Search Deals on
Manhattan Vacation Packages

Build your package with 2 more options

Manhattan Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $772, price is now $463 per person
$463
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Amazing. Book here always.

Reviewed on Sep 10, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Save 100% on your flight
Price was $1,180, price is now $685 per person
$685
per person
Nov 23 - Nov 30
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 a 24-hour 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.
Old,

Reviewed on Sep 8, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,464, price is now $917 per person
$917
per person
Oct 15 - Oct 19
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.
The pool & jacuzzi was perfect, this hotel is beautiful

Reviewed on Sep 7, 2026

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 $781, price is now $491 per person
$491
per person
Oct 29 - Nov 1
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.

The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $742, price is now $478 per person
$478
per person
Oct 29 - Nov 1
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.

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,502, price is now $1,007 per person
$1,007
per person
Nov 28 - Dec 4
just found
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.
Location and facility was very nice

Reviewed on Sep 7, 2026

Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $815, price is now $551 per person
$551
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Good location

Reviewed on Sep 6, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,843, price is now $1,249 per person
$1,249
per person
Nov 28 - Dec 4
just found
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.

Manhattan Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $777, price is now $456 per person
$456
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,028, price is now $545 per person
$545
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $797, price is now $492 per person
$492
per person
Oct 29 - Nov 1
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 $1,464, price is now $917 per person
$917
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Manhattan Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,180, price is now $685 per person
$685
per person
Nov 23 - Nov 30
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 $1,571, price is now $855 per person
$855
per person
Nov 23 - Nov 30
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 $2,080, price is now $1,229 per person
$1,229
per person
Nov 24 - Nov 29
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,598, price is now $1,004 per person
$1,004
per person
Nov 28 - Dec 4
found 6 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
Tue, Nov 17 - Thu, Nov 19
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$94 Roundtrip, found 12 hours ago
$94
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Tue, Nov 17 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Thu, Nov 19, priced at $94 found 12 hours ago
Frontier Airlines
Sat, Nov 7 - Tue, Nov 17
FLL
Fort Lauderdale - Hollywood Intl.
MDW
Midway Intl.
$191 Roundtrip, found 16 hours ago
$191
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Sat, Nov 7 from Fort Lauderdale - Hollywood Intl. to Midway Intl., returning Tue, Nov 17, priced at $191 found 16 hours ago
Frontier Airlines
Tue, Oct 6 - Sat, Oct 10
DEN
Denver Intl.
MDW
Midway Intl.
$203 Roundtrip, found 18 hours ago
$203
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Tue, Oct 6 from Denver Intl. to Midway Intl., returning Sat, Oct 10, priced at $203 found 18 hours ago
Frontier Airlines
Wed, Oct 21 - Sat, Oct 24
MCO
Orlando Intl.
MDW
Midway Intl.
$220 Roundtrip, found 6 days ago
$220
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Oct 21 from Orlando Intl. to Midway Intl., returning Sat, Oct 24, priced at $220 found 6 days ago