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Streeterville Vacation Packages

Streeterville Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Save 100% on your flight
Price was $725, price is now $483 per person
$483
per person
May 23 - May 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,173, price is now $716 per person
$716
per person
Jun 7 - Jun 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,215, price is now $790 per person
$790
per person
Jun 10 - Jun 14
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) 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 clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was $885, price is now $585 per person
$585
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was $1,134, price is now $759 per person
$759
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

3.5 out of 5
Price was $757, price is now $514 per person
$514
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Book a stay at this business-friendly hotel in Joliet. Enjoy free WiFi, 3 restaurants, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Route 66 Raceway and Harrah's Casino are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,788, price is now $1,215 per person
$1,215
per person
Jun 10 - Jun 14
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was $1,105, price is now $753 per person
$753
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
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 staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.

3-4 Night Vacations in Streeterville

Price found within the past 48 hours. Click for updated prices.
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

3.5 out of 5
Price was $757, price is now $514 per person
$514
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,207, price is now $835 per person
$835
per person
Jun 2 - Jun 5
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,589, price is now $1,108 per person
$1,108
per person
Jun 4 - Jun 7
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,509, price is now $1,059 per person
$1,059
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

5-7 Night Vacations in Streeterville

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,053, price is now $675 per person
$675
per person
Jun 12 - Jun 17
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,403, price is now $830 per person
$830
per person
Jun 12 - Jun 17
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,761, price is now $1,074 per person
$1,074
per person
Jun 12 - Jun 17
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,518, price is now $959 per person
$959
per person
Jun 12 - Jun 17
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Cheap Hotel Deals in Streeterville

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
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 ...
Opens in a new windowHilton Chicago/Magnificent Mile Suites
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
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 ...
Opens in a new windowHotel Riu Plaza Chicago
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
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. ...
Opens in a new windowAloft Chicago Mag Mile
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Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
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 ...
Opens in a new windowWarwick Allerton - Chicago
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
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 ...
Opens in a new windowDoubleTree by Hilton Chicago - Magnificent Mile
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
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 ...
Opens in a new windowThe Chicago Hotel Collection - Magnificent Mile
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
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 ...
Opens in a new windowThe Wade
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4 out of 5
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 ...
Opens in a new windowEmbassy Suites by Hilton Chicago Downtown Magnificent Mile
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

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Thu, May 28 - Wed, Jun 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$168 Roundtrip, found 3 hours ago
$168
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, May 28 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jun 3, priced at $168 found 3 hours ago
Frontier Airlines
Tue, May 19 - Thu, May 28
LAX
Los Angeles Intl.
MDW
Midway Intl.
$246 Roundtrip, found 3 hours ago
$246
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Tue, May 19 from Los Angeles Intl. to Midway Intl., returning Thu, May 28, priced at $246 found 3 hours ago
American Airlines
Mon, May 25 - Tue, May 26
LAX
Los Angeles Intl.
RFD
Greater Rockford
$315 Roundtrip, found 6 days ago
$315
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, May 25 from Los Angeles Intl. to Greater Rockford, returning Tue, May 26, priced at $315 found 6 days ago
ITA Airways
Wed, Jul 8 - Wed, Jul 22
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$924 Roundtrip, found 5 hours ago
$924
Roundtrip
found 5 hours ago
Select ITA Airways flight, departing Wed, Jul 8 from Fiumicino - Leonardo da Vinci Intl. to O'Hare Intl., returning Wed, Jul 22, priced at $924 found 5 hours ago