Streeterville Trip

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Price found within the past 48 hours. Click for updated prices.
  • Exterior
    Jul 24 - Jul 26

    Warwick Allerton - Chicago + Flight

    Downtown Chicago
    2 nights
    4.0 star property
    8.6/10 - Excellent (3,046 reviews)
    "Great location. Very nice"
    Reviewed June 5, 2026
    Return • Portland (PDX) - Chicago (MDW)
    PDX - MDW • 1 stop ORD - PDX • 1 stop
    ₹90,680
    ₹72,211
    per traveller
    found 16 hours ago
    Warwick Allerton - Chicago
  • Front of property
    Jul 24 - Jul 26

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    2 nights
    4.0 star property
    9.4/10 - Exceptional (4,361 reviews)
    "Excelente atención de todo el personal del hotel. Muy limpio todo, un desayuno super bueno y muy variado. El rooftop con excelente servicio y ofertas, además de vistas increíbles. Excelente ubicación. Definitivamente la cadena hotelera Riu se ha convertido en mi favorita para cualquier destino🤗"
    Reviewed June 5, 2026
    Return • Portland (PDX) - Chicago (MDW)
    PDX - MDW • 1 stop ORD - PDX • 1 stop
    ₹117,838
    ₹83,112
    per traveller
    found 16 hours ago
    Hotel Riu Plaza Chicago
  • Full-sized fridge, microwave, oven, stovetop
    Jul 24 - Jul 26

    Level Chicago – Old Town + Flight

    Downtown Chicago
    2 nights
    4.0 star property
    9.0/10 - Wonderful (488 reviews)
    "Very clean and loved the location and amenities with the store on the first floor was fantastic"
    Reviewed June 3, 2026
    Return • Portland (PDX) - Chicago (MDW)
    PDX - MDW • 1 stop ORD - PDX • 1 stop
    ₹114,959
    ₹83,869
    per traveller
    found 16 hours ago
    Level Chicago – Old Town
  • Lobby
    Jul 24 - Jul 26

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    2 nights
    4.0 star property
    8.2/10 - Very good (2,758 reviews)
    "The staff were friendly and helpful."
    Reviewed June 5, 2026
    Return • Portland (PDX) - Chicago (MDW)
    PDX - MDW • 1 stop ORD - PDX • 1 stop
    ₹100,444
    ₹76,229
    per traveller
    found 16 hours ago
    Hotel Felix River North/Magnificent Mile
  • Exterior detail
    Jul 24 - Jul 26

    The Emily Hotel + Flight

    Downtown Chicago
    2 nights
    4.0 star property
    9.2/10 - Wonderful (1,322 reviews)
    "Great gym. I like that there was a coffee shop downstairs as well. Room was very clean and comfortable."
    Reviewed June 5, 2026
    Return • Portland (PDX) - Chicago (MDW)
    PDX - MDW • 1 stop ORD - PDX • 1 stop
    ₹96,771
    ₹74,906
    per traveller
    found 16 hours ago
    The Emily Hotel

Where to stay in Streeterville

Find the best Streeterville areas and neighborhoods for the activities you enjoy most. Learn more about Streeterville
Downtown Chicago

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Top hotels in Streeterville

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is ₹14,431 per night from 28 Jun to 29 Jun
₹14,431
₹17,157 total
28 Jun - 29 Jun
includes taxes & fees
7.8/10 Good! (1,525 reviews)
"Great location, lovely hotel with a roof top bar and cheerful staff."

Reviewed on 6 Jun 2026

The Chicago Hotel Collection - Magnificent Mile
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₹17,945 per night from 30 Jun to 1 Jul
₹17,945
₹24,041 total
30 Jun - 1 Jul
includes taxes & fees
9.4/10 Exceptional! (4,361 reviews)
"Excelente atención de todo el personal del hotel. Muy limpio todo, un desayuno super bueno y muy variado. El rooftop con excelente servicio y ofertas, además de vistas increíbles. Excelente ubicación. Definitivamente la cadena hotelera Riu se ha convertido en mi favorita para cualquier destino🤗"

Reviewed on 5 Jun 2026

Hotel Riu Plaza Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₹15,190 per night from 7 Jul to 8 Jul
₹15,190
₹18,059 total
7 Jul - 8 Jul
includes taxes & fees
9/10 Wonderful! (4,381 reviews)
"I stay here often and am always greeted by a kind staff. Room is always clean and the area is nice."

Reviewed on 6 Jun 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,582 properties in Streeterville
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.

Frequently asked questions

How much does a Streeterville holiday package cost?
Maybe less than you might think — from as low as , in fact! By bundling hotels, flights and car rentals into a custom-built holiday package, your Streeterville escape is just clicks away.
How do I get a cheap travel package to Streeterville?
Combine your flight and hotel bookings, throw in extras such as a rental car or activities, and save with a Streeterville holiday package. You won't just pick up amazing discounts on your adventure — you'll have loads of choice at your fingertips too. When you book through Expedia, you'll have your pick of over 550 partner airlines and 1,000,000 hotels throughout the world. Your dream holiday starts right here, right now!
Where should I stay in Streeterville?
Most people who travel to Streeterville include both McCormick Place and Millennium Park on their must-see lists. Why not reserve a hotel near these main attractions?
What are the top hotels in Streeterville?
Make a reservation at Sable at Navy Pier Chicago, Curio Collection by Hilton. It's one of the neighbourhood's most in-demand hotels. Another well-known option in Streeterville is Omni Chicago Hotel.
How far in advance should I book my Streeterville holiday?
Travellers are usually able to browse international flights on Expedia up to 12 months prior to departure. Booking at the last minute? With a stroke of luck, it's still possible to score a cheap ticket only weeks before your journey.
What does an Expedia Streeterville travel package include?
Flights, hotels and a cool car for all your fun road trip adventures. Simply pick and choose your preferred bundle and gain access to great discounts. Once you've made your booking, add on a couple of activities and tours and watch your savings pile up. When it comes to crafting your Streeterville getaway, you're in charge!
What should I know before booking a Streeterville travel package?
Booking all the parts of your getaway together is one of the easiest ways to save. Bundle your car rentals, airfares and hotels into a neat package. But you're not restricted to hotels. Expedia offers all sorts of properties, including holiday rentals such as mountain cabins and spacious residences. The list goes on!
Can I choose my airline with a Streeterville Expedia holiday package?
Expedia offers access to more than 550 airline partners worldwide, so you definitely can. Just select the carrier you want and create your ideal Streeterville holiday.
If I'm not able to travel, can I cancel my Streeterville holiday package?
Yes you can, and we're here to help. You may be able to cancel or amend your Streeterville holiday package for free if you booked in the last 24 hours. However, you may be charged a fee by your hotel, airline or car rental company if you booked more than 24 hours ago. If your circumstances unexpectedly change, browse our Customer Service Portal for more information.

Popular places to visit

Water Tower Place

Water Tower Place

4/5(25 reviews)

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

Water Tower Place
900 North Michigan Shops

900 North Michigan Shops

5/5(1 review)

You can browse for the perfect souvenirs at 900 North Michigan Shops during your trip to Chicago. Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.

900 North Michigan Shops
Chicago Children's Museum

Chicago Children's Museum

4/5(1 review)

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 galleries.

Chicago Children's Museum
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.