Plan a trip to see Milwaukee Avenue

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

Hotel Riu Plaza Chicago

Downtown Chicago

￥228,866

per person

Jan 17 - Jan 21

found 12 hours ago

Roundtrip flight included

Tokyo (TYO) to Chicago (ORD)

9.4/10 Exceptional! (2,602 reviews)

Loved the hotel, the only negative thing I have to say is that I found it to be odd that there is no trash bags used in the trash cans in the rooms. Also, the bathroom has no vent for exhaust fan. Other than that, everything else was excellent, very clean facility, great breakfast selection.

Reviewed on Nov 4, 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

￥286,180

per person

Jan 17 - Jan 21

found 12 hours ago

Roundtrip flight included

Tokyo (TYO) to Chicago (ORD)

9.4/10 Exceptional! (1,761 reviews)

The Trump International Hotel was absolutely immaculate in appearance and the entire staff were fantastic in all aspects. The location is extremely desirable and within walking distance to numerous restaurants and attractions. However, my suite was somewhat underwhelming in regard to the bathroom. The deep soaking bathtub was smaller in scale than one would expect, and more specifically the shower head is set far too low for those of us who are six feet or taller. I would recommend this property.

Reviewed on Nov 3, 2025

Pendry Chicago

Downtown Chicago

￥251,615

per person

Jan 17 - Jan 21

found 12 hours ago

Roundtrip flight included

Tokyo (TYO) to Chicago (ORD)

9.4/10 Exceptional! (1,110 reviews)

We loved the Pendry!

Reviewed on Oct 27, 2025

Browse tours and tickets to explore Milwaukee Avenue

Tours & day trips

See all 190 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 60 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

See all 31 activities

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

Attractions

See all 20 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 16 activities

Rosemont: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

Northwestern College Chicago Campus

Enjoy the collegiate vibe at Northwestern College Chicago Campus as part of your travels around Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

The Gift Theatre

You can make plans for a show at The Gift Theatre on your trip to Chicago. Discover the top-notch restaurants and acclaimed art scene in this vibrant area.

Copernicus Center

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

Norwood Park Dog Park

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

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.

Six Corners

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