Milwaukee Avenue Tours and Activities

Milwaukee Avenue
Photo by Chandan Rastogi
Photo by Chandan Rastogi
Photo by Marc Jacobs
Photo by Marc Jacobs
Photo by Marc Jacobs
Photo by Marc Jacobs
Photo by Marc Jacobs
Photo by Marc Jacobs

Plan a trip to see Milwaukee Avenue

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

The Drake

4 out of 5
Downtown Chicago
Price was AU$1,183, price is now AU$808 per person
AU$808
per person
16 Nov - 19 Nov
found 15 hours ago
Return flight included
Greensboro (GSO) to Chicago (ORD)
8.8/10 Excellent! (1,291 reviews)
Great location and wonderful staff. Stayed with my family of four and we were able to easily get to all the wonderful sites we wanted to visit. The historic charm and lastige spaces enhanced our stay and our breakfast was superb.

Reviewed on 14 Oct 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$2,045, price is now AU$1,417 per person
AU$1,417
per person
16 Nov - 19 Nov
found 15 hours ago
Return flight included
Greensboro (GSO) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Excellent luxury atmosphere with second to none customer service. The bathroom was very nice. Although the toilet has a slight odor that was unexpected for the high quality room and hotel.

Reviewed on 15 Oct 2025

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was AU$1,193, price is now AU$850 per person
AU$850
per person
16 Nov - 19 Nov
found 15 hours ago
Return flight included
Greensboro (GSO) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
Hotel was clean and staff was friendly.

Reviewed on 15 Oct 2025

Tours & day trips

See all 166 activities
Architecture River Tour

Architecture River Tour

Activity duration is 1 hour and 15 minutes
9.6 out of 10 with 1486 reviews
Free cancellation available
Price is AU$75 per adult
Architecture River TourOpens in new tab

Private & custom tours

See all 33 activities
Eastside Chicago The Heist Exploration Game and Tour

Eastside Chicago The Heist Exploration Game and Tour

Activity duration is 1 hour and 35 minutes
Free cancellation available
Price is AU$14 per adult*
Eastside Chicago The Heist Exploration Game and TourOpens in new tab

Food, drink & nightlife

See all 27 activities
Chicago: Architecture Boat Tour with Drinks

Chicago: Architecture Boat Tour with Drinks

Activity duration is 1 hour and 30 minutes
9.0 out of 10 with 20 reviews
Free cancellation available
Price is AU$64 per adult
Chicago: Architecture Boat Tour with DrinksOpens in new tab

Attractions

See all 18 activities
360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Activity duration is 30 minutes
8.4 out of 10 with 671 reviews
Free cancellation available
Price is AU$45 per adult
360 CHICAGO Observation DeckOpens in new tab

Adventure & outdoor

See all 15 activities
Rosemont: Two Flight Indoor Skydiving Experience

Rosemont: Two Flight Indoor Skydiving Experience

Activity duration is 1 hour
6.6 out of 10 with 7 reviews
Free cancellation available
Price is AU$149 per traveller
Rosemont: Two Flight Indoor Skydiving ExperienceOpens in new tab

Popular places to visit

Northwestern College Chicago Campus

Walk around the campus at Northwestern College Chicago Campus during your visit to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

Northwestern College Chicago Campus

The Gift Theatre

You can make plans for a show at The Gift Theatre during your stay in Chicago. Discover the top-notch restaurants and acclaimed art galleries in this vibrant area.

The Gift Theatre

Copernicus Center

You can make plans for a show at Copernicus Center during your stay in Chicago. Amble around this vibrant area's lakeside or attend a sporting event.

Copernicus Center

Norwood Park Dog Park

After visiting Norwood Park Dog Park, make a plan to see the other sights and activities in Chicago.

Norwood Park Dog Park

Portage Park

After visiting Portage Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.

Portage Park

Six Corners

You can browse for the perfect souvenirs at Six Corners during your visit to Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.

Six Corners

Top Milwaukee Avenue Hotel & Accommodation Deals

Holiday Inn Chicago North Shore by IHG

Holiday Inn Chicago North Shore by IHG

3 out of 5
5300 West Touhy Ave, Skokie, IL
Holiday Inn Chicago North Shore by IHG
Motel Edgebrook Chicago North Shore by OYO

Motel Edgebrook Chicago North Shore by OYO

2 out of 5
6401 W Touhy Ave, Chicago, IL
Motel Edgebrook Chicago North Shore by OYO
Prime City Stay in a 1BR Apt

Prime City Stay in a 1BR Apt

Chicago
Prime City Stay in a 1BR Apt
SpringHill Suites Chicago O'Hare by Marriott

SpringHill Suites Chicago O'Hare by Marriott

3 out of 5
8101 West Higgins Road, Chicago, IL
SpringHill Suites Chicago O'Hare by Marriott
Holiday Inn Chicago O'Hare Area by IHG

Holiday Inn Chicago O'Hare Area by IHG

3 out of 5
5615 North Cumberland Avenue, Chicago, IL
Holiday Inn Chicago O'Hare Area by IHG
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road, Chicago, IL
Marriott Chicago O'Hare
Rodeway Inn Chicago - Evanston

Rodeway Inn Chicago - Evanston

2 out of 5
6155 N. JERSEY AVE, Chicago, IL
Rodeway Inn Chicago - Evanston
Renaissance Chicago O'Hare Suites Hotel

Renaissance Chicago O'Hare Suites Hotel

4 out of 5
8500 West Bryn Mawr Avenue, Chicago, IL
Renaissance Chicago O'Hare Suites Hotel
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
Hyatt Regency O'Hare Chicago
See all 4,381 properties in Milwaukee Avenue
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.