Milwaukee Avenue

A nighttime cityscape with illuminated buildings and a river.
A mural with the word "CHICAGO" and various city elements.
Two red drinks on a table with a fire extinguisher and a directional sign in the background.

Plan a trip to see Milwaukee Avenue

Price found within the past 48 hours. Click for updated prices.
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,449, price is now £931 per person
£931
per person
7 Nov - 12 Nov
found 21 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,906, price is now £1,159 per person
£1,159
per person
7 Nov - 12 Nov
found 21 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Amazing hotel. We go every year and always have a great time. We were greeted with a warm hand towel and champagne.

Reviewed on 19 Aug 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,454, price is now £940 per person
£940
per person
7 Nov - 12 Nov
found 21 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Beautiful room & View!! Will definitely book again!

Reviewed on 19 Aug 2026

Tours & day trips

See all 265 activities
Architecture River Tour

Architecture River Tour

Activity duration is 1 hour
9.6 out of 10 with 1615 reviews
Free cancellation available
Price is £29 per adult
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Private & custom tours

See all 66 activities
Chicago: Shooting & Spinning Art Experience (Neon Lights)

Chicago: Shooting & Spinning Art Experience (Neon Lights)

Activity duration is 45 minutes
Free cancellation available
Price is £84 per adult
Chicago: Shooting & Spinning Art Experience (Neon Lights)Opens in new tab

Food, drink & nightlife

See all 39 activities
City Cruises Chicago: Lake Michigan Premier Dinner Cruise

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

Activity duration is 2 hours and 30 minutes
8.2 out of 10 with 42 reviews
Price is £117 per adult
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Classes & workshops

See all 30 activities
Chicago: BYOB Spray Paint and Sip Workshop

Chicago: BYOB Spray Paint and Sip Workshop

Activity duration is 1 hour and 30 minutes
10.0 out of 10 with 15 reviews
Free cancellation available
Price is £30 per adult
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Attractions

See all 22 activities
360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Activity duration is 2 hours
8.6 out of 10 with 735 reviews
Free cancellation available
Price is £22 per adult
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Stay near popular Milwaukee Avenue attractions

Milwaukee Avenue

You can search for that perfect souvenir at Milwaukee Avenue during your trip to Chicago. Experience the live music and theatre scene in this vibrant area.
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Top Hotel Deals

Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater

Chicago IL
Sleeps 18 • 8BR • Game Room • Gym • Theater
Holiday Inn & Suites Chicago North Shore (Skokie) by IHG

Holiday Inn & Suites Chicago North Shore (Skokie) by IHG

3 out of 5
5300 West Touhy Ave Skokie IL
Holiday Inn & Suites Chicago North Shore (Skokie) 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
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
Your Chicago Home Base – 4BR, 2BA, Sleeps 15, Ideal for Families & Groups!

Your Chicago Home Base – 4BR, 2BA, Sleeps 15, Ideal for Families & Groups!

Chicago IL
Your Chicago Home Base – 4BR, 2BA, Sleeps 15, Ideal for Families & Groups!
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
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
Holiday Inn Express & Suites Chicago North Shore - Niles by IHG

Holiday Inn Express & Suites Chicago North Shore - Niles by IHG

2.5 out of 5
7247 North Waukegan Road Niles IL
Holiday Inn Express & Suites Chicago North Shore - Niles by IHG
Rodeway Inn Chicago - Evanston

Rodeway Inn Chicago - Evanston

2 out of 5
6155 N. JERSEY AVE Chicago IL
Rodeway Inn Chicago - Evanston
See all 4,349 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.