Streeterville Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Streeterville Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Illinois Beach Hotel
Save 100% on your flight
Price was $453, price is now $300 per person
$300
per person
May 19 - May 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this hotel in Zion. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Illinois Beach State Park and Carmel Park are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,167, price is now $636 per person
$636
per person
May 19 - May 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $2,487, price is now $1,456 per person
$1,456
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,967, price is now $1,238 per person
$1,238
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip flight included
Raleigh (RDU) 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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $728, price is now $470 per person
$470
per person
May 19 - May 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $1,003, price is now $652 per person
$652
per person
May 19 - May 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
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Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
0.11 km from Streeterville
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 ...
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
0.71 km from Streeterville
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 ...
Aloft Chicago Mag Mile
243 E. Ontario Chicago IL
0.07 km from Streeterville
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. ...
The Wade
644 N Lake Shore Dr Chicago IL
0.55 km from Streeterville
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
Courtyard by Marriott Chicago Magnificent Mile
165 East Ontario Street Chicago IL
0.06 km from Streeterville
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
DoubleTree by Hilton Chicago - Magnificent Mile
300 E Ohio St Chicago IL
0.2 km from Streeterville
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 ...
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
201 East Walton Place Chicago IL
0.74 km from Streeterville
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 ...
Sable at Navy Pier Chicago, Curio Collection by Hilton
900 E Grand Chicago IL
1.53 km from Streeterville
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 ...
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
511 North Columbus Drive Chicago IL
0.27 km from Streeterville
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 ...
Chicago Marriott Downtown Magnificent Mile
540 North Michigan Avenue Chicago IL
0.28 km from Streeterville
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the ...
Ivy Boutique Hotel
233 E Ontario Chicago IL
0.05 km from Streeterville
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean ...
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
0.28 km from Streeterville
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 ...
Warwick Allerton - Chicago
701 North Michigan Avenue Chicago IL
0.25 km from Streeterville
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 ...
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.
Sat, May 9 - Sat, May 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$118 Roundtrip, just found
$118
Roundtrip
just found
Wed, Apr 22 - Sat, May 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$160 Roundtrip, found 4 hours ago
$160
Roundtrip
found 4 hours ago
Sat, May 9 - Sat, May 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237 Roundtrip, just found
$237
Roundtrip
just found
Wed, May 13 - Sat, May 16
LAX
Los Angeles Intl.
MDW
Midway Intl.
$247 Roundtrip, found 1 day ago
$247
Roundtrip
found 1 day ago
Sat, May 9 - Sat, May 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$257 Roundtrip, just found
$257
Roundtrip
just found