Sawyer Vacations

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Sawyer 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

Downtown Chicago
$514
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
The staff was 10/10.

Reviewed on Oct 15, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$751
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) 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.
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
$640
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
$565
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) 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.
Holiday Inn Express Chicago - Magnificent Mile by IHG

Holiday Inn Express Chicago - Magnificent Mile by IHG

Downtown Chicago
$563
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Downtown Chicago
$703
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) 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.
Property is not easily accessible by persons with limited mobility.

Reviewed on Oct 16, 2026

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Top Hotel Deals

Quality Inn Sawyer

Quality Inn Sawyer

12850 Super Dr Sawyer MI
0.66 km from city center
Stay at this hotel in Sawyer. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

11111 Wilson Road New Buffalo MI
15.23 km from city center
Book a stay at this business-friendly hotel in New Buffalo. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
Silver Beach Hotel

Silver Beach Hotel

100 Main Street Saint Joseph MI
26.58 km from city center
Book a stay at this business-friendly hotel in Saint Joseph. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

777 Blue Chip Drive Michigan City IN
31.13 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 ...
The Boulevard Inn & Bistro

The Boulevard Inn & Bistro

521 Lake Blvd Saint Joseph MI
26.21 km from city center
Stay at this hotel in Saint Joseph. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular ...
The Inn At Harbor Shores

The Inn At Harbor Shores

800 Whitwam Dr Saint Joseph MI
27.34 km from city center
Book a stay at this spa hotel in Saint Joseph. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in ...
Wingate by Wyndham South Bend/Notre Dame

Wingate by Wyndham South Bend/Notre Dame

52890 State Rt 933 N South Bend IN
33.35 km from city center
Stay at this hotel in South Bend. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. ...
Irish Lodge South Bend

Irish Lodge South Bend

52709 Indiana State Route 933 South Bend IN
33.1 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 ...
Baymont By Wyndham South Bend

Baymont By Wyndham South Bend

215 South Dixie Way South Bend IN
33.96 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 ...
Pine Lake Resort and Banquets

Pine Lake Resort and Banquets

444 Pine Lake Ave La Porte IN
31.8 km from city center
Book a stay at this spa hotel in La Porte. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
La Quinta Suites by Wyndham South Bend Notre Dame Area

La Quinta Suites by Wyndham South Bend Notre Dame Area

52554 STATE ROAD 933 South Bend IN
33.09 km from city center
Book a stay at this business-friendly hotel in South Bend. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the ...
Holiday Inn Express & Suites New Buffalo by IHG

Holiday Inn Express & Suites New Buffalo by IHG

11500 Holiday Dr New Buffalo MI
16.77 km from city center
Stay at this hotel in New Buffalo. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
Baymont by Wyndham New Buffalo

Baymont by Wyndham New Buffalo

18800 Harbor Country Drive New Buffalo MI
16.79 km from city center
Book a stay at this business-friendly hotel in New Buffalo. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the clean rooms ...
Quality Inn Near Interstate I94

Quality Inn Near Interstate I94

18830 Laporte Rd New Buffalo MI
16.87 km from city center
Stay at this hotel in New Buffalo. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Hampton Inn & Suites Benton Harbor

Hampton Inn & Suites Benton Harbor

1921 Pipestone Rd Benton Harbor MI
26.13 km from city center
Book a stay at this business-friendly hotel in Benton Harbor. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the ...
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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.

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.

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