Maxwell Street Market

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was S$1,696, price is now S$786 per person
S$786
per person
6 May - 11 May
found 13 hours ago
Return direct flight included
Washington (IAD) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
This was a great stay! Really enjoyed the breakfast! Only down side was the shower. Water did not get hot and water pressure was horrible. Otherwise would have been 5 stars!

Reviewed on 21 Feb, 2026

The Wade

The Wade

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,402, price is now S$807 per person
S$807
per person
6 May - 11 May
found 13 hours ago
Return direct flight included
Washington (IAD) to Chicago (ORD)
8.4/10 Very Good! (1,444 reviews)
The lakeside view. Also the room was clean and spacious.

Reviewed on 19 Feb, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,998, price is now S$1,232 per person
S$1,232
per person
6 May - 11 May
found 13 hours ago
Return direct flight included
Washington (IAD) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
First off I want to give a special shout out to Eric! He assisted us so well in every way possible. I also didn’t expect it to be such a nice condo complex but I was so impressed by the rooms, amenities and the workers. Will definitely be coming back very soon!

Reviewed on 19 Feb, 2026

Tours & day trips

See all 163 activities
Flyover in Chicago

Flyover in Chicago

Activity duration is 30 minutes
9.8 out of 10 with 13 reviews
Free cancellation available
Price is S$48 per adult
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Private & custom tours

See all 58 activities
Chicago Cocktail Adventure Part 1

Chicago Cocktail Adventure Part 1

Activity duration is 3 hours
Free cancellation available
Price is S$6 per adult
Chicago Cocktail Adventure Part 1Opens in new tab

Food, drink & nightlife

See all 22 activities
Chicago's Chinatown Food and Walking Tour

Chicago's Chinatown Food and Walking Tour

Activity duration is 3 hours
10.0 out of 10 with 263 reviews
Free cancellation available
Price is S$101 per adult
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Attractions

See all 19 activities
Chicago CityPASS®: Experience 5 must-see attractions

Chicago CityPASS®: Experience 5 must-see attractions

Activity duration is 9 days
9.4 out of 10 with 795 reviews
Free cancellation available
Price is S$179 per adult
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Classes & workshops

See all 18 activities
BYOB Spray Paint and Sip at Studio W.I.P.

BYOB Spray Paint and Sip at Studio W.I.P.

Activity duration is 1 hour and 30 minutes
9.8 out of 10 with 235 reviews
Free cancellation available
Price is S$57 per adult
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Popular places to visit

Tri Taylor

University of Illinois Chicago

4.5/5(11 reviews)

Enjoy the student vibe at University of Illinois Chicago during your visit to Chicago. Stroll along the riverfront or experience the acclaimed art galleries in this vibrant area.

University of Illinois Chicago
Very nice terminal for the river taxi

Ping Tom Memorial Park

After visiting Ping Tom Memorial Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums.

Ping Tom Memorial Park
Willis Tower featuring a high-rise building, a city and mist or fog

Willis Tower

4.5/5(81 reviews)

The Skydeck at Willis Tower offers the best place in Chicago for a bird’s eye view across the breadth of the city and Lake Michigan.

Willis Tower
Chicago_SkydeckLedge_6125597_10

Skydeck Ledge

4.5/5(71 reviews)

You can find out about the history of Chicago when you stop by Skydeck Ledge. Discover the acclaimed art galleries and notable monuments in this vibrant area.

Skydeck Ledge
Park

Mary Bartelme Park

After visiting Mary Bartelme Park, make a plan to see the other sights and activities in Chicago. Experience the fascinating museums and acclaimed art galleries in this vibrant area.

Mary Bartelme Park

UIC Forum

Learn about the events happening in UIC Forum during your trip to Chicago. While you're in the area, find time to visit its shops.

UIC Forum

Top Maxwell Street Market Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Hilton Chicago
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Hotel Riu Plaza Chicago
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
55 E 11th Street Chicago IL
Hilton Garden Inn Chicago Downtown South Loop
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
Holiday Inn & Suites Chicago - Downtown by IHG
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
Travelodge by Wyndham Downtown Chicago
Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

3 out of 5
59 E. 11th Street Chicago IL
Homewood Suites by Hilton Chicago Downtown South Loop
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street Chicago IL
Crowne Plaza Chicago West Loop by IHG
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
1100 S Michigan Ave Chicago IL
Best Western Grant Park Hotel
See all 4,195 properties in Maxwell Street Market
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.

The Annual Holiday Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.