Esmond Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Esmond Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
per person
Oct 1 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Johannesburg (JNB) to Chicago (ORD)
Stay at this 4-star 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
Oct 1 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Johannesburg (JNB) to Chicago (ORD)
Stay at this 5-star 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.
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
per person
Oct 1 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Johannesburg (JNB) to Chicago (ORD)
Stay at this 4-star boutique hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Pendry Chicago
Downtown Chicago
per person
Oct 1 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Johannesburg (JNB) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
per person
Oct 1 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Johannesburg (JNB) to Chicago (ORD)
Stay at this 4-star 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.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
per person
Oct 1 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Johannesburg (JNB) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Top Hotel Deals
Baymont by Wyndham Rockford
662 N Lyford Rd, Rockford, IL
26.76 km from city center
Stay at this 3-star business-friendly hotel in Rockford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Econo Lodge
7712 Potawatomi Trail, Rockford, IL
26.63 km from city center
Stay at this hotel in Rockford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Sleep Inn Rockford I-90
725 Clark Drive, Rockford, IL
26.93 km from city center
Book a stay at this business-friendly hotel in Rockford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the overall ...
Days Inn by Wyndham Rockford I-90 Casino District
220 S Lyford Rd, Rockford, IL
26.4 km from city center
Book a stay at this business-friendly hotel in Rockford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
La Quinta Inn & Suites by Wyndham Rockford
7401 Walton St, Rockford, IL
26.33 km from city center
Stay at this 3-star business-friendly hotel in Rockford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Country Inn & Suites by Radisson, Sycamore, IL
1450 South Peace Road, Sycamore, IL
19.72 km from city center
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. ...
Embassy Suites by Hilton Rockford Riverfront
416 S Main Street, Rockford, IL
29.22 km from city center
Stay at this 3.5-star business-friendly hotel in Rockford. Enjoy free breakfast, 2 restaurants, and 2 bars/lounges. Our guests praise the breakfast and the helpful ...
Holiday Inn Rockford by IHG
7550 E State Street, Rockford, IL
26.62 km from city center
Stay at this 3-star business-friendly hotel in Rockford. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Best Western Sycamore Inn
1935 Dekalb Ave, Sycamore, IL
19.34 km from city center
Book a stay at this business-friendly hotel in Sycamore. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the clean rooms in our reviews. ...
Radisson Hotel and Conference Center Rockford
200 South Bell School Road, Rockford, IL
26.31 km from city center
Stay at this 3-star business-friendly hotel in Rockford. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Hampton Inn DeKalb, IL
663 S. Annie Glidden Road, DeKalb, IL
18.2 km from city center
Stay at this 3-star business-friendly hotel in DeKalb. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Hotel Weston RFD
3909 11th St, Rockford, IL
23.32 km from city center
Stay at this hotel in Rockford. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Don Schmid Park and Sarbrook Park are located ...
Courtyard by Marriott Rockford
7676 E State St, Rockford, IL
26.49 km from city center
Stay at this 3-star business-friendly hotel in Rockford. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
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.
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