We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
Review Highlights
Quiet Now

It was a late afternoon hour, and I found myself walking along Oak Street towards N Michigan... read more

Reviewed September 16, 2018
irina g
A nice stroll

Stroll along a very upscale street that comes off Michigan Ave. it is lined with upscale shops and... read more

Reviewed September 13, 2018
Las Vegas, Nevada
via mobile
Read all 71 reviews
All photos (21)
Full view
Traveler Overview
  • Excellent43%
  • Very good48%
  • Average9%
  • Poor0%
  • Terrible0%
Travelers talk about
“window shopping”(10 reviews)
“jimmy choo”(4 reviews)
“rush street”(4 reviews)
This downtown street is filled with upscale shopping opportunities.
As featured in Highlights of Chicago
32 E Oak St # 200, State St. to Michigan Ave., Chicago, IL 60611-1297
Near North Side
Improve This Listing
Recommended experiences in and around Chicago
from $47.00
More Info
from $27.00
More Info
from $22.00
More Info
from $25.76
More Info
Reviews (71)
Filter reviews
54 results
Traveler rating
Traveler type
Time of year
More languages
Traveler rating
Show reviews that mention
All reviews window shopping jimmy choo rush street north michigan avenue short street giorgio armani kate spade upscale shops high end shops ted baker van cleef tory burch luxury brands chicago's gold coast clothing stores rodeo drive drake hotel
Selected filters
Updating list...
1 - 10 of 54 reviews
Reviewed September 16, 2018

It was a late afternoon hour, and I found myself walking along Oak Street towards N Michigan Ave. Oak Street is of course famous for its high-end, luxury shops. These shops didn't look overly busy with customers at that hour. Saw a couple of Lamborghinis...More

Date of experience: September 2018
Thank irina g
Reviewed September 13, 2018 via mobile

Stroll along a very upscale street that comes off Michigan Ave. it is lined with upscale shops and restaurants. It covers some of the more exclusive parts of the city. The more distinguished residents of Chicago live in and around here.

Date of experience: August 2018
Thank McWett
Reviewed September 4, 2018

Oak Street isn't as celebrated as North Michigan Avenue, more commonly referred to as The Magnificent Mile, but it is to Chicago what Rodeo Drive is to Beverly Hills and Worth Avenue is to Palm Beach. Oak Street, a short street in Chicago's Gold Coast...More

Date of experience: September 2018
Thank Taylor B
Reviewed August 30, 2018 via mobile

This is designer shop heaven. Every shop on this street just yells style and splendour. Love how people just drive up and someone valley parks their cars for them . Street for the rich and want to be footballers wives.

Date of experience: August 2018
Thank ian_dempster
Reviewed August 27, 2018

The lovely tree-lined street is perfect for strolling, people watching, and window shopping at both trendy and high-end designer boutiques. Located just off Michigan Avenue (The Mag Mile), you'll be able to complete your shopping or just-looking experience. You'll find unique and one-of-kind fashionable items...More

Date of experience: August 2018
Thank johnnolf
Reviewed April 29, 2018 via mobile

This is a street that leads from the beach and crosses near North side. It’s full of upscale shops, some still under construction, and tends to be busy and crowded around the weekend. If you’re staying in the area, or are a fashionista (the Versace...More

Date of experience: April 2018
Thank Nicolas_Kar
Reviewed April 9, 2018 via mobile

Oak street has lots of high end clothing stores. It’s a really nice and well maintained street. Some nice bars and restaurants on here too. Would recommend a visit

Date of experience: March 2018
Thank Ianbb8
Reviewed March 19, 2018 via mobile

Lots of high end shops. Definitely window shopping for me, but fun none the less. I as close by my hotel and passed this area on my way to Lake Michigan.

Date of experience: March 2018
1  Thank Brilynn1979
Reviewed March 3, 2018 via mobile

Went here with a friend. Service was fast, courteous, and efficient. Really friendly and warm staff who enhanced the delicious meal.

Date of experience: March 2018
Thank bl0ndezilla
Reviewed November 27, 2017

Quaint shops in an intimate area that feels more like a neighborhood than a commercial area. Many restaurants and bars nearby to pass the time.

Date of experience: October 2017
Thank JLo5424
View more reviews
Gold Coast
Located just north of The Loop, Gold Coast is one of
Chicago’s most affluent and popular neighborhoods. The
original Playboy, Hugh Hefner, once had a mansion
here. In addition to prestigious hotels, historic
mansions and luxury high-rise apartments, you’ll also
find upscale specialty boutiques and Michelin-starred
restaurants. Walk along Oak Street for your shopping
fix and dance through the night along Rush Street. The
Nearby HotelsSee all 205 nearby hotels
Thompson Chicago
2,780 reviews
.05 miles away
Waldorf Astoria Chicago
2,827 reviews
.08 miles away
The Talbott Hotel
4,026 reviews
.12 miles away
Delaware Towers
3 reviews
.13 miles away
Nearby RestaurantsSee all 11,213 nearby restaurants
Gibsons Bar & Steakhouse
3,639 reviews
.07 miles away
The Original Pancake House
937 reviews
.06 miles away
Hugo's Frog Bar & Fish House
1,463 reviews
.05 miles away
421 reviews
.06 miles away
Nearby AttractionsSee all 2,298 nearby attractions
Mariano Plaza
7 reviews
.05 miles away
5 reviews
.02 miles away
Channing's Day Spa
8 reviews
.04 miles away
Questions & Answers
Get quick answers from Oak Street staff and past visitors.
Note: your question will be posted publicly on the Questions & Answers page.
Posting guidelines