
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 $1,059, price is now $817 per person
$817
per person
Dec 21 - Dec 28
found 20 hours ago
Roundtrip flight included
San Diego (SAN) 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 room was not ready upon arrival so we had to wait 45 min after check in to get into our room. Additionally, we left the room at 930a , returned at 6p and the room had not been cleaned. There were fresh towels laid on top of the bed but nothing else had been touched. Seemed a little disorganized bc when we asked why the room had been left untouched they said “they were just really busy bc they were booked” but idk, if I’m paying to stay there, it’s not my job to make sure you can handle the level of occupancy you booked. It’s pretty centrally located but I wouldn’t stay here again
Reviewed on Nov 15, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,606, price is now $1,102 per person
$1,102
per person
Dec 21 - Dec 28
found 20 hours ago
Roundtrip flight included
San Diego (SAN) 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.
Top notch hotel. Never stayed at a Riu property before, but will definitely look into one whenever I am out of town. Clean, modern, and spacious rooms, terrific customer service and the breakfast buffet was very good too.
Reviewed on Nov 15, 2026

Eurostars Magnificent Mile
Downtown Chicago
Price was $1,576, price is now $1,136 per person
$1,136
per person
Dec 21 - Dec 28
found 20 hours ago
Roundtrip flight included
San Diego (SAN) 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.

The Blackstone, Autograph Collection
Downtown Chicago
Price was $1,126, price is now $829 per person
$829
per person
Dec 24 - Dec 31
found 16 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy a 24-hour fitness center, parking (surcharge), and onsite spa services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.

Swissotel - Chicago
Downtown Chicago
Price was $1,323, price is now $1,012 per person
$1,012
per person
Dec 21 - Dec 28
found 20 hours ago
Roundtrip flight included
San Diego (SAN) 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.
Beautiful building Nice room sweet customer services. The no microwave and charging customers to warm their food is honestly insane and inconsiderate. It was a 5/10 probably will not be a returning customer.
Reviewed on Nov 15, 2026

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
Price was $1,080, price is now $829 per person
$829
per person
Dec 21 - Dec 28
found 20 hours ago
Roundtrip flight included
San Diego (SAN) 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.
A
Reviewed on Nov 12, 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. ...

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 ...

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 ...

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 5 - Sat, Jan 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$257 Roundtrip, found 2 days ago
$257
Roundtrip
found 2 days ago

Tue, Feb 23 - Wed, Feb 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$257 Roundtrip, found 17 hours ago
$257
Roundtrip
found 17 hours ago

Tue, Jan 5 - Sat, Jan 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$257 Roundtrip, found 2 days ago
$257
Roundtrip
found 2 days ago

Tue, Jan 26 - Tue, Feb 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$262 Roundtrip, found 4 days ago
$262
Roundtrip
found 4 days ago

Tue, Jan 5 - Sat, Jan 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$274 Roundtrip, found 2 days ago
$274
Roundtrip
found 2 days ago

