Search Deals onManhattan Vacation Packages
Manhattan Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Staybridge Suites Chicago O'Hare - Rosemont by IHG
Save 100% on your flight
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Rosemont. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Allstate Arena and Wolff's Flea Market are located nearby.


Holiday Inn Chicago O'Hare – Rosemont by IHG
Save 100% on your flight
per person
Jul 30 - Aug 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Allstate Arena and Wolff's Flea Market are located nearby.

theWit Chicago, a Hilton Hotel
Save 100% on your flight
per person
Jul 30 - Aug 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, 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.

Kimpton Gray Hotel by IHG
Save 100% on your flight
per person
Jul 3 - Jul 6
found 2 days ago
Roundtrip flight included
Boston (BOS) 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 Art Institute of Chicago are located nearby.

Level Chicago - River North
Save 100% on your flight
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Hilton Orrington / Evanston
Save 100% on your flight
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Evanston. 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 Clark Street Beach and Halim Time & Glass Museum are located nearby.

The Hoxton Chicago
Save 100% on your flight
per person
Jul 30 - Aug 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star eco-certified hotel in Chicago. Enjoy free WiFi, an outdoor pool, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Chicago Riverwalk and United Center are located nearby.
Manhattan Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Manhattan Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.



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

Sat, Jul 26 - Sat, Aug 2
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$107 Roundtrip, found 2 days ago
$107
Roundtrip
found 2 days ago

Tue, Jul 1 - Sat, Jul 5
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$182 Roundtrip, found 1 day ago
$182
Roundtrip
found 1 day ago

Fri, Aug 29 - Sat, Aug 30
MCO
Orlando Intl.
MDW
Midway Intl.
$184 Roundtrip, found 4 hours ago
$184
Roundtrip
found 4 hours ago

Tue, Jun 17 - Tue, Jun 17
FLL
Fort Lauderdale - Hollywood Intl.
MDW
Midway Intl.
$205 Roundtrip, found 2 hours ago
$205
Roundtrip
found 2 hours ago
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