
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.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $725, price is now $511 per person
$511
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
The staff was very helpful. There were issues with the use of the TV but the staff was helpful with this.
Reviewed on Jul 5, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,010, price is now $619 per person
$619
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Awesome location for boat/beach/dining!
Reviewed on Jul 5, 2026

Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,267, price is now $789 per person
$789
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back.
The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.
Reviewed on Jul 2, 2026

The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,208, price is now $799 per person
$799
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
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 and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
Clean room. Great bar.
Reviewed on Jul 4, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,096, price is now $747 per person
$747
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
The staff here is absolutely perfection. They met all of our needs and are pleasant to speak with during your stay.
Reviewed on Jul 5, 2026

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,139, price is now $784 per person
$784
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
We generally stay here when we travel to Chicago by the quality of service has diminished lately. Additionally if your booking is through Expedia, everything gets complicated and not well treated.
Reviewed on Jul 5, 2026
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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 ...

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 ...

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 ...

The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
0.27 km from Streeterville
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 ...

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 ...

The Whitehall Hotel, BW Premier Collection
105 E Delaware Pl Chicago IL
0.7 km from Streeterville
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the restaurant and the helpful staff ...

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 ...

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 ...

Sheraton Grand Chicago Riverwalk
301 E North Water St Chicago IL
0.52 km from Streeterville
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 ...

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 ...

Hotel Saint Clair- Magnificent Mile
162 East Ontario Street Chicago IL
0.08 km from Streeterville
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 ...
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.

Wed, Aug 12 - Tue, Sep 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216 Roundtrip, just found
$216
Roundtrip
just found

Wed, Aug 12 - Tue, Sep 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$256 Roundtrip, just found
$256
Roundtrip
just found

Wed, Aug 12 - Tue, Sep 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$266 Roundtrip, just found
$266
Roundtrip
just found

Tue, Aug 11 - Sat, Aug 15
LAX
Los Angeles Intl.
MDW
Midway Intl.
$286 Roundtrip, found 2 days ago
$286
Roundtrip
found 2 days ago

Wed, Aug 12 - Tue, Sep 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$295 Roundtrip, just found
$295
Roundtrip
just found

