Best Flight From Luis Munoz Marin Intl. To CHI

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Amazing SJU to CHI Flight Deals

The cheapest flights to CHI-All Airports were $155 for round trip flights and $54 for one-way flights in the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, May 24 - Fri, May 29
SJU
San Juan
ORD
Chicago
$155 Roundtrip, found 3 days ago
$155
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, May 24 from San Juan to Chicago, returning Fri, May 29, priced at $155 found 3 days ago
Sun, May 24 - Fri, May 29
SJU
San Juan
ORD
Chicago
$176 Roundtrip, found 3 days ago
$176
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, May 24 from San Juan to Chicago, returning Fri, May 29, priced at $176 found 3 days ago
Sat, May 23 - Sun, May 24
SJU
San Juan
ORD
Chicago
$183 Roundtrip, found 13 hours ago
$183
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Sat, May 23 from San Juan to Chicago, returning Sun, May 24, priced at $183 found 13 hours ago
Sat, May 23 - Fri, May 29
SJU
San Juan
ORD
Chicago
$186 Roundtrip, found 13 hours ago
$186
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Sat, May 23 from San Juan to Chicago, returning Fri, May 29, priced at $186 found 13 hours ago
Thu, May 14 - Mon, May 18
SJU
San Juan
ORD
Chicago
$196 Roundtrip, found 4 days ago
$196
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, May 14 from San Juan to Chicago, returning Mon, May 18, priced at $196 found 4 days ago
Thu, May 7 - Sun, May 17
SJU
San Juan
ORD
Chicago
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, May 7 from San Juan to Chicago, returning Sun, May 17, priced at $199 found 1 day ago

Hotels near CHI-All Airports Airport (CHI)

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
The price is $148 total per night from May 25 to May 26
$148 total
per night
May 25 - May 26
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
8.2/10 Very Good! (2,648 reviews)
Clean room

Reviewed on Apr 30, 2026

Opens in a new windowHotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is $171 total per night from May 26 to May 27
$171 total
per night
May 26 - May 27
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
8.8/10 Excellent! (5,137 reviews)
Beautiful, clean room with an incredible downtown Chicago view. Totally worth it

Reviewed on Apr 29, 2026

Opens in a new windowRiver Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
The price is $138 total per night from May 25 to May 26
$138 total
per night
May 25 - May 26
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
8.8/10 Excellent! (3,479 reviews)
Great check in and check out experience

Reviewed on Apr 29, 2026

Opens in a new windowClub Quarters Hotel, Central Loop, Chicago
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Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
The price is $252 total per night from May 23 to May 24
$252 total
per night
May 23 - May 24
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and The Dome at the Parkway Bank Sports Complex are located nearby.
8.4/10 Very Good! (2,282 reviews)
After two international flights this was a welcome overnight and we loved the view of the airport and downtown from our room. The restaurant was decent for a quick bite, and when our coffee machine didn’t work, they kindly gave us a voucher to buy one at their cafe. Comfortable overall stay with ...

Reviewed on Apr 29, 2026

Opens in a new windowHilton Chicago O'Hare Airport
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
The price is $178 total per night from May 25 to May 26
$178 total
per night
May 25 - May 26
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
9.4/10 Exceptional! (4,001 reviews)
The best breakfast buffet I’ve ever had!

Reviewed on Apr 29, 2026

Opens in a new windowHotel Riu Plaza Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
The price is $165 total per night from May 10 to May 11
$165 total
per night
May 10 - May 11
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
9/10 Wonderful! (4,230 reviews)
The location was awesome. So close to everything! Hotel staff were always helpful & friendly. Definitely would stay again.

Reviewed on Apr 29, 2026

Opens in a new windowHilton Chicago/Magnificent Mile Suites
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2 Chicago IL
The price is $177 total per night from May 25 to May 26
$177 total
per night
May 25 - May 26
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
8.8/10 Excellent! (2,293 reviews)
Breakfast was nice and the view was even better

Reviewed on Apr 28, 2026

Opens in a new windowHoliday Inn Chicago Dwtn - The Mart by IHG
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is $147 total per night from May 8 to May 9
$147 total
per night
May 8 - May 9
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
8/10 Very Good! (10,169 reviews)
The room was clean and quiet, the staff was nice, and the location is great! (We used the grant park south garage to park our car.)

Reviewed on Apr 30, 2026

Opens in a new windowCongress Plaza Hotel
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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.

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.