Deals on vacations and trips to Steward

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Steward flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Delta Hotels by Marriott Chicago Willowbrook

Delta Hotels by Marriott Chicago Willowbrook

3 out of 5
Price was $503, price is now $372 per person
$372
per person
Feb 19 - Feb 24
found 5 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a grocery/convenience store, and a computer station are also offered.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was $1,516, price is now $1,058 per person
$1,058
per person
Feb 19 - Feb 24
found 5 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $847, price is now $602 per person
$602
per person
Mar 12 - Mar 17
found 12 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and a coffee shop are also provided.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $793, price is now $582 per person
$582
per person
Mar 12 - Mar 17
found 12 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a coffee shop, and a snack bar/deli are also offered.
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Price was $1,207, price is now $890 per person
$890
per person
Feb 19 - Feb 24
found 5 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. A coffee shop, express check-out, and dry cleaning are also on offer.

Top Steward hotels deals

Hampton Inn DeKalb, IL

Hampton Inn DeKalb, IL

3 out of 5
663 S. Annie Glidden Road DeKalb IL
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $129 total per night
$129 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, express check-in, and express check-out are also offered.
Pool
Breakfast included
Country Inn & Suites by Radisson, Sycamore, IL

Country Inn & Suites by Radisson, Sycamore, IL

2.5 out of 5
1450 South Peace Road Sycamore IL
Free Cancellation
$92 nightly
The price is $102 total per night
$102 total
Jan 26 - Jan 27, 2026
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
Pool
Breakfast included
Home2 Suites by Hilton Dekalb

Home2 Suites by Hilton Dekalb

3 out of 5
575 S ANNIE GLIDDEN RD DeKalb IL
Free Cancellation
Reserve now, pay when you stay
$130 nightly
The price is $148 total per night
$148 total
Jan 16 - Jan 17, 2026
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Comfort Inn DeKalb - University Area

Comfort Inn DeKalb - University Area

2.5 out of 5
W Lincoln Hwy, 1314,1314 DeKalb IL
Free Cancellation
Reserve now, pay when you stay
$71 nightly
The price is $81 total per night
$81 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. Enjoy the gym and conveniences like a 24-hour front desk and free newspapers.
Breakfast included
Pet friendly
Super 8 by Wyndham Rochelle

Super 8 by Wyndham Rochelle

2 out of 5
601 E Highway 38 Rochelle IL
Free Cancellation
Reserve now, pay when you stay
$58 nightly
The price is $65 total per night
$65 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
This motel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free on-the-go breakfast each morning. The front desk is staffed around-the-clock and free newspapers are on offer.
Breakfast included
Parking included
Quality Inn

Quality Inn

2.5 out of 5
567 E IL Route 38 Rochelle IL
Free Cancellation
Reserve now, pay when you stay
$63 nightly
The price is $70 total per night
$70 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
A casino and an outdoor pool are featured at this smoke-free hotel. Enjoy the gym and free perks like continental breakfast and free self parking. A business center, free WiFi in public areas, and laundry facilities are also on offer.
Pool
Breakfast included
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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.

Frequently asked questions

How much are vacation packages to Steward?
Starting as low as $372, hotel and flight packages are a great way to stretch your travel budget. Get ready Steward — here you come!
Where can I get the best vacation package deals for Steward?
Travelocity is the only place you need to go to score an amazing Steward package deal. Choose from 400 air carriers and 1,000,000 properties worldwide and put together a travel itinerary that's right for you. With so many options at hand, it's easy to organize your next great adventure.
Why should I purchase my Steward vacation bundle via Travelocity?
We offer 24/7 support, top-notch service and a Price Match Guarantee. Life is one big journey — and we have amazing destinations for you to journey to all over the world. Travel with us and make your hip pocket happy.
Can I save money on my Steward car rental if I bundle it with my hotel or flight?
Sure can — bundle your hotel, car and flight into a Steward vacation package and you'll save a tidy sum. With so many places to explore in the Steward area, that set of wheels will make exploring a breeze. Once you've buckled yourself in, turn up the stereo and head to Wrigley Field, a well-known sight approximately 70 mi from Steward.
Which airport is best for Steward?
O'Hare Intl. Airport (ORD) is popular. You'll find it approximately 60 mi east of Steward. Other options worth checking out are Rockford, IL (RFD-Greater Rockford) (25 mi away from central Steward) and Lewis University Airport (LOT) (50 mi away from central Steward).

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