Best Flight From Bradley Intl. To CHI

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Amazing BDL to CHI Flight Deals

The cheapest flights to CHI-All Airports were $223 for round trip flights and $129 for one-way flights in the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Oct 7 - Thu, Oct 8
BDL
Hartford
ORD
Chicago
$223 Roundtrip, found 1 day ago
$223
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Wed, Oct 7 from Hartford to Chicago, returning Thu, Oct 8, priced at $223 found 1 day ago
Sun, Sep 20 - Tue, Sep 22
BDL
Hartford
ORD
Chicago
$224 Roundtrip, found 2 days ago
$224
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Sun, Sep 20 from Hartford to Chicago, returning Tue, Sep 22, priced at $224 found 2 days ago
Wed, Oct 21 - Wed, Oct 28
BDL
Hartford
ORD
Chicago
$227 Roundtrip, found 19 hours ago
$227
Roundtrip
found 19 hours ago
Select Bargain Flight flight, departing Wed, Oct 21 from Hartford to Chicago, returning Wed, Oct 28, priced at $227 found 19 hours ago
Fri, Sep 25 - Tue, Sep 29
BDL
Hartford
ORD
Chicago
$232 Roundtrip, found 3 days ago
$232
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Fri, Sep 25 from Hartford to Chicago, returning Tue, Sep 29, priced at $232 found 3 days ago
Thu, Nov 5 - Mon, Nov 9
BDL
Hartford
ORD
Chicago
$234 Roundtrip, found 5 hours ago
$234
Roundtrip
found 5 hours ago
Select Bargain Flight flight, departing Thu, Nov 5 from Hartford to Chicago, returning Mon, Nov 9, priced at $234 found 5 hours ago
Sat, Oct 10 - Tue, Oct 13
BDL
Hartford
ORD
Chicago
$236 Roundtrip, found 1 day ago
$236
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Sat, Oct 10 from Hartford to Chicago, returning Tue, Oct 13, priced at $236 found 1 day ago

Hotels near CHI-All Airports Airport (CHI)

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$170 nightly
The price is $202 total per night from Sep 10 to Sep 11
$202 total
Sep 10 - Sep 11
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! (10,333 reviews)
"Excellent location, very clean and comfortable room."

Reviewed on Sep 9, 2026

Opens in a new windowCongress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
$152 nightly
The price is $181 total per night from Sep 29 to Sep 30
$181 total
Sep 29 - Sep 30
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, 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.
Opens in a new windowThe Chicago Hotel Collection Ambassador Gold Coast
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
9.4/10 Exceptional! (890 reviews)
"Great spot!"

Reviewed on Sep 7, 2026

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Opens in a new windowKasa Magnificent Mile Chicago
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River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$181 nightly
The price is $216 total per night from Sep 27 to Sep 28
$216 total
Sep 27 - Sep 28
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! (5,409 reviews)
"I didn’t drive in so this was a great location. Staff was friendly. Small room as expected. Met all needs. Main highlight is the location"

Reviewed on Sep 9, 2026

Opens in a new windowRiver Hotel
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

2.5 out of 5
160 E Huron Street Chicago IL
$203 nightly
The price is $242 total per night from Sep 20 to Sep 21
$242 total
Sep 20 - Sep 21
Total with taxes and fees
Book a stay at this family-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
8/10 Very Good! (1,584 reviews)
"The most unique thing about the property was the staff. Everyone we came into contact with were EXCELLENT! The hotel needs a major overhaul!"

Reviewed on Sep 9, 2026

Opens in a new windowHampton Inn Chicago Downtown/Magnificent Mile
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
$224 nightly
The price is $266 total per night from Sep 10 to Sep 11
$266 total
Sep 10 - Sep 11
Total with taxes and fees
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Opens in a new windowHilton Chicago
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
$312 nightly
The price is $371 total per night from Sep 10 to Sep 11
$371 total
Sep 10 - Sep 11
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
9.4/10 Exceptional! (3,532 reviews)
"Close to river cruise and Millennial Park. Room had view of river."

Reviewed on Sep 9, 2026

Opens in a new windowHyatt Regency Chicago
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
225 N Wabash Ave Chicago IL
$311 nightly
The price is $370 total per night from Sep 27 to Sep 28
$370 total
Sep 27 - Sep 28
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Opens in a new windowL7 Chicago by LOTTE
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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.