Vacations Close To Outset

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Outset Flight + Hotel packages

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
Price was $665, price is now $530 per person
$530
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)
Roman everything was clean everything was made that was all and it was very

Reviewed on Nov 4, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,033, price is now $731 per person
$731
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)
1

Reviewed on Nov 4, 2026

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $974, price is now $703 per person
$703
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was $833, price is now $650 per person
$650
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)
Breakfast was good

Reviewed on Nov 4, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was $727, price is now $572 per person
$572
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was $822, price is now $676 per person
$676
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)
This is my 3rd time staying at Eurostars and it was excellent as it always has been! Clean rooms, I appreciate the overnight valet, and it is in a great/safe location.

Reviewed on Nov 4, 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was $861, price is now $715 per person
$715
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was $786, price is now $653 per person
$653
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)

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Best Lodging Options Near Outset

STAY

STAY

2 out of 5
1415 Ashland Ave Chicago IL
0.66 km from Outset
Book a stay at this business-friendly hostel in Chicago. Enjoy free WiFi, parking (surcharge), and a 24-hour business center. Our guests praise the helpful staff ...
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
2.99 km from Outset
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
Hyatt Place Chicago/Wicker Park

Hyatt Place Chicago/Wicker Park

3 out of 5
1551 West North Ave Chicago IL
0.41 km from Outset
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Our guests praise the breakfast and the bar in our ...
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
5.27 km from Outset
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
The Robey, Chicago, a Member of Design Hotels

The Robey, Chicago, a Member of Design Hotels

3.5 out of 5
2018 W. North Ave. Chicago IL
1.25 km from Outset
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and 3 bars/lounges. Our guests praise the helpful staff in our reviews. ...
Wicker Park Inn

Wicker Park Inn

3.5 out of 5
1331 N Wicker Park Ave Chicago IL
1.04 km from Outset
Book a stay at this business-friendly B&B in Chicago. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the helpful staff in our reviews. ...
ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments

2 out of 5
853 W Blackhawk St Chicago IL
1.18 km from Outset
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Michigan Avenue and Chicago Riverwalk ...
ENVITAE Hotel

ENVITAE Hotel

2 out of 5
853 W Blackhawk St Chicago IL
1.18 km from Outset
Stay at this hotel in Chicago. Enjoy free WiFi, premium bedding, and in-room washers/dryers. Popular attractions Michigan Avenue and Chicago Riverwalk are located ...
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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.