Book Exclusive Steward Vacation Packages

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Steward flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was CA $1,227, price is now CA $687 per person
CA $687
per person
Jan 31 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,289, price is now CA $707 per person
CA $707
per person
Jan 31 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $3,192, price is now CA $1,902 per person
CA $1,902
per person
Jan 31 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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 property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,576, price is now CA $1,543 per person
CA $1,543
per person
Jan 31 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,378, price is now CA $841 per person
CA $841
per person
Jan 31 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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.

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
The price is CA $157 per night
CA $157
CA $178 total
Jan 15 - Jan 16, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in DeKalb. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions River Heights Golf Course and Huskie Stadium are located nearby.
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
The price is CA $179 per night
CA $179
CA $204 total
Dec 23 - Dec 24
includes taxes & fees
Book a stay at this business-friendly hotel in DeKalb. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions River Heights Golf Course and Huskie Stadium are located nearby.
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
The price is CA $126 per night
CA $126
CA $140 total
Jan 6 - Jan 7, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Sycamore. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Kiwanis Park and Sycamore Public Library are located nearby.
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
The price is CA $98 per night
CA $98
CA $111 total
Dec 18 - Dec 19
includes taxes & fees
Book a stay at this business-friendly hotel in DeKalb. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Huskie Stadium and NIU Convocation Center are located nearby.
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
The price is CA $83 per night
CA $83
CA $92 total
Jan 6 - Jan 7, 2026
includes taxes & fees
Stay at this motel in Rochelle. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rochelle Railroad Park and Chicagoland Skydiving Center are located nearby.
Motel 6 Sycamore, IL

Motel 6 Sycamore, IL

2 out of 5
1860 Dekalb Ave Sycamore IL
Free cancellation
Reserve now, pay when you stay
The price is CA $75 per night
CA $75
CA $83 total
Dec 28 - Dec 29
includes taxes & fees
Stay at this motel in Sycamore. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Oakland Park and P. A. Nehring Forest Preserve are located nearby.
Pet-friendly
Parking 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.

Steward Vacations

It's always a wise idea to know a thing or two about your destination before you fly off on your escape. Circle Steward on your map now and start packing your bags for an unforgettable adventure!

If you travel 9 miles (14 kilometers) south of Rochelle, or 16 miles (26 kilometers) southwest of DeKalb, you'll arrive in Steward.

It won't be too hard to make new acquaintances in this corner of Illinois. It's home to around around 300 locals.

Hotels in Steward

If you're planning a trip to Steward, keep in mind that there is a limited number of places to stay. Fortunately, Rochelle is just 9 miles (14 kilometers) away and is home to the Holiday Inn Express Rochelle. But be quick — it's the only option on offer!

Places to visit in Steward

Feel like heading into the great outdoors? The countryside at Shabbona Lake State Park is a wonderful place to hurl a ball around or simply sit back and unwind. Want some more ideas? Rochelle Railroad Park is just the ticket for train lovers. Walk around its fabulous exhibits and witness the rich history of the railroad industry come to life.

Where do you fly into for Steward?

Coming in to land at Greater Rockford Airport (RFD)? Once you step off the plane, the middle of Steward is approximately 30 miles (48 kilometers) south away. Slide into a cab and enjoy the journey — your adventure is just beginning!

Frequently asked questions

How much are vacation packages to Steward?
Starting as low as CA $687, 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 113 kilometers from Steward.
Which airport is best for Steward?
O'Hare Intl. Airport (ORD) is popular. You'll find it approximately 97 kilometers east of Steward. Other options worth checking out are Rockford, IL (RFD-Greater Rockford) (40 kilometers away from central Steward) and Lewis University Airport (LOT) (80 kilometers away from central Steward).

Photos of local treasures

Browse Steward vacation photos for more inspiration