Streeterville Vacation Packages 2025/2026 from $339

Streeterville flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Hampton Inn Chicago-Carol Stream

Save 100% on your flight

per person

Jul 29 - Aug 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features an indoor pool and a 24-hour gym. There's no skimping on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. A 24-hour business center, express check-out, and dry cleaning are also on offer.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

per person

Aug 16 - Aug 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A restaurant is on site and multilingual staff is available around-the-clock at the 24-hour front desk. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like buffet breakfast and WiFi in public areas. There's a 24-hour gym on site, and a coffee shop and a snack bar/deli are also provided.

Wind Creek Southland Casino and Hotel

East Hazel Crest

Save 100% on your flight

per person

Sep 17 - Sep 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (MDW)

This resort features a casino, a full-service spa, and 4 restaurants. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Relax with a drink at one of the 3 bars/lounges and enjoy perks like free self parking.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

per person

Sep 11 - Sep 14

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

The Buckingham Hotel

Downtown Chicago

Save 100% on your flight

per person

Aug 16 - Aug 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a coffee shop, concierge services, and self parking. A 24-hour business center, a snack bar/deli, and luggage storage are also on offer.

Top Streeterville hotels deals

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

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A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.

Pet friendly

Free WiFi

The Wade

644 N Lake Shore Dr, Chicago, IL

Free Cancellation

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This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and express check-in are also provided.

Pool

Pet friendly

The Whitehall Hotel, BW Premier Collection

105 E Delaware Pl, Chicago, IL

Free Cancellation

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This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.

Breakfast included

Pet friendly

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

201 East Walton Place, Chicago, IL

Free Cancellation

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This hotel doesn't skimp on freebies - guests receive free full breakfast and free WiFi. Traveling on business? Take advantage of the business center, express check-out, and valet parking. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

Pet friendly

DoubleTree by Hilton Chicago - Magnificent Mile

300 E Ohio St, Chicago, IL

Free Cancellation

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This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. You'll appreciate the gym, poolside bar, and concierge services.

Pool

Pet friendly

Loews Chicago Hotel

455 North Park Drive, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

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This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and a coffee shop are also provided.

Pool

Pet friendly

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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.

Popular places to visit

Water Tower Place

4.5/5(834 reviews)

Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.

John Hancock Center

4.5/5(1,913 reviews)

You can find out about the history of Chicago with a visit to John Hancock Center. Amble around this vibrant area's lakeside or experience its acclaimed art scene.

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Chicago Children's Museum

4.5/5(196 reviews)

You can take time to visit Chicago Children's Museum during your travels to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

Frequently asked questions

How much are vacation packages to Streeterville?

With vacation packages available from just $339, it's not necessary to wipe out your bank balance for your getaway to Streeterville. Travelocity can help. Bundle up hotels, flights and tours into a package and receive some fantastic discounts. The more you book, the bigger the savings.

Where can I get the best vacation package deals for Streeterville?

For an amazing Streeterville package deal, turn to Travelocity. Pick from as many as 400 air carriers and 1,000,000 properties around the world to create your ultimate adventure --- the choice is all yours!

Why should I book my Streeterville vacation package with Travelocity?

Whether you're planning a month-long vacation or a last-minute trip, we have many amazing destinations to choose from at an affordable rate. What's more, we provide round-the-clock support, excellent service and a Price Match Guarantee. Save yourself money and time and book your dream vacation today.

Can I save money on my Streeterville car rental if I book it with hotels and flights?

Booking a Streeterville vacation package with Travelocity is an easy way to save you time and money. Pick a car, flight and hotel, or any combination of them, and score awesome discounts. You can also throw in a few tours and experiences. Once you've picked up the keys to the rental car, head out of the neighborhood and see what this location has to offer. Roughly 35 mi from Streeterville, Six Flags Great America is well worth a road trip.