Northwest Side Vacations from $511

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The Latest Northwest Side vacation packages

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection
Hotel Riu Plaza Chicago
Level Chicago Fulton Market
Pendry Chicago
Omni Chicago Hotel
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Northwest Side Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $144 total per night from Jul 6 to Jul 7
$144 total
Jul 6 - Jul 7
Total with taxes and fees
8/10 Very Good! (10,186 reviews)
"I would only stay here for the location or a one to two-night stay. No thermostat in the room so we needed a portable heater because it was so cold. The water pressure in the shower was pathetic and the tub didn't work. Our toilet was running and we had to have two separate calls to have it fixed. ..."

Reviewed on Jul 1, 2026

Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$181 nightly
The price is $215 total per night from Jul 5 to Jul 6
$215 total
Jul 5 - Jul 6
Total with taxes and fees
9.2/10 Wonderful! (1,826 reviews)
"Was excited to again stay with Omni but this property wasn’t up to the same standards as others we’ve stayed at… It was clean but just seemed “sad”"

Reviewed on Jul 1, 2026

Omni Chicago Hotel
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
$158 nightly
The price is $188 total per night from Jul 9 to Jul 10
$188 total
Jul 9 - Jul 10
Total with taxes and fees
9/10 Wonderful! (4,476 reviews)
"Bedsheets had stains upon arrival and the shower & sink faucet dials were loose."

Reviewed on Jul 1, 2026

Hilton Chicago/Magnificent Mile Suites
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.

Find the Best Northwest Side Vacation Packages

Northwest Side Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)

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