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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was $783, price is now $604 per person
$604
per person
Dec 17 - Dec 22
found 1 day ago
Roundtrip flight included
President Donald J. Trump Intl. Airport (DJT) 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.
The bathroom in my room was looking worse for wear, broken tiles and caulk missing.
However the room itself was clean and staff was sooooo helpful and courteous which made my stay great! I even was out of body wash and the girl at the front desk made sure I got some after house keeping didn’t bring any after an hour and I wanted to shower.
Good people working here!
Reviewed on Oct 28, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,183, price is now $736 per person
$736
per person
Dec 17 - Dec 22
found 1 day ago
Roundtrip flight included
President Donald J. Trump Intl. Airport (DJT) 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.
Great location, nice rooms, nice rooftop bar and large breakfast buffet included.
Reviewed on Oct 28, 2026
The Talbott, Autograph Collection
Downtown Chicago
Price was $873, price is now $640 per person
$640
per person
Dec 17 - Dec 22
found 1 day ago
Roundtrip flight included
President Donald J. Trump Intl. Airport (DJT) 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.
Swissotel - Chicago
Downtown Chicago
Price was $889, price is now $666 per person
$666
per person
Dec 17 - Dec 22
found 1 day ago
Roundtrip flight included
President Donald J. Trump Intl. Airport (DJT) 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.
I will come back and recommend
Reviewed on Oct 29, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was $979, price is now $770 per person
$770
per person
Dec 17 - Dec 22
found 1 day ago
Roundtrip flight included
President Donald J. Trump Intl. Airport (DJT) 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.
Great view, calming. Everything is within walking distance. Some confusion from vendor to vendor on what was included. All in all, we would stay again.
Reviewed on Oct 28, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was $925, price is now $728 per person
$728
per person
Dec 17 - Dec 22
found 1 day ago
Roundtrip flight included
President Donald J. Trump Intl. Airport (DJT) 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.
I love hotels with an excellent restaurant. Excellent staff, really kind and professional. I’ll be sure to return on my next trip to CHI
Reviewed on Oct 29, 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. ...
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 ...
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 ...
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
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. ...
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
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 ...
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 ...
Comfort Inn La Porte
100 Eastshore Court La Porte IN
30.92 km from city center
Book a stay at this business-friendly hotel in La Porte. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the breakfast and ...
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 ...
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 ...
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.
Tue, Jan 26 - Wed, Feb 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$150 Roundtrip, found 5 days ago
$150
Roundtrip
found 5 days ago
Tue, Jan 5 - Sat, Jan 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$235 Roundtrip, found 5 days ago
$235
Roundtrip
found 5 days ago
Sat, Nov 21 - Tue, Dec 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$255 Roundtrip, found 6 days ago
$255
Roundtrip
found 6 days ago
Wed, Mar 24 - Mon, Mar 29
LAX
Los Angeles Intl.
MDW
Midway Intl.
$433 Roundtrip, found 4 days ago
$433
Roundtrip
found 4 days ago