Streeterville Vacation Packages 2025/2026 from $280

Streeterville flight + hotel vacation packages

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

Holiday Inn Chicago O'Hare – Rosemont by IHG

O'Hare

Save 100% on your flight

$280

per person

Oct 31 - Nov 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Self parking, a coffee shop, and a grocery/convenience store are also offered.

The Emily Hotel

Downtown Chicago

$673

per person

Oct 31 - Nov 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.

Level Chicago – Old Town

Downtown Chicago

$519

per person

Oct 31 - Nov 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.

Palmer House a Hilton Hotel

Downtown Chicago

Save 100% on your flight

$584

per person

Oct 31 - Nov 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and limo/town car service.

Hilton Chicago

Downtown Chicago

Save 100% on your flight

$506

per person

Nov 10 - Nov 16

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.

Top Streeterville hotels deals

The Wade

644 N Lake Shore Dr, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$167 nightly

$196 total

Sep 22 - Sep 23

Total with taxes and fees

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

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$161 nightly

$189 total

Sep 22 - Sep 23

Total with taxes and fees

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 Whitehall Hotel, BW Premier Collection

105 E Delaware Pl, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$139 nightly

$163 total

Sep 24 - Sep 25

Total with taxes and fees

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

The Chicago Hotel Collection - Magnificent Mile

166 E Superior Street, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$141 nightly

$166 total

Sep 2 - Sep 3

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. There's luggage storage and multilingual staff can provide around-the-clock assistance.

Pet friendly

Free WiFi

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

201 East Walton Place, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$161 nightly

$189 total

Sep 4 - Sep 5

Total with taxes and fees

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

Reserve now, pay when you stay

$168 nightly

$198 total

Sep 3 - Sep 4

Total with taxes and fees

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

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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

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

John Hancock Center

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 theater scene.

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Chicago Children's Museum

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 art scene.

Frequently asked questions

How much are vacation packages to Streeterville?

With vacation packages available from just $280, 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.