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 $87 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 6 days ago
$155
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sun, May 24 from San Juan to Chicago, returning Fri, May 29, priced at $155 found 6 days ago
Sun, May 24 - Fri, May 29
SJU
San Juan
ORD
Chicago
$176 Roundtrip, found 6 days ago
$176
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sun, May 24 from San Juan to Chicago, returning Fri, May 29, priced at $176 found 6 days ago
Sat, May 23 - Sun, May 24
SJU
San Juan
ORD
Chicago
$183 Roundtrip, found 3 days ago
$183
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, May 23 from San Juan to Chicago, returning Sun, May 24, priced at $183 found 3 days ago
Sat, May 23 - Fri, May 29
SJU
San Juan
ORD
Chicago
$186 Roundtrip, found 3 days ago
$186
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, May 23 from San Juan to Chicago, returning Fri, May 29, priced at $186 found 3 days ago
Sat, May 16 - Tue, May 19
SJU
San Juan
ORD
Chicago
$200 Roundtrip, found 1 day ago
$200
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, May 16 from San Juan to Chicago, returning Tue, May 19, priced at $200 found 1 day ago
Sat, May 9 - Sun, May 17
SJU
San Juan
ORD
Chicago
$203 Roundtrip, found 4 days ago
$203
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Sat, May 9 from San Juan to Chicago, returning Sun, May 17, priced at $203 found 4 days 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
$125 nightly
The price is $148 total per night from May 25 to May 26
$148 total
May 25 - May 26
Total with taxes and fees
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! (2,664 reviews)
The room was clean, a good size and all the facilities however for me the downfall was their shower. When it was cold it was too cold and hot was too hot and it was difficult to find a happy medium. The bed was fine, but the pillows were too filled and chunky, so my head wasn't supported as much. ...

Reviewed on May 3, 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
$144 nightly
The price is $171 total per night from May 26 to May 27
$171 total
May 26 - May 27
Total with taxes and fees
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! (5,156 reviews)
Staff was very friendly!

Reviewed on May 3, 2026

Opens in a new windowRiver Hotel
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
$216 nightly
The price is $253 total per night from May 23 to May 24
$253 total
May 23 - May 24
Total with taxes and fees
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! (2,274 reviews)
Good for an airport hotel. Definitely dated.

Reviewed on May 2, 2026

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

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
$151 nightly
The price is $180 total per night from May 27 to May 28
$180 total
May 27 - May 28
Total with taxes and fees
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! (4,036 reviews)
I didn’t like the TV app, but everything else was perfect!

Reviewed on May 3, 2026

Opens in a new windowHotel Riu Plaza Chicago
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
$116 nightly
The price is $138 total per night from May 10 to May 11
$138 total
May 10 - May 11
Total with taxes and fees
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! (3,478 reviews)
Staff was wonderful. Great location for exploring the city!

Reviewed on May 3, 2026

Opens in a new windowClub Quarters Hotel, Central Loop, Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
$139 nightly
The price is $165 total per night from May 10 to May 11
$165 total
May 10 - May 11
Total with taxes and fees
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! (4,247 reviews)
I don’t understand the excellent reviews at this hotel. The hotel was in a great location. However the room was very dated and smelled of mildew and mold. Shower was filthy. Furniture was falling apart. Would not stay here again.

Reviewed on May 2, 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
$149 nightly
The price is $177 total per night from May 25 to May 26
$177 total
May 25 - May 26
Total with taxes and fees
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! (2,291 reviews)
clean room, wonderful pool, breakfast was very good, everything felt effortless.

Reviewed on Apr 30, 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
$125 nightly
The price is $149 total per night from May 8 to May 9
$149 total
May 8 - May 9
Total with taxes and fees
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! (10,135 reviews)
The room was ok, no thermostat to control temp and was warmer than i would have liked. The bed was hard and made my back hurt. Staff did not answer the phone for about 30 min between 4 calls that i made before getting extra pillows. The doorman called transport for us and it took forever for him ...

Reviewed on May 3, 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.

Top Picks

*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.