Sawyer Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Sawyer Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,695, price is now $1,062 per person
$1,062
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was $1,974, price is now $1,161 per person
$1,161
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Stay at this 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,502, price is now $1,608 per person
$1,608
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
The hotel is beautiful. It has an amazing breakfast buffet, an amazing terrace with great drinks. The staff is super helpful and friendly. This hotel is a 10/10 for sure!
Reviewed on Aug 5, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,873, price is now $1,229 per person
$1,229
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,908, price is now $1,305 per person
$1,305
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
Everything was great.
Reviewed on Aug 4, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,749, price is now $1,224 per person
$1,224
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
N/A
Reviewed on Aug 5, 2026
Top Hotel Deals
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. ...
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 ...
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 ...
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
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
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 ...
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 ...
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 ...
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 ...
Red Roof Inn Benton Harbor - St Joseph
1630 Mall Dr Benton Harbor MI
25.69 km from city center
Stay at this hotel in Benton Harbor. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Silver Beach and Box Factory for the Arts are ...
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 ...
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 ...
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 ...
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.
Sat, Sep 5 - Sun, Sep 6
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$178 Roundtrip, found 2 days ago
$178
Roundtrip
found 2 days ago
Sun, Sep 13 - Sat, Sep 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Wed, Sep 16 - Sun, Sep 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$247 Roundtrip, found 1 day ago
$247
Roundtrip
found 1 day ago
Wed, Sep 16 - Sun, Sep 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$247 Roundtrip, found 1 day ago
$247
Roundtrip
found 1 day ago
Wed, Sep 16 - Sun, Sep 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$346 Roundtrip, found 1 day ago
$346
Roundtrip
found 1 day ago