Hotels in Oak Street, IL: Compare 10+ Sites & Save

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587 Best Hotels in Oak Street (Starting from $123)

Thompson Chicago, by Hyatt
Thompson Chicago, by Hyatt
Hotel
Chicago, IL, USA
0.1k from Oak Street center

Accommodations, Parking, Romantic, Boutique, Pet-friendly, 4-star, Lodgings, Places to stay, Family

8.8

Fabulous

358 reviews

$210
Average price / night
Check Availability
The Talbott, Autograph Collection
The Talbott, Autograph Collection
Hotel
Chicago, IL, USA
0.2k from Oak Street center

Accommodations, Parking, Romantic, Pet-friendly, 4-star, Lodgings, Places to stay, Family, Accessible hotels

7.3

Good

14 reviews

$285
Average price / night
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Heart of Chicago, Double Queen @ The Chicago Hotel Collection Magnificent Mile
Heart of Chicago, Double Queen @ The Chicago Hotel Collection Magnificent Mile
Hotel
Chicago, IL, 60611, United States
0.2k from Oak Street center

AC, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, TV

2.0

Review score

1 reviews

$322
Average price / night
Check Availability
Four Seasons Chicago
Four Seasons Chicago
Hotel
Chicago, IL, USA
0.2k from Oak Street center

Luxury, Cheap, Accommodations, Pools, Parking, Spa, Romantic, Pet-friendly, 5-star

8.9

Fabulous

158 reviews

$663
Average price / night
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The Chicago Hotel Collection Magnificent Mile Sleek Standard Double Queen
The Chicago Hotel Collection Magnificent Mile Sleek Standard Double Queen
Hotel
Chicago, IL, 60611, United States
0.2k from Oak Street center

AC, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, TV

7.4

Good

3 reviews

$159
Average price / night
Check Availability
Waldorf Astoria Chicago
Waldorf Astoria Chicago
Hotel
Chicago, IL, USA
0.2k from Oak Street center

Luxury, Accommodations, Pools, Parking, Spa, Boutique, Pet-friendly, 5-star, Lodgings

9.1

Superb

120 reviews

$694
Average price / night
Check Availability
The Chicago Hotel Collection, Mag Mile, Deluxe Double Queen - Premium Option
The Chicago Hotel Collection, Mag Mile, Deluxe Double Queen - Premium Option
Hotel
Chicago, IL, 60611, United States
0.2k from Oak Street center

AC, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, TV

10.0

Exceptional

1 reviews

$160
Average price / night
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The Drake Hotel
The Drake Hotel
Hotel
Chicago, IL, USA
0.2k from Oak Street center

Accommodations, Parking, Romantic, Boutique, Hilton , Pet-friendly, 4-star, Lodgings, Places to stay

8.3

Very Good

596 reviews

$198
Average price / night
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The Drake
The Drake
Hotel
140 E Walton Place, Chicago, IL, 60611, United States
0.2k from Oak Street center

AC, Bar, Breakfast Available, Business Services, Crib, Elevator, Extra Bed, Fitness Equipment, Frontdesk 24 Hour

9.0

Fabulous

1421 reviews

$177
Average price / night
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The Whitehall Hotel - BW Premier Collection
The Whitehall Hotel - BW Premier Collection
Hotel
Chicago, IL, USA
0.2k from Oak Street center

Accommodations, Parking, Pet-friendly, 3-star, Lodgings, Places to stay, Accessible hotels

7.7

Good

1108 reviews

$149
Average price / night
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Millennium Knickerbocker Chicago
Millennium Knickerbocker Chicago
Hotel
Chicago, IL, USA
0.3k from Oak Street center

Wheelchair Accessible, Air Conditioner, Fireplace/Heating, Tv, Security/Safety, Parking, Sports/Activities

8.0

Good

1661 reviews

$156
Average price / night
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The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
Hotel
909 North Michigan Ave, Chicago, IL, 60611, United States
0.2k from Oak Street center

AC, Bar, Breakfast Available, Business Services, Elevator, Extra Bed, Fitness Equipment, Frontdesk 24 Hour, Heater

8.8

Fabulous

1113 reviews

$179
Average price / night
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Sofitel Chicago Magnificent Mile
Sofitel Chicago Magnificent Mile
Hotel
Chicago, IL, USA
0.3k from Oak Street center

Luxury, Accommodations, Parking, Romantic, Boutique, Pet-friendly, 5-star, Lodgings, Places to stay

8.8

Fabulous

1397 reviews

$256
Average price / night
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Four Seasons Hotel Chicago
Four Seasons Hotel Chicago
Hotel
120 East Delaware Place, Chicago, IL, 60611, United States
0.2k from Oak Street center

AC, Bar, Breakfast Available, Business Services, Crib, Elevator, Fitness Equipment, Frontdesk 24 Hour, Housekeeping

9.4

Superb

1003 reviews

$469
Average price / night
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Sonesta ES Suites Chicago Downtown Magnificent Mile Medical
Sonesta ES Suites Chicago Downtown Magnificent Mile Medical
Hotel
Chicago, IL, USA
0.4k from Oak Street center

Cheap, Accommodations, Parking, Romantic, Pet-friendly, 3-star, Lodgings, Places to stay, Self-catering

8.1

Very Good

2502 reviews

$179
Average price / night
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Hilton Chicago Magnificent Mile Suites
Hilton Chicago Magnificent Mile Suites
Hotel
Chicago, IL, USA
0.4k from Oak Street center

Accommodations, Parking, Romantic, Hilton , Pet-friendly, 3-star, Lodgings, Places to stay, Accessible hotels

8.5

Very Good

1908 reviews

$161
Average price / night
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2 Connecting Suites at a 4⭐️ Hotel
2 Connecting Suites at a 4⭐️ Hotel
Hotel
Chicago, IL, 60611, United States
0.2k from Oak Street center

AC, Crib, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Living Area, Microwave

New to Booking
$699
Average price / night
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Park Hyatt Chicago
Park Hyatt Chicago
Hotel
Chicago, IL, USA
0.4k from Oak Street center

Luxury, Cheap, Accommodations, Pools, Parking, Spa, Boutique, Pet-friendly, 5-star

9.2

Superb

86 reviews

$551
Average price / night
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2 Connecting Suites at a 5⭐️ Hotel
2 Connecting Suites at a 5⭐️ Hotel
Hotel
Chicago, IL, 60611, United States
0.2k from Oak Street center

AC, Balcony, Crib, Elevator, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

New to Booking
$3330
Average price / night
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The Peninsula Chicago
The Peninsula Chicago
Hotel
Chicago, IL, USA
0.5k from Oak Street center

Accommodations, Pools, Parking, Spa, Romantic, Boutique, Pet-friendly, 5-star, Lodgings

9.4

Superb

248 reviews

$625
Average price / night
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The Ritz-Carlton, Chicago
The Ritz-Carlton, Chicago
Hotel
Chicago, IL, USA
0.5k from Oak Street center

Luxury, Accommodations, Pools, Parking, Spa, Romantic, Pet-friendly, 5-star, Lodgings

8.6

Fabulous

54 reviews

$492
Average price / night
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Modern Digs Steps from Mag Mile Shops/Dining with 24-hour Gym
Modern Digs Steps from Mag Mile Shops/Dining with 24-hour Gym
Hotel
Chicago, IL, 60611, United States
0.3k from Oak Street center

AC, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, TV

New to Booking
$158
Average price / night
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Claridge House
Claridge House
Hotel
Chicago, IL, USA
0.6k from Oak Street center

Cheap, Accommodations, Parking, Spa, Boutique, Pet-friendly, 4-star, Lodgings, Places to stay

8.4

Very Good

582 reviews

$234
Average price / night
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Hampton Inn Chicago Downtown/Magnificent Mile
Hampton Inn Chicago Downtown/Magnificent Mile
Hotel
Chicago, IL, USA
0.7k from Oak Street center

Accommodations, Parking, Romantic, Pet-friendly, 3-star, Lodgings, Places to stay, Accessible hotels

7.6

Good

578 reviews

$166
Average price / night
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Omni Chicago Hotel
Omni Chicago Hotel
Hotel
Chicago, IL, USA
0.7k from Oak Street center

Cheap, Accommodations, Parking, Pet-friendly, 4-star, Lodgings, Places to stay, Family, Accessible hotels

8.6

Fabulous

918 reviews

$266
Average price / night
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Residence Inn by Marriott Chicago Downtown Magnificent Mile
Residence Inn by Marriott Chicago Downtown Magnificent Mile
Hotel
Oak Street, Chicago, Illinois, USA
0.7k from Oak Street center

Luxury, Cheap, Accommodations, Parking, Pet-friendly, 5-star, Lodgings, Places to stay, Family

9.0

Fabulous

230 reviews

$199
Average price / night
Check Availability
Warwick Allerton Chicago
Warwick Allerton Chicago
Hotel
Oak Street, Chicago, Illinois, USA
0.7k from Oak Street center

Cheap, Accommodations, Parking, Romantic, Boutique, 4-star, Lodgings, Places to stay, Family

8.3

Very Good

6820 reviews

$123
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Hotels in Oak Street.

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Oak Street Hotels on the Map

Frequently Asked Questions

You can explore 587 verified hotels in Oak Street. These include a range of options from luxury resorts and boutique hotels to budget-friendly accommodations suitable for different travel styles.

Hotel prices in Oak Street vary depending on the season, location, and property type. Rates typically start from around $123 per night, with higher prices for premium hotels, central locations, or peak travel dates.

Most hotels in Oak Street include amenities such as Guest Services, Accessibility, and Wheelchair Accessible. Additional features like breakfast, parking, or resort facilities may vary by property, so it’s helpful to review the details before booking.

You can identify top-rated hotels in Oak Street by sorting listings based on guest ratings and reviews. Looking at recent feedback, overall scores, and review volume can help you find properties that consistently deliver a high-quality experience.

For popular travel periods or busy locations, booking 30 to 60 days in advance is generally recommended to secure preferred options. During quieter periods, you may find more flexibility and availability closer to your travel dates.

Yes, some hotels in Oak Street welcome pets. Currently, 37 listings allow pets, although policies may vary. It’s a good idea to review any pet-related rules before booking.

Many hotels in Oak Street offer flexible or refundable booking options. Checking the cancellation policy before confirming your reservation can help you choose a rate that suits your travel plans.