Streeterville Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Top Hotel Deals
Hampton Inn Chicago Downtown/Magnificent Mile
160 E Huron Street Chicago IL
Book a stay at this family-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the ...
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
The Wade
644 N Lake Shore Dr Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
Warwick Allerton - Chicago
701 North Michigan Avenue Chicago IL
Book a stay at this family-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise ...
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
201 East Walton Place Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful ...
Hotel Saint Clair- Magnificent Mile
162 East Ontario Street Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
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 ...
The Whitehall Hotel, BW Premier Collection
105 E Delaware Pl Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the restaurant and the helpful ...
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
511 North Columbus Drive Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful ...
Sable at Navy Pier Chicago, Curio Collection by Hilton
900 E Grand Chicago IL
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 ...
DoubleTree by Hilton Chicago - Magnificent Mile
300 E Ohio St Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy an outdoor pool, a rooftop terrace, and breakfast (surcharge). Our guests praise the pool and the ...
Sheraton Grand Chicago Riverwalk
301 E North Water St Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful ...
Aloft by Marriott Chicago Mag Mile
243 E. Ontario Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool and the helpful staff in our reviews. ...
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, Nov 10 - Thu, Nov 12
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217
Roundtrip
found 1 day ago
Mon, Nov 9 - Sat, Nov 14
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217
Roundtrip
found 1 day ago
Tue, Oct 13 - Tue, Oct 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217
Roundtrip
found 4 days ago
Fri, Oct 2 - Mon, Oct 5
LAX
Los Angeles Intl.
MDW
Midway Intl.
$237
Roundtrip
found 2 days ago
Thu, Oct 1 - Mon, Oct 5
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$264
Roundtrip
found 5 days ago
Best points of interest in Chicago
- Navy Pier Vacations
- Water Tower Place Vacations
- 875 North Michigan Avenue Vacations
- Museum of Contemporary Art Chicago Vacations
- 360 CHICAGO Vacations
- Northwestern Memorial Hospital Vacations
- Ann and Robert H. Lurie Children's Hospital Vacations
- Chicago Children's Museum Vacations
- Tribune Tower Vacations
- 900 North Michigan Shops Vacations
More AARP Member Vacation Packages
- Las Vegas Vacations
- New York Vacations
- Orlando Vacations
- Los Angeles Vacations
- Miami Vacations
- San Francisco Vacations
- New Orleans Vacations
- Chicago Vacations
- Fort Lauderdale Vacations
- Boston Vacations
- Honolulu Vacations
- San Diego Vacations
- Washington Vacations
- Toronto Vacations
- Anaheim Vacations
- Atlanta Vacations
- Nashville Vacations
- Seattle Vacations
- Phoenix Vacations
- Myrtle Beach Vacations
- Vancouver Vacations
- Palm Springs Vacations
- Denver Vacations
- Tampa Vacations
- Niagara Falls Vacations
- San Antonio Vacations
- Atlantic City Vacations
- Philadelphia Vacations
- Austin Vacations
- Dallas Vacations
More Types of Hotels
- Hotels with Air Conditioning in Streeterville
- Hotels with WiFi in Streeterville
- Family Hotels in Streeterville
- Hotels with Bars in Streeterville
- Hotel with wifi in Streeterville
- Hotel with a Concierge in Streeterville
- Smoke Free Hotels in Streeterville
- Beach Hotels in Streeterville
- Lakefront Hotels in Streeterville
- Luxury Hotels in Streeterville
- Hotels with a Pool in Streeterville
- Cheap Hotels in Streeterville
- Resorts & Hotels with Spas in Streeterville
- Pet-friendly Hotels in Streeterville
- Hotels with Early Check-in in Streeterville
- Hotels with Complimentary Breakfast in Streeterville
- Hotels with Hot Tubs in Streeterville
- Hotels with Balconies in Streeterville
- Hotels with an Indoor Pool in Streeterville
- Hotels with smoking rooms in Streeterville
- Hotels with Fireplaces in Streeterville
- Hotels on the River in Streeterville
- Oceanfront Hotels in Streeterville