotel in Indianapolis. Enjoy free WiFi, free parking, and 4 restaurants. Our guests praise the helpful staff and the clean ...
Omni Severin Hotel
40 West Jackson Place Indianapolis IN
56.01 km from city center
Book a stay at this business-friendly hotel in Indianapolis. Enjoy breakfast (surcharge), room service, and a 24-hour health club. Our guests praise the helpful ...
The Fontana Hotel
7304 E 21st St Indianapolis IN
52.87 km from city center
Book a stay at this business-friendly hotel in Indianapolis. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff ...
Drury Inn & Suites Lafayette, IN
4110 South Street Lafayette IN
61.07 km from city center
Book a stay at this business-friendly hotel in Lafayette. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Irish Lodge South Bend
52709 Indiana State Route 933 South Bend IN
162.64 km from city center
Book a stay at this business-friendly hotel in South Bend. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Best Western Plus Indianapolis North at Pyramids
9320 N Michigan Rd Indianapolis IN
39.27 km from city center
Book a stay at this business-friendly hotel in Indianapolis. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the ...
Courtyard by Marriott Indianapolis Downtown
601 West Washington Street Indianapolis IN
55.65 km from city center
Book a stay at this business-friendly hotel in Indianapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
Comfort Inn Lafayette I-65
4701 Meijer Court Lafayette IN
60.22 km from city center
Book a stay at this business-friendly hotel in Lafayette. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Baymont by Wyndham Plainfield/ Indianapolis Arpt Area
6010 Gateway Dr Plainfield IN
68.96 km from city center
Book a stay at this business-friendly hotel in Plainfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Sybaris Pool Suites Indianapolis
5466 W.86th Street Indianapolis IN
40.97 km from city center
Stay at this hotel in Indianapolis. Enjoy private hot tubs, a steam room, and a cruise terminal shuttle (surcharge). Popular attractions Zionsville Road Trailhead ...
Best Western Plus Greenwood/Indy South Inn
1281 South Park Drive Greenwood IN
72.64 km from city center
Book a stay at this business-friendly hotel in Greenwood. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
JW Marriott Indianapolis
10 S West Street Indianapolis IN
55.74 km from city center
Book a stay at this business-friendly hotel in Indianapolis. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Wed, Jul 22 - Wed, Jul 29
ATL
Atlanta
IND
Indianapolis
$90 Roundtrip, found 1 hour ago
$90
Roundtrip
found 1 hour ago
Tue, Aug 18 - Tue, Sep 1
EWR
New York
ORD
Chicago
$187 Roundtrip, found 1 day ago
$187
Roundtrip
found 1 day ago
Tue, Sep 29 - Tue, Oct 6
EWR
New York
MDW
Chicago
$223 Roundtrip, found 2 days ago
$223
Roundtrip
found 2 days ago
Tue, Oct 6 - Wed, Oct 14
PHX
Phoenix
MDW
Chicago
$245 Roundtrip, found 1 day ago
$245
Roundtrip
found 1 day ago